I told him about my recent break up and his advice was simple – get out there and start dating/interacting/sleeping with more women. His philosophy is simple – by dating and sleeping with a lot of women he’ll eventually find the one that “sticks” and the one that he’ll settle down (not settle) with.

We were at a bar but there weren’t that many attractive women to approach there so we just continuing chatting. It was getting a little chilly and the bar put out these really cool heat lamps that emanate a warmth from them. I was really drawn to the lamp and got up to stand close to it. It just so happened that next to the lamp was a table where a guy and a very cute girl were sitting. It didn’t look like they were a couple – just friends. The girl looked up at me as I came over to stand by the heat lamp and I opened with something really simple like “man it’s cold here – and it’s so nice to stand by this lamp”. She responded really well by saying how where she’s from the winters aren’t as bad as here. Then we started talking and bantering about the weather and how we were both originally from he same part of the world. I talked a little bit with the guy, too, and it was like I had this instant connection with a complete stranger just from standing by a heat lamp.

After about five minutes of talking to her I excused myself and went back to my table to join my friend. Later on, as we were leaving the patio, she waved good-bye to me and I said bye to her. Pretty cool spontaneous interaction. I feel like I’m getting more and more back into the swing of things

I was running and spotted a cutie walking towards me. She came out from an adjoining path so it was a bit of surprise. I hesitated and didn’t stop to talk to her. Unlike before, I didn’t beat myself up. I just figured I’d approach another one today. Sure enough, later in the day I had to go grocery shopping and that’s where I got a chance to really exercise my pick up muscles.

Approach #53 – Grocery Store – Woman by the Grapes

I first briefly talked to a lady by the grapes. She wasn’t great looking, just average, but I wanted to interact with at least one woman today. As she was standing by the grapes and looking over them, I just walked up casually next to her and asked her if the grapes were any good. She said they seem to be and then I asked her if she sampled any. She said she hadn’t so then I pretend she was being really bad by saying “I thought EVERYONE samples grapes in stores” and gave her this look like “It’s OK – I won’t tell on you if you do it.” So she went ahead and sampled the grapes and told me they were quite good. That made me feel better – like I was very slowly getting back into the “not caring” mindset I was at before.

Approach #54 – Grocery Store – Hot Customer

While I was standing there, thinking how good I felt, I saw this very attractive woman walk right past me. I just saw her pass me and admired her figure but felt immobilized to go and stop her to talk to her. So I continued walking up and down the aisles, making short conversations/comments with women I’d pass in the store. Then, as I went into the next aisle, I noticed the woman that walked right by me before. She was standing by the tea section and trying to figure out which one to get. Now, I’m not a huge tea drinker and I wasn’t planning on buying any tea. But since she was there, I just made my way towards her and opened with “Which one’s a good one to get for very special guests?” She smiled at me and gave me a few options. We bantered for a couple of minutes about what teas are good to get depending on which types of guests you’re having (pretty silly topic of conversation but it was fun). I noticed she had an accent and I asked her about it. Turns out she’s from the same country I’m from (except I don’t have an accent). She was quite surprised at our commonality and we talked for another minute or so. After a while, I didn’t say any more – not because I was getting nervous – but because I felt I had done what I wanted to do. So eventually she excused herself and continued her shopping. I felt good for just walking up to an attractive woman and starting to talk to her.

Approach #55 – Grocery Store – Cashier

As I was checking out, I made sure to go the cutest cashier I could find. But as I was about to start putting my groceries on the conveyor belt, she said she was closing and directed me to another cashier. I made this mock refusal saying I wouldn’t leave and that she would have to ring me through – she could tell I was joking and we exchanged a nice moment of connection.

I went to the cashier that rang me through and I ended up bantering with her, too! I let this old lady go ahead of me who only had a few groceries and this was a topic of conversation between the cashier and me after the old lady left (the old lady didn’t speak a word of English – luckily both of us spoke her native language). I talked with the cashier about where she grew up, when she immigrated to the country. I even told her that if she was a bit older I would’ve asked her for her phone number. That made her smile and I could tell I probably made her day. As I finished packing my groceries I told her bye and it was like we were friends now.

I’m really beginning to get back in the groove with this. I’m wondering if I should approach one woman a day – not to necessarily ask her out, or even talk for a minute. Just to say something to her – so I can get used to starting conversations with women in public again.

Well, today’s the day my approaching women challenge is due. I’m happy to report that I accomplished the challenge – I approached 50 women (51, actually). Even more, I’ve recently started seeing someone that has a very good chance of developing into something serious.

I’m feeling pretty good. All the practice that I did with my daily pickup practice (saying hi to strangers) and my approaching women challenge has really helped me open up socially and attract the kinds of women that I really want to be with. For the guys out there that want to improve their social/dating skills – I recommend doing something similar that stretches your comfort zone. I feel like my new skills have become integrated into my daily life. I’m not really trying to pick up women anymore. It’s evolved into having regular interactions and conversations with strangers – as the opportunities arise. Life is just more fun that way.

I’m going to post my past approaches that I’ve done on my way to 50. I stopped posting them regularly because there were just too many developments to write about at the time.

I’m not really sure where to take this blog from there. It’s not my goal to be eternally single – I knew it would be a temporary condition. I’m not going to post details of any serious relationships. So at this point I’m not sure what I’m going to do.

I ended up meeting someone and things got serious. In fact, I really thought she would be the Mrs. Right for me. She was one of the women that I met in my dating frenzy from a few months back. Anyway, we really hit it off and I thought I would retire the Dating Guy (it was never my intention to be a constant dater). But, alas, things didn’t go as planned. The issue? She wasn’t as into me as I was into her! So here I was, after all the practice of approaching women that I had done from April to June, feeling pretty hurt and emotionally vulnerable – in a way that I hadn’t felt in a long time. Don’t get me wrong – we had a lot going for us – we were very compatible and had a great time with each other. She even told me that I was perfect for her and I’m everything that she was looking for. But she couldn’t explain this feeling she had that made her hesitate about going further with me emotionally. I tried to wait for her to come around, but after numerous attempts, I just felt that this issue would keep haunting us and we broke up. She still very much wants me in her life but I haven’t decided yet if I want that.

And yes – I did tell her about the blog – but I didn’t tell her about the URL. I told her about my Approaching Women Challenge – I was very open with her. She was very cool about it, which made me like her that much more. I just didn’t feel that it would be appropriate to post my ongoing dating life details about someone I was seriously involved with. Hence the silence from me in the last couple of months. I apologize to the people that were beginning to wonder if I’ve disappeared from the blogosphere without bothering to even say a proper good bye. I was just waiting to see how things would pan out with us.

So, I’m back to the single life again. Sigh… It’s been about a week and a half since we broke up and I think I’d like to start getting out there soon. I’m seriously thinking about starting to approach women again. In fact, I tried to do it again recently but found it more difficult than before – I’m out of practice! Yes, I must admit, this is NOT like riding a bike. At least not in the beginning. I want to get comfortable (and stop caring again) starting conversations with women in public. I haven’t decided if I’m going to make a new challenge for myself.

Approach #52 – Bookstore

I went to a bookstore tonight and tried to start conversations with women there. I only managed to start one. The rest I hesitated on and didn’t do anything. And the one that I started wasn’t that great. I went to the cooking section and asked a women there if she was reading anything interesting. She said she was really into cookies and was reading a cookie recipe book. I asked her if she’s obsessed with cookies (perhaps not the best question to ask a woman – since many are very weight conscious) and she said she was, but began to slowly walk away from me. A few seconds later I noticed a guy join her so she was obviously there with someone. Ah well… you gotta start getting back on the horse somehow – this was my first approach in over 2 months! I think I’ll start to get back in the groove as I keep getting out there again.

I feel that I need to get back into my former headspace because that’s what caused the abundance of high quality women to come into my life last time – and this was without any Internet dating. I felt confident, relaxed, loose, etc. And I want to feel that way again before I seriously start dating again. I want to get back into the headspace that really worked well for me last time – and find Mrs. Right.

I talked to one of the women my friend set me up with and we made plans for this week. So now I’ve got four dates coming up with four different women plus another one I’m supposed to call. Are you confused yet?

Woman #1 stood me up. Well, technically she cancelled about half an hour before we were supposed to meet. She called me in a distressed voice saying she wasn’t going to be able to make it. I was a little… um… surprised. I asked her if everything was OK but she didn’t want to get into it. She said she’d call me back but never did. Man, that was quite rude. After getting over the initial disappointment I felt happy that this woman showed her true colors so quickly – that she’s a flake that doesn’t have her sh*t together. This is someone that a friend of mine set me up with so it was going to be a blind date.

Woman #2: we had an amazing date – really really connected. Definite attraction there. We went for a long walk in a park, then grabbed a bite to eat, then she invited me home to her place – and nothing happened. I didn’t want to make this into another opportunity to get some “action”. That’s not where I’m at these days. We just hung out and talked and connected even further at her place. A really great date and we made plans to go out again next week.

Woman #3: had a really good date with her, as well. Didn’t connect with her as deeply as with Woman #2 because Woman #3 is more introverted and cautious when meeting new people. But we definitely have common interests and the physical attraction is there. We did a lot of bantering – all that bantering from pick up practice comes in handy in situations like this. We also made plans to see each other next week.

Woman #4: haven’t gone out with her yet but we’re confirmed to get together in a few days.

I feel pretty good but I’m a little stressed about the “what if” scenario – what if I end up really liking more than one woman and won’t be able to choose. Sure, some people might think this isn’t a bad problem to have but it’s got me a little worried. I’ve already set up second dates with Woman #2 and #3 and this is before I’ve gone out with Woman #4.

Overall, I’m quite happy that I’ve now got choices with women of this calibre. I would call the women I’ve recently gone out with “high quality” women – i.e. physically attractive, share my background, share my values. I think I’m heading in the right direction.

I’ve been at a few recent social events lately – a few parties and a speed dating event. I’ve been asking out and interacting with a lot of women – I haven’t had the time nor inclination to write about all the interactions. But in a nutshell – I have four dates lined up. Three of these women I met at a speed dating event and the other one a friend of mine set me up. The three from speed dating I’m really attracted to and we really hit it off on our speed dates as well as the phone conversations thereafter. With the blind date setup, we really hit it off as well, but it’s all been over the phone so I don’t know how I’ll feel about her when I meet her in person.

The bigger picture in all of this is that I’ve decided to get “serious” about finding someone. Whereas before I sometimes entertained the notion of getting really good at picking up or partying it up with different women, I don’t feel that way anymore. I simply want to find the one right woman for me that I can settle down with.

These four dates are all coming up in the next few days – wish me luck!

While I was running in the park, I bumped into Heather, the woman I approached the other week while running. She was walking with a group of people – looked like she was doing another training session with them. I said hi to her and her group and we talked for a few seconds. There were four of them all together. Three women and a guy. The guy didn’t look like he was with Heather and it turned out one of the women was his sister.

I didn’t stop and interact with Heather further and just continued running. Now that I’m thinking about it, I can’t help but kick myself for not pursuing her further – I could have said something like “So when can I run into you again?” and see if I could get another time we could talk further.

On the way home, I noticed this woman walking ahead of me on the sidewalk (away from me). She looked really good from behind as I was approaching her but when I turned around, she wasn’t as attractive as I had hoped (5). Doesn’t matter – by then I had made the decision I was going to go for it (like one of those missiles that’s been fired – once it’s fired, you can’t bring it back).

I say hello as I pass her – in a friendly way.

I run to about 10 feet ahead of her, stop, turn around and say, “How are you?” – still being friendly and upbeat.

“Fine.” I thought I detected an accent – maybe English isn’t her first language.

I go into my banter – something I thought of trying previously:

“I’m doing a survey for the city, and we’re talking to all the beautiful citizens of our city to find out how we can improve our streets.”

She’s not quite sure whether to play along or if I’m serious. She doesn’t answer much at first and I thought I would have to jettison this approach pretty quickly. But then she starts talking and we get a conversation going. I ask her what she does and how long she’s been in the country. Turns out she’s a caregiver for a family and has lived here for four years. I ask her if she has a husband (I don’t know why, but she seems like the type to have a husband) and she says she doesn’t. So then I start joking with her that in addition to my other 2 jobs (running and taking surveys for the city), I’m willing to take on the task of finding her a husband. We have a great time laughing about this and I feel I’ve made a real connection.

After about 5 minutes of walking with her, I decide it’s time for me to run home so I tell her it was great to meet her and wish her all the best.

I continue running for home and spot a really attractive woman walking up ahead of me with a baby stroller. I’m approaching her from behind so I try and be really easy going, so as not to startle her. It works, she responds very warmly to my “hi”. I then ask, “Is that your baby?” (I wanted to be really sure that she was unavailable, OK?!) and she says that it is. I then say, “She’s really lucky to have you as a mother.” The woman smiles really genuinely and I can see that I probably made her day. That felt good! And I didn’t even ask her out. I like making women feel good!

When I get very close to my building I spot an elderly woman. I’ve started to do my cool-down walk by this time and as I pass her (she’s walking in the same direction as me) I say a warm hello and ask her how she is. She answers very warmly and I somehow get into a conversation with this woman (I’d say she’s in her 80s). She’s funny, too! One of the first things she tells me is, “I’m too young for you.” I’m bantering with an octogenarian! Hilarious! We end up having this really great talk for the next 10 minutes – she gives me all this advice about what kind of woman to look for. How the woman has to have her own career and know how to work and not just depend on me to give her money (all things I agree with but it was nice to hear this coming from someone a lot older than me).

I’m genuinely grateful that someone a lot older and wiser is sharing with me their wisdom. At the end, she thanks me for stopping to talk to her and tells me how it’s not often people of my age stop and talk with people of her age. I thank her for sharing her wisdom and I go home feeling great.

Things I Learned

• It’s not about pick ups – it’s about making connections with people. I’ve had numerous interactions like this that I haven’t blogged about – spontaneous conversations with people that I had no interest in picking up. But it was a worthwhile interaction and rounds out my social skills.
• Banter is a great way to see if a woman has a sense of humor. The woman I approached wasn’t a native English speaker but because we were bantering, it made it easier to connect with her and to see that she was someone fun.

List of All My Pick Up Approaches

When I started this whole pick up practice and approaching women challenge I really wanted to get over the anxiety I felt when I would see a woman in public that I wanted to approach. Well, I can now say that that anxiety is mostly gone. I feel pretty comfortable approaching women in most situations.

You would think I would feel great about this and part of me does. But there’s another part of me that’s left saying, “Yeah, so now what?” It’s like the prize I so dearly coveted turned out to be not that great when I got it. Most of the women that I approach are either not interested or I find out after talking to them for a few minutes that I’m not interested in them. There’s also the issue of finding someone with the same background as me and doing that with random strangers doesn’t help the odds.

I was talking to a female friend of mine and I compared all these pickup approaches to gorging myself at buffet – where I try and sample every different dish at the table and end up feeling sick afterwards. She suggested that I, instead, take my time savouring each dish – I like that analogy.

Now I could devote myself to improving my pickup approaches – really connecting with attractive women that I meet in public. I could also practice at different venues (clubs, shopping malls, bars). The truth, though, is that I’m not sure that’s what I want to do. I think the approaching women challenge served a purpose and now it’s time for me to move onto the next stage – meeting high quality women in other ways. My goal, after all, is to meet the right woman to start a serious relationship with. The pickup practice is just a tool to get me there and not an end in itself.

I’m going to continue approaching women and posting my pick up approaches – after all, I have my approaching women challenge to complete. I’m up to 39 approaches already so I’ve got 11 more to go. But I’m going to slow down the frequency of the approaches and focus more on meeting women through other avenues – through friends and social events.

I feel like all the approaching I’ve done in the last couple of months has served a really important purpose – I’ve learned how to be relaxed and banter with women (and people in general) I just meet. Now I can take those skills and apply them to “normal” social situations.

As I’m walking towards my building I spot an attractive woman walking towards me, by herself. I figure it’s time for another street approach – since I’ve got a lot to learn from my last street approach.

As she gets within talking distance I just lift my arms up and say in a carnival like tone, “I just have to stop you!”

She just looks at me like I’m some weirdo and keeps walking. I say, “Hey, where are you going? You’re walking out of my life for good.”

She just keeps walking and doesn’t stop.

OK, so you’d think that was a total rejection, but I’m actually smiling with myself at this point. I’m getting over the fear of approaching women on the street. Sure, she thought I was some weird lunatic, but that’s beside the point. I know I’ll get better at this.

I’m feeling almost giddy and say to myself, “I’m getting drunk from approaching.” and I almost start to walk a little funny. But I recover and notice this really nice old lady sitting in one of those walker/chairs right on the sidewalk.

I say hello to her and we end up having this great chat as I keep her company while I walk her to her building. She thanks me for talking to her (I don’t have a problem starting conversations with the elderly) and I think I just made her day.

Things I Learned

• Doing something is better than doing nothing. Even if I get completely rejected, it’s better than getting nervous and not approaching at all.
• Being a little zany/wacky scared her off. I’m wondering if approaches like that work better at the bookstore where there’s a feeling of more safety for a woman than out on the street. Perhaps I need to tone it down a little for street approaches.

List of All My Pick Up Approaches

I start walking over to her and say something really interesting like, “Hi.” I’m pretty relaxed because I’ve just finished my run so I’m feeling tired. But I’m also confident and easy going because I just that great approach while running.

“So what are you studying?”
“Physics.”

She smiles but isn’t as responsive as I would have liked. I think of something to banter with:

“I used to tutor in physics. I’ll tell you what – I’ll give you a special rate so I can tutor you.”

She just smiles a little awkwardly – not sure that had the desired effect I was going for.

As I’m about to give up on her I hear my name. Turns out a friend of my sister was close by and she heard me chatting up this woman. So for the next few minutes I talk with my sister’s friend.

When I head off from the coffee shop I say good-bye to the woman studying physics and wish her well.

Things I Learned

• Banter with something more inclusive. If I offered to tutor her, what was she going to say? Maybe she was just not interested but if I suggested instead that I needed help in physics and she could tutor me that might have worked better.
• Getting a neutral response from a woman isn’t that big of a deal. I’d rather get a neutral response or get totally rejected than not approach at all and then beat myself up for not following through.

List of All My Pick Up Approaches

As I’m kicking myself for not stopping, this really cute Asian woman (7) starts running next to me from an adjoining path. She just happened to have started running at the time that I was passing her. I just said the first thing that came to my mind:

“You going to run with me?”
It was a fun, playful thing to say.

She replies with “Sure, why not.”

She was wearing an iPod but takes it off the headphones so we can talk. We continue running together through the park. I start bantering with her. I’ve never done this WHILE running. Usually I stop to talk to women that are walking.

She tells me she hasn’t run for a year and I tell her she looks very good for someone that’s supposedly out of shape. I find it easy to put in compliments like this while we’re bantering – it just flows more naturally.

I joke with her some more – role playing that she’s my trainer and I’m the one that needs help with my running. I even mock myself by starting to run as if I’m very old and she laughs.

She tells me she’s new to the area and only lives five minutes away. I joke with her that I’m going to give her a fabulous tour of the neighborhood and that my limo is parked where she started her run. She asks if there’s any champagne inside and I say “Of course.” I ask her if she likes caviar and then ask her if she prefers red or black. We just have fun laughing and joking around with silly topics like this while we’re running and it’s just a great way to spend the afternoon.

We stop to rest a few times and we end up talking more, getting a chance to connect further. She even agrees to run with me past the point where she started. At one point I thought she suggested that she run with me all the way back to my building but then when we get to the end of the park she says she’d better stay in the park. I make no big deal about – no whining, no convincing her to keep running home with me. I just say “no problem” and we rest for a few minutes and talk some more.

Finally I tell her it was great to meet her and start to get ready to run for home. I can sense some hesitation in her voice as we’re saying good-bye. I think she was wondering if I was going to ask her out or not. But I decide no to. I wasn’t as attracted to her as I would have liked. Also, this might sound shallow but it’s true – she was a 7 and I want to date 8 or higher.

Things I Learned

• Focus on bantering and having fun instead of asking her out. By doing that a few interesting things happened – she introduced herself to me, she wanted to keep running with me, she wanted to take breaks with me. We were having a great time and there was no pressure committing to a date or giving me her phone number. She felt comfortable doing all these things because we were both having fun – that’s it.
• Not asking her out made me feel really empowered. Just because she was attractive didn’t mean that I automatically wanted to go out with her. It would have been very easy to ask her out at the end of our interaction and I think she would have said yes. But it’s more important for me right now to get more comfortable meeting and building connections with women than dating. This might sound strange, but I feel I’m too busy improving my approaches with women to worry about dating right now. This is not a permanent condition.

List of All My Pick Up Approaches

The biggest realization about the importance of banter came after this approach – we ended up just having fun – chatting, laughing, connecting and flirting – most of it AFTER she told me she has a boyfriend. This was a very important approach in my ongoing development.

Fresh from my bantering with the bookstore clerk after my last approach at the cooking section, I was feeling better and upbeat. I walked around the store and spotted a definite babe (7), by herself looking around the philosophy section. I decided to move to the aisle next to the one she was in so because she looked like she was scanning and I wanted her to come to my aisle so I can open the conversation. But she stopped at the end of her aisle. Then a male store clerk comes over to help her.

“Can I help you find anything?”
“No, thank you.”

He goes away and I spring into action. I pretend I work at the bookstore and put on a tone of mock authority:

“Can I help you find anything?”

She looks at me – I’m obviously not a store employee so she smiles and the interaction begins:

“No, thanks you. Wait a second… you don’t work here!” (big smile)
“How do you know? Maybe it’s my day off.”
“Yeah, right. You don’t look like you’re the type to work here.”
“Oh, really, so now you’re making judgments of me. I was going to help you out but now forget it – you lost your chance.”

I start to walk away in mock anger and she starts to laugh. We continue this interaction for a few more minutes. Then she introduces herself to me and brings out her hand – Melissa. That’s never happened to me before. Usually, I’m the one that initiates the introductions. We spend the next half an hour bantering, flirting and just having fun. At one point I tell her:

“I don’t know why, but I’m drawn to you. It’s not just because you’re good looking – because there are other good looking women around. But there’s something more there.”

She replies with a sarcastic “thanks” about the backhanded good looking compliment but I’ve definitely got her interest and I can see she’s still smiling and really involved in our interaction.

OK, I have to admit – I stole that last line from a video of a pick up artist named Mystery (it’s towards the end of the video). I’m experimenting with banter right now – it’s like a whole new world beyond the boring “resume” questions (e.g. What do you do? Where do you live? What do you like to do?)

We continued talking and bantering till the store closed – it was great. First I helped her find her book then she followed me to the section that had my book. If you saw us, you’d think we were together – seriously. And yet we didn’t know each other at all less than an hour ago. Amazing. A whole new world of possibilities is opening up for me.

There were a few times when we casually touched, too. When we were both looking for her book on a shelf, our hands brushed against each other. Or when I was joking around with her and touched her elbow for added effect. Here I was touching a woman that I just met and she didn’t mind and wanted to continue interacting. A whole new world is opening up to me

I suggested a few times throughout our banter that we should go and grab a coffee – I think too many times to be perfectly honest. I should have played it more cool and just gone with the flow. She refused all three times but continued to stick around – she was obviously enjoying herself but didn’t want to commit to going for coffee. After all, she did say she has a boyfriend.

As the store is closing, one of the store clerks is helping me find my book while Melissa went to pay for her’s. She comes back to me and wants to say good- bye. I get this exaggerated disappointed look on my face and then suggest one last time that we go hang out for coffee. She says she can’t but she had a great time. She puts out her hand and I shake it and then give her a big embrace. She’s really into the hug, too – it’s not one of those pity hugs that women sometimes give (I really hate those). I think we really connected. And with that, she walks out of my life.

Things I Learned

• Opening the conversation with something fun and non-threatening really worked! I didn’t do a straight “I find you attractive and had to talk to you.” I also didn’t do a lame “Do you have the time?” type of approach. It’s like there’s this magic sweet spot in the middle – between fully direct and fully indirect.
• Don’t ask her out so soon. I did the same thing when I picked up Anna at the bookstore who also refused to go for coffee but stuck around to talk until the store closed. I asked Melissa to go for coffee three times – way too much. Sends a needy vibe to her that was totally unnecessary. Instead I should have just continued the interaction and only suggested we do something at the very end, when the store was closing. The great thing is that because we were having so much fun bantering she stuck around even though she mentioned having a boyfriend and after turning down my multiple coffee requests. Women like to feel comfortable being accepting a coffee date. It was safe for her to continue talking to me in the bookstore but going for coffee would have increased her commitment to the evening – something that she would feel comfortable doing after we spent more time bantering. Just by bantering she introduced herself first instead of me having to do it. That’s a sign to me that she felt comfortable and was having fun and wanted the interaction to continue.

List of All My Pick Up Approaches

First Missed Opportunity

I stopped off at the bank machine before going on the subway. As I open the door to go inside, this hot babe walks out right in front of me – by herself. I hesitate and do nothing. Damn it. I thought I was feeling more on top of my game but I’m realizing it will take many more approaches to feel comfortable opening a conversation in a situation like that.

Second Missed Opportunity

As I’m descending the stairs to the subway, I’m trying to stay positive and think of how relatively well the banter went with the woman walking the dog, at the end of my run today. Then I see another hot babe walking up the stairs as I’m coming down. What do I do? Absolutely nothing. Man that totally gets me in a down mood.

Third Missed Opportunity

After a few stops on the subway, this attractive woman gets on by herself and sits a few seats down. Maybe 20 feet away. What do I do? Do I come over and start to banter with her? Nope. I do absolutely nothing.

Fourth Missed Opportunity

Finally, at the bookstore, I feel like I’m more in my element. I don’t want to use it as a crutch, though. I want to be comfortable approaching women in a wide variety of venues. Well, as soon as I come in I notice another attractive woman by the magazine section. But I’m not feeling very confident after all my previous missed opportunities so I just pass her by and walk up to the second floor where I can get more in my element.

The Approach – Finally

I spot an attractive woman by the cooking section and I can feel myself getting nervous. But I feel like if I don’t approach her I’m going to go into some kind of mini-depression for being such a wuss and not taking any action. So I muster up the balls and try to casually walk up beside her. She’s glancing through a cookbook in her hand.

“Man, what is it with all these cookbooks? I just want something really simple.”
She looks up at me and gives me a sympathetic smile and replies with something neutral. I glance around the cookbooks for a few seconds and say something else about how I just want a simple cookbook that a novice can use.

We have a somewhat stilted exchange for the next few minutes and she eventually leaves. OK, I got over my approach anxiety hump. I’m feeling a lot better now.

Bantering with the Bookstore Clerk

Throughout my interaction with the woman, the female bookstore clerk was just listening in passively. After the woman left, the store clerk turns to me and says, “Do you need help in finding something?”

I get this big grin and mischievous look on my face:

“Oh, I don’t know if you want to help me. You might regret it later.”
“Well, I’ve been writing a haiku here for the last few minutes, I’m a little bored and I’m just looking to help someone.”
“You’ve been writing haikus instead of working like you were supposed to? I think I’m going to have to tell management about this – they’ll probably fire you.”
(mock fright) “Oh no! You wouldn’t!”
(mock conviction) “Oh yes! I would!”

Then we have another playful exchange where I tell her that I’ve got “a friend” that doesn’t know how to cook and wants to learn and how I’d like to help my “friend”. She plays along and emphasizes the word “friend” and gives me a flirtatious eyewink every time she uses it. We have a great time just playing and flirting like this for the next 10 minutes while she helps me find a cookbook.

In the end I decide not to ask her out – she’s cute but not as attractive as I would like, so I decide it’s time to look for more women to talk to. The bantering, though, is something I’m discovering has an amazing effect – and I ended up using plenty of banter in my next approach that turned out to be the best approach of the day.

List of All My Pick Up Approaches

The woman was walking her dog towards me so I get about 10 feet away from her I before I stop running and let out this big, “Whew! I need to stop!”
She looks at me in a curious way.

I just look at her, get this big smile on and tell her in a playful way, “You gotta tell me something – anything!”

She smiled back! No deer-in-head-light look!
She replies in a playful way with a big smile on her face, “What do you want me to say to you?”
“Tell me something – anything!” I keep smiling in a playful way.
“Um… how are you?”
I try and keep it playful but just say “I’m great – how are you?”
“I’m fine.”
She continues to smile but isn’t quite sure where this is going. I bend down towards her dog and ask her the name. She tells me and I play with him for a little bit. But after a few seconds her dog starts pulling her away from me – maybe the dog got annoyed and wanted to continue his walk. She lets the dog pull her away and after my futile attempt to get her to stop walking away, she’s gone.

Things I Learned

• Being more fun and playful with her made her feel at ease. It feels less dangerous and creepy than a “I find you interesting and had to talk to you” approach that I’ve used in the past. She didn’t get the deer-in-the-headlights look like my last approach while running. This was really the start of a huge concept that I’ll be posting more about in future approaches – banter. It was my first introduction to the concept of bantering with a woman when I first meet her and it started to open my eyes to the possibilities.

List of All My Pick Up Approaches

I was out on my daily pick up practice walk and as I passed a bus stop I noticed an attractive woman waiting inside the bus shelter. She was putting her hair in a ponytail while waiting for the bus and she was the only one waiting at the bus stop. As I passed her, we locked eyes – perhaps a little too long. I hesitated – I should have just gone for it right there but I continued walking and didn’t approach her.

About half a mile after I passed her I decided to go back and approach her. As I’m heading back I saw a woman walking on the other side of the street so I cross over so I can say hi to her. But the woman crosses over the street right after I cross over to her side of the street (did she get scared that I crossed over to her side?) Then I see a woman walking her dog and I was going to say hello to her. I was even going to stop and talk to her (once she got closer so I can tell if she was attractive or not) but she started heading off in another direction. Damn it – I began to lose my confidence.

I was getting closer and closer to the original woman at the bus stop. She was now standing outside the bus shelter still waiting for the bus. As I got within conversation distance I stopped close to the bus shelter and just said “Hi” to her.

She didn’t say a word but just stared at me – maybe in that “Oh my god, what’s he going to do?” type of way.

I said, “Hi” again and she continues to just stares at me but now with a “What do you want?” expression.

I say, “How are you?”

She doesn’t say a word but perhaps moves her chin an inch.

I finally just say, “I’m just saying hello.”

She’s now sort of glares at me – like in a “What the hell do you think you’re doing?” type of way. In a nutshell – she’s clearly not interested in interacting.

So I decide to move on and continue walking. I shake my head a little at this woman’s intense reaction. Maybe she was having a bad day. It reminded me of thirteenth pick up attempt where the woman completely ignored me at the coffee shop.

I tried to shake off the sting from her rejection by continuing with my walk and saying hello to people, which helped. I feel I need to improve my street approaches.

Things I Learned

• Staring at women is not cool. It tends to scare them and put them on the defensive. When I was passing her by and she saw me through the bus shelter glass, I think I stared at her too long. Who knows – maybe I looked like some hungry puppy or something. Not the impression I want to have on her. I think that made her more defensive and cold to my approach when I came back around the second time.
• Getting completely and utterly rejected by a woman isn’t that big of a deal. Sure, it stung a little and I felt like she totally misjudged me and my intentions but I also thought she was a cold fish that wasn’t open to sharing a new experience. Her loss – she missed out on a fun interaction.

List of All My Pick Up Approaches

By the time I got to the bookstore it was only about 20 minutes before closing so I just started walking around the aisles and looking for women I could approach. No nervousness, no hesitation, just a focused determination to approach a woman (maybe, I’m getting too determined at being relaxed around women).

As I’m walking in one direction I spot a potentially attractive woman walking in the other. I don’t hesitate. I turn around and start walking towards her. She stops at the kid’s books section so I walk over. I don’t even try to hang around her for a few minutes or anything. I just say something off the top of my head like, “I just love kids books.” She responds with something nice like, “Me, too. I love shopping for them.” I ask if she’s a grade school teacher and she says she is.

“Grade one?”
“No, grade two.”
“Awww, that’s nice.”

She seems nice and friendly. Attractive but not on the high end. I’d say a 6.5. That’s OK – it’s still worth it to talk to her. We talk for a while longer about the books and I think of this one kids book that my ex-girlfriend told me about. I’m describing it to her because I can’t remember the title. I thought since she’s a grade school teacher she would for sure know it but she just stares blankly at me and doesn’t recognize the book from my description. Ah, well. After a few minutes of this interaction I just stop talking. Not because I’m nervous. Not because I don’t know what else to say (I could think of some other topics if I was really interested). Just because… I feel like I accomplished my goal – talking to a woman in public for at least a minute and I decide I’m not interested in asking her out. So I’m done. Soon enough she says, “Well, I’m heading off. It was nice to meet you.”

If I met her online, that whole realization could have taken hours of emailing, talking on the phone and going for the perfunctory coffee date. Man I love meeting women in public over Internet dating.

I then proceed to walk around the rest of the bookstore to see if there are any other women I can approach. It worries me a little that I’m beginning to make this almost mechanical, like a robot walking in that stilted way with the robotic voice “I must approach more women. I must approach more women.” But I think this is a necessary stage that will soon pass. I’ve already gotten over the initial fear of approaching a woman totally cold so now I’m evolving my skills. I don’t spot any hotties in the bookstore so I walk over the attached Starbucks coffee shop that’s attached to the bookstore.

I don’t see any women I could approach there either but I suddenly notice my friend Yvonne there! She’s in her business suit and talking to a client at one of the tables. My instinct was to do a mock approach with her in a fake French accent like “Hi, I couldn’t help but notice you sitting here and I just had to come over and say hi. Your eyes are like a the sparkle of a blue ocean.” She’d find it very funny and we’d have a hoot catching up but I just didn’t think that would be appropriate with her client present. So I just tap her on the shoulder lightly and say hi. She’s very happy to see me and we talk for a few seconds before I excuse myself so she can finish up with her client.

I wonder around the bookstore and chat with some of the cute female staff (too young for me) but I don’t see any women I can approach. It’s funny – I see a cute store clerk standing by the aisle and I just come over and say “Hi” in a friendly way with a smile on my face. She says hi back and is ready to help me find a book. But I just stand there smiling at her. After a few seconds of her waiting for me to ask her my book-finding question that never comes, I just say, “I just wanted to say hello, that’s all.” She smiles in a friendly way and says, “Oh, I thought you wanted me to help you find a book.” and starts walking away. That exchange might sounds weird, but I’m learning to stretch my comfort boundaries. The nice guy inside me needs to stretch his boundaries and be OK with not following societal conventions all the time. As she walked off, I smiled inside feeling that I didn’t care that much if she thought I was a little weird.

As I come back to the coffee shop to check if Yvonne is finished with her client, I see she’s not there. As I’m about to head back into the bookstore I hear my name (Dating Guy! Dating Guy! ) and as I turn around I see it’s a woman that I know from high school – Emily. Amazing – I ran into her a couple of years ago when I was still with my ex-girlfriend and from what I remember I think she was with someone at the time, too. But last night she was there with what looked like a couple (can’t tell for sure because they weren’t holding hands or anything). So it was just the three of them. We start catching up – I’m feeling pretty upbeat and friendly so that was nice. As we’re getting ready to part she asks if I have her email and I tell she’d better write it down for me so she does. It was great to see Emily and she’s definitely cute. She was wearing kind of frumpy clothes, though, so that made me wonder if she stopped dressing nicely (never know who you’ll bump into ) but we’ll see what happens.

I ended up finding Yvonne who was browsing books with her client, who turned out to be a good friend of hers, too. The store was closing up so we ended up having a blast just catching up in the parking lot. Yvonne now knows about my new picking up and approaching women practice (but not about this blog) but we couldn’t really talk about her latest dating adventures nor mine since her friend was there. Things with her are really great – there’s no awkwardness at all even though I made a move on her previously.

The amazing thing about tonight is that by just going out to meet women I ended up connecting with two other people that I know. I would have been just as happy just doing my approach in the bookstore and then going home but meeting up with Yvonne and Emily was the icing on the cake to a great evening. The amazing thing is that it just came about out of thin air – I didn’t email or call anybody. I just decided to be more social and talk with a few women and I ended up having a blast. I’m stoked to complete the rest of my approaching women challenge.

Things I Learned

• I’ve noticed that I didn’t try as hard to keep the conversation going with the last two women I approached. Maybe it’s because I reach my one minute conversation goal fairly quickly and then I have no motivation to continue. I also think I’m getting more picky. My last two approaches were with women that while being cute, I wasn’t immediately drawn to them. I don’t feel the need to continue talking to them, then asking them out, then going out on a date or two with them, and then deciding I’m not as attracted to her as I’d like to be. Been there, done that. Of course, watch me totally screw up my next approach with a woman that I think is totally hot.
• Meeting women in public is a great catalyst for being more social. This is something that I’ve talked about multiple times before but it’s worth mentioning again. Out of thin air, I created a fun evening by meeting a couple of women and bumping into two other women I know.

I went out running last night to wind down after the work day and to practice talking to women. I was feeling rather relaxed about that part and yet somehow determined. I think setting up the approaching women challenge and standing to lose $50 has really crystallized my focus on getting this goal accomplished.

I start running and, as is usual for me now, start saying hello to virtually all the people that I pass. I know this might sound like a trivial detail but I think it’s important: the quality of my hello’s and hi’s has been improving. If I’m feeling more shy/introverted I would say hi in a more neutral way. Also, I’d say it as I was just about to pass the person so I wouldn’t get a chance to see their reaction (lest it be a negative one). If I’m feeling shy I would often skip saying hello to people I’m passing from behind. But lately I’ve been noticing that my hello’s have been improving – I say it in a more friendly and open way. I usually smile when I say it. And I say it a good 10-20 feet in front of the person so I can see their reaction. It’s a little thing but it’s a good indicator that I’m getting more and more comfortable talking with strangers.

I have this determination in my head – I will talk to the first attractive woman I see. I will talk to the first attractive woman I see. I will talk to the first attractive woman I see. I can’t say I’ve ever felt this determined and sure of myself before. I don’t spot any hotties on the way to the park but I’m still feeling pretty upbeat. I’m hoping I run into Heather, who I almost picked up last week.

About five minutes into the park I spot a couple of women walking up ahead. The one on the left has a nice backside and the one on the right seems a bit older. I figure this is it. I’m running towards them and I’m thinking, “this is it, I can do it – I’m going to get my $50 back!” As I pass them I turn around and say hello to both of them and smile. The one with the nice backside seems fairly cute from the brief glance I got of her. And it looks like she’s walking with her mom. They seem a little startled and reply with a rather meek hello.

I continue running until I’m about 20 feet ahead of them and then I just stop and decide to go for it. I turn around and start walking towards them. When I get to talking distance I just say to both of them:

“Hi, I’m sorry to bother to you, but I saw you walking here (looking at the attractive one) and I just had to stop and say hi.”
“Um…. hi, ” the daughter says to me.

They have that deer-caught-in-head-lights look. I’m actually not that nervous – I just want to have fun, so I say something ridiculous to the mom like,

“I was running and when I saw her (glancing at her daughter) I just had to stop. You understand how it is.”

The mother just looks at me like I just dropped off the moon and says “Uh huh.”

But as weird as this might seem to you, I have a feeling they were flattered. I got a better look at the daughter and she turned out to be not as attractive as I initially thought – maybe a 6. But I figured it’s worth the practice. So I start walking with The Deer in the Headlights and the Deer’s mom as I try and continue the conversation.

“So, you guys live around here?”

“Umm… yeah, close by, ” the daughter replies in a guarded way. I can see this is going to be an uphill battle – I’ve caught them totally off guard.

After a few more exchanges like this I decide to cut my losses. The girl’s not that attractive anyway and she seems to be very closed off to interacting.
I just get really turned off with women that act this way – it sends me the signal that they’re no fun. I’m not one of those guys that makes it his mission to try and get a girl out of her shell – too time consuming and not worth it most of the time.

So after about a minute of walking with The Deer in the Headlights and her Mom I excuse myself by saying, “Well, it was nice to talk to you. Have a good day.”

I start my run again, and I’m feeling pretty happy and relaxed for approaching her. I even have this smile on my face and a minute later I pass by a group of 4 boys. They’re all about 10 and are walking on the path in the same direction as I’m running. I just say a friendly “Hi, guys” to them and after I run past them I hear all this talking and suddenly feet stomping behind me. I turn around and all four boys have started running behind me!

Two of the boys drop out after a few seconds while the remaining two continue running. I felt like Forrest Gump when he was running across the country and there were all these people that joined him on his run. I felt alive, free, liberated from my fears and I just didn’t care what people thought.

Feelings like this aren’t permanent, though. Close to my building, I ran by a gas station and thought I spotted a hottie filling up her car. I hesitated and didn’t follow through – I just kept running while I glanced at her in regret. She was totally focused on filling up her car and had no idea that I noticed her – so it would have been another Deer-Caught-In-Headlight approach. I guess I felt I met enough deer for one day.

It would have been nice to have approached two women in on one run again. I think if I was closer to my due date of my approaching women challenge I would have gone for it. I’m sure one day soon approaches like that won’t be a problem – the same way I just couldn’t stop and talk to a woman while running only a month ago.

Things I Learned

• Having some extra motivation really helped me get over the last remnants of hesitation. If I hadn’t set out the approaching women challenge for myself, I could have easily rationalized to myself that the woman wasn’t that attractive or that she didn’t give me any indication she was friendly or interested. But I feel at this point I still need to push myself to get out there and approach more women. I think eventually, once I become very good at it, I won’t have to prove things like this anymore and can be more choosy who I approach.
• I specifically wanted to try being direct but in a genuine and fun way. I know this isn’t the indirect approach that I thought worked better in the past but I think it’s too hard being indirect all the time. I mean, what was I going to do: say “hi, can you tell me where there’s a restaurant close to here?” We’re on a path in the park, I’m passing them by from behind, I see she has a nice backside and when I turn around to say hello notice she’s decently attractive. That’s it. I just find it makes me more nervous figuring out what indirect approach to take rather than just being direct and conveying the messages: you’re attractive, I’m interested in talking with you, and this could be fun. Granted, I didn’t get the desired reaction, but I think I can improve my delivery and approach.
• I felt more motivated to complete my challenge, which made me feel more confident and relaxed. The last time I went running I didn’t stop to say hi to the hottie with the friend because I didn’t get any indicators of interest from her. Well tonight I didn’t get any either – the girl didn’t say hello back and she was walking with her mom. Yet I didn’t care as much as I did on my last run – maybe because the girl last night wasn’t as attractive as the woman from my last run. But I also think it’s because I’m learning to care less about what women think of me and to feel good expressing myself.

My main issue with her is that she’s a constant talker. I wouldn’t necessarily mind – my friend Yvonne also tends to talk a lot but it’s different with her. Anna just seemed to talk and talk and talk only about herself. She never asked me any questions about my life or my interests. I felt like I had to jump in and tell her about myself in the short gaps of silence that she would take in between her non-stop talking.

Here’s a tip for you women out there – ask the guy questions, too. I happen to think I’m a pretty good conversationalist and I take an active interest in the people I’m hanging out with. But I expect SOME reciprocal interest from other people. This wasn’t the case with her. Maybe she was too nervous to ask me anything or didn’t know what to ask, but I just found it boring to sit there for 2 hours (the length of our date) and listen to her go on and on about her life and her interests without feeling like she cared about mine.

I have to say – I’m a sucker for women that ask me about my interests, my passions, my beliefs, etc. I feel I do that with women I go out with but I don’t often get it in return.

My second issue is that I’m just not that attracted to her. I sensed it when we first met at the bookstore but I thought I shouldn’t judge her so quickly. But after going out with her twice now, I think it’s an issue for me. If you must know the details, she’s overweight. Not like Angela but enough that I notice. She’s got thicker arms than I’m used to seeing on a woman and her body is just not the type that really turns me on.

During our date I noticed a really hot woman come in to the restaurant and sit at a table less than 10 feet away from me and in my line of sight. She was there by herself and no one showed up to join her while she had an entire meal. She was obviously lonely since she checked her cell phone a few times during her meal and I couldn’t help but feel this surge of confidence that if I weren’t sitting with Anna (and getting kind of bored) I’d totally approach her. I was most fascinated by the fact that I didn’t experience any approach anxiety. I just thought – hey, I made this challenge for myself, I’m currently out $50, I’ve been practicing talking to women already, I’m feeling attractive and confident and this could be a lot of fun! I think that was my favorite part of the evening – fantasizing how I would approach this hot woman.

My third issue with her is that she’s a judgmental condescending perfectionist. For example, she’s a big connoisseur of food and takes a lot of pride in her cooking abilities. That’s great – I love it when people have interests they’re passionate about. But she seemed to cast judgement on me when I recounted how I cooked a dish. As I’m telling her my story she got this condescending look that told me she thought I was doing it all wrong. And the way she spoke to me as I was telling her my story – like she was trying to suppress herself from saying, “You’re doing it all wrong”. Man, that’s a big turn off.

She also told me she’s not a very patient person in the kitchen with others and told me a story of how a friend that didn’t know how to cook was helping her out but she lost all patience with him when she realized he didn’t know the difference between dicing and slicing. She ended up making the entire dish herself while he passively watched from the sides. I just thought, “You’re someone that prefers to be right all the time versus seeing opportunities to connect and share yourself with others.”

Now, I happen to be into running and if someone totally new has questions or is doing something I disagree with, I would look at it as an opportunity to have a meaningful conversation where I share with them my experiences and ask them questions to understand them better. I wouldn’t act like they’re a moron and I’m this expert.

So after a couple hours of this, I thought I should cut my losses and suggest that we get going. I paid the bill just like I did the first time we went out. She offered to contribute, but in that half-hearted way that made me think it was more of a polite gesture than a real offer. I just shrugged and said it’s OK. Maybe I should’ve split it with her after all – not like I was planning on seeing her again and this wasn’t our first date. Then again, we just had a couple of drinks so it wasn’t like we had this full meal. I think taking a woman out to dinner at a restaurant is total overkill for a first, second, or even a third date. Too much pressure, too expensive (if you plan on dating multiple women) and it doesn’t contribute to the fun factor.

As we were walking out of the bar, I noticed this attractive woman talking with a guy by the window. As I was walking towards the exit, the woman and I exchanged a glance. I felt she was checking me out and I held her glance – whereas in the past I would have been likely to turn away.

I offered to give Anna a lift to her place but she preferred to walk. I ended the date by hugging her and telling her I had a nice time (that’s the nice guy side of me not wanting to hurt her feelings). She didn’t insist on a date for our next date, so maybe she felt the spark wasn’t there, too. She said, “So we’ll call each other to go out again.” Maybe she was going through the motions, too. I kind of kicked myself for not being more upfront and honest with her right there. Now, I’ll have to make “the phone call” to tell her what I could have said last night. I think I just didn’t want to hurt her feelings, in case she thought we had this great time. After all, she got to talk a lot and express herself. I guess I didn’t want to splash cold water on her face and tell her that I’m just not into her right at the end of our date. I wanted her to think that I spent some time contemplating it before making my decision – that’s the nice guy side of me that’s trying to please women and not hurt their feelings coming out.

I think it would be OK to stop seeing Anna – if the spark isn’t there there’s no point acting desperate and continue seeing her “just in case” things improve or I won’t manage to find someone. I can already feel how knowing I can easily go out and meet more women keeps me from compromising my standards. I can’t wait to complete my approaching women challenge! It’s working already!

Rules for The Approaching Women Challenge

• Approach a total of 50 women before June 18, 2007. The pick up approaches that I’ve already done count towards the goal. That means I’m up to 21 already. Interestingly enough, I’d actually be at a higher number if I set these rules up previously – like my very first post where I picked up a woman on the subway. So this means I will approach 29 more women before the due date.
• I’ve given a close friend of mine $50. If I reach my goal by my due date, he gives me back the money and if I don’t, he keeps it. Simple as that. I wanted something more concrete to keep me focused on my goal. Even though I might know in my head why I’m doing all of this (so I can improve my life and so forth) there’s nothing like the potential loss of money to give me that extra push and prevent me from making excuses.
• Talk to each woman for at least one minute – that way I can’t count saying “Hi” or asking, “What’s the time?” as an approach. At the same time I don’t want to have the pressure of asking each woman out that I approach – I’ve already made that insight before and it’s served me well. So after one minute of talking, I can decide if I should continue talking to her or move on. Following my previous insight, this means I do not have to ask out every woman I talk to.
• The outcome is not important – it doesn’t matter if she says yes, no, completely ignores me, gives me a fake number or I decide not to ask her out. The main point is to make it no big deal to approach women I’m interested in. Period. In public, at parties, wherever.
• Talking to a group of women counts as one approach. So if I end up talking to a group of three women at a bookstore, it counts as one approach.
• If the woman cuts off the conversation before one minute, it still counts as an approach. So in the (highly unlikely ) event where she flat out says, “Get lost!” or “I can’t talk right now.” I should still get credit for approaching her.
• Talking to female staff (waitresses, store clerks, etc.) only counts as a pick up approach if I ask them out. It’s too easy to talk to women that are naturally more open to talking (e.g. when I’m a potential customer at a store). So if I happen to like a waitress and decide to ask her out, then it counts as an approach.
• Talking to women at social events (parties, networking meetings) doesn’t count as a pick up approach, unless I ask her out. That way I can’t count talking to a slew of women at a party as approaches.
• The woman must be reasonably attractive and close to my age – that way I can’t count talking with little old ladies as an approach. She doesn’t have to be hot but someone I could conceivably go out with.
• If I start dating someone exclusively before I reach my goal, then I get the money back. That way, I won’t feel pressured to continue talking to women after I start seriously dating someone. (Who knows, I might end up amending this rule since I don’t have to ask women out, just talk to them.)

Improving my ability to meet women is more important than dating or even having sex right now – besides not being attracted to Angela, I also felt that continuing being friends with benefits with her was going for the easy sex and not improving my ability to meet more women. It was a short-term win but a long-term loss. Don’t get me wrong – if I end up dating and sleeping with women that I’m pursuing right now, I’m not going to be a dumb ass and say no. But I want to make it clear that that’s not my goal – it’s not to sleep with more women or even go out with more women. It’s really about improving my ability to meet more women. I know the dating and sex will naturally follow if I improve this one area.

Ultimately, though, it’s about meeting the one woman that I can settle down with.

So wish me luck and let me know what you guys think – good or bad. I’d love to hear from you.

I have no problem coming up to an elderly man or woman, saying hello and start talking to them. I can also do the same with kids – I can join in the game they’re playing or say hello to them in an open, friendly way and not worry about how they respond back – in fact, I think I’m pretty good with kids.

So why do I get nervous doing the same thing with women closer to my age? I guess I feel they’ll judge me – that I’m weird or a creep. After all, who goes around talking to strangers on a regular basis? And yet, I don’t have that thought when I start talking to an elderly person – I think that they’ll think that I’m nice and friendly. Maybe because I’m assuming that they feel lonely so someone talking to them is a treat. With kids, I just assume that they love to play and be silly so I can jump right in and play and be silly with them.

But with women that I see out in public, I feel like I’ll just be one of many people vying for their attention. Or she’ll think I’m weird or she’ll get annoyed. The mental blocks that keep me from approaching women are rooted in wanting to be liked. After all, I want them to like me – to think I’m dashing, handsome, funny, intelligent, etc. But it’s hard to have both thoughts at the same time – “I hope she’ll like me.” and “Let’s have fun talking to this woman.”

The problem is: I care too much of what women will think of me.

If I didn’t give a rat’s ass what a woman will think of me, I’d start way more conversations with women than I’ve been doing. Like the woman I ran by and didn’t stop to talk to last time I went running – I cared too much what she would think of me. But with Amber, the woman I picked up at the end of a run, when I just wanted to have some fun, I didn’t care what she thought of me (because I had already picked up Jennifer earlier on in the run).

Now I’m not saying dress like a slob, don’t shave, and look like a pig. That’s more about self-respect than seeking to please others. But I do think that I spend too much time thinking unproductive thoughts like, “What am I going to say to her?”, “What if she thinks I’m weird?”, “What if she doesn’t like me?”, “What if all the other people around her think I’m weird?”

When I was out a couple of days ago with my parents at that Starbucks where I didn’t talk to the hottie that was studying by herself, I saw another interesting scene. A guy came into the store and ordered a drink. This guy was in his early to mid 40s and he had this air of arrogance about him. Just the way he was dressed and the way he walked and carried himself, I felt like this guy had a big ego. A few minutes later this hot looking woman walks into the coffee shop and it turns out they’re together. They happened to be sitting in my line of sight so I watched as the two of them talked and then the woman proceeded to sit on the guy’s lap as he rubbed her back, under her shirt. It made me wonder about the nature of attraction and how this hot woman ended up with someone who I thought was an arrogant prick. I think it had something to do with the guy appearing confident and sure of himself to the woman. I wondered if that guy cared what other women thought of him. I think not.

It’s a weird paradox that I’ve mentioned many times before – the more a guy cares what women will think of him, the less women will think of him. And the more a guy expresses himself without caring what women will think, the more women will find him attractive. Deep down, I know there’s a guy inside me that’s got so much life, pizzazz, and excitement. Why am I afraid to show that to the women I meet? If I absolutely didn’t care what women will think of my pick up approaches, I’d get way more creative, experiment with different approaches and just live life more fully.

After sharing my thoughts with you, I feel empowered and ready to keep growing and exploring. I’m thinking of setting some new goals in this area of my life. I’ll be posting more about it soon.

Yesterday, I was out on my run on a beautiful Sunday morning. I ran through the park and said “hello” and “good morning” to most people I passed. I wasn’t looking to pick anybody up and I just wanted to enjoy my run. On the way home, when I was already out of the park, I spot a couple of hotties walking on the sidewalk ahead of me. They’re walking away from me so they can’t see me approaching.

There’s a part of me that thinks too much about these kinds of situations. One part of me thinks, “Hey, you have nothing to prove – you picked up Jennifer and Amber a couple of days ago, you’re dating Anna and Eve, and there are a couple of other women that my friends want to set me up with – so chill out.”

The other part of me thinks, “Here’s another perfect opportunity to practice talking to a woman in public. I can just talk to her and not ask her out. Besides, I don’t want to fall back to old habits of making excuses on why I can’t strike up a conversation with a woman I find attractive.”

Then there’s a third part of me that thinks, “OK, what am I – some kind of wannabe pick up addict? Am I going to practice until I can talk to every single attractive woman I see while I’m out? Am I going to stop my car as I’m driving because I spotted a hot woman walking on the street? Am I going to stop talking with my friends while I’m out because I spotted someone I want to talk to? I mean – how far is this going to go?”

As I’m passing them by I decide to just say hello. It’s a little awkward because there’s another group of people just ahead of the 2 women so it’s a little crowded and we’re also close to a major street so there’s a lot of noise from there. I say hello to them as I pass by and I see that one of the two women is just gorgeous. Up to know I only had a view of their backsides but now it’s confirmed – one of them is definitely a hottie.

But it feels really weird to just stop right there as I’m passing them by from behind, so I continue running until I reach the major street ahead. I then decide to run back towards the 2 women so I can stop and talk to them. I start running back and within a few seconds I have my opportunity so I do…. absolutely nothing! I run by them, again, and don’t even say a word. Man, that sucked!

I always feel it’s way better to get totally rejected than to do nothing in situations like this. At least if I got rejected, I would have felt invigorated and energized just for having the balls to start talking to them in the first place. But instead, I felt down for not going beyond saying hello to them.

Fast forward to later in the day. I was out with my family to celebrate Mother’s Day and we all stop at a Starbucks coffee shop. As we’re ordering our drinks, I spot a really attractive woman who’s also waiting for her drink. We exchange a glance and I thought I sensed some curiosity from her. She then proceeds to sit at a table and read over some books – all by herself! This would be a perfect opportunity to approach her, but I’m with my parents and sister. I’ve already tried to pick up a waitress when I was out with them, but this situation is a little different. I hesitate and decide to let this one pass. Damn it. There was even an opportunity when I had to look for some extra chairs for our table so I asked a couple of patrons if they minded if I took their unused chairs. But I didn’t use that as opportunity to ask the hottie that was sitting by herself and who exchanged a glance with me. Damn it!

When I’m feeling down for not taking action, I rely on my daily habits to keep me grounded. I’ve been going out every day on my daily morning pick up practice and today was no different. I ended up saying hello to about 10 people and I even skipped rope with some kids! There were a couple of kids on the sidewalk with their grandmother – the grandmother and one of the kids would turn the rope while the second kid would be skipping the rope. I just joined them and said, “Hey, do you mind if I skip with you guys?” So they let me have a go at it and I felt great afterwards! I’ve said it before and I’ll say it again – picking up women is about being more social with people in general and having fun.

I feel that at this point in my dating life, I should continue taking chances. I think eventually, I’ll come to a point when I won’t feel like I’m missing out on an opportunity if I spot a hot woman and don’t approach her. I remember feeling that way with my last girlfriend who I was very attracted to so I’m sure it can happen again.

So after I managed to pick up Jennifer, I continued running back home. I didn’t feel like I had to prove anything – I was just feeling happy, serene, relaxed. Ironically, that’s when I find I do better with picking up women. The less desperate you are for any one woman, the more attractive you are to her.

I stopped running about 500 yards before reaching my building and started walking. As I’m getting ready to turn into the driveway to my building I thought I noticed an attractive woman walking towards me. I didn’t pay her any attention, though, and just continued walking towards the building entrance. But then I hear this “tap, tap, tap” behind me. OK, now I’m curious, so I turn around and it’s the woman. So she turned into my building’s driveway, too. I’m honestly not thinking I’m going to pick her up and I just want to have some fun by joking around and talking to her.

As I’m turned around I say something like “Tap, tap, tap. That’s all I hear behind me so I had to turn around and look.” She just smiles warmly and says, “Yeah, it’s my shoes.” I say, “Are you a tap dancer or something?” She just laughs and says no and I ask her if she’s coming back from work. She replies that she is coming back from work but then tells me a bit more about the nature of her job which makes me want to ask her more questions. So we continue this spontaneous conversation all the way to the elevator. Normally, I would do my stretches in the exercise room on the first floor but since I’m talking with this attractive woman, I figure I’ll just go in the elevator with her and continue the conversation and then come back to do my stretches.

Turns out she doesn’t live in the building and is house sitting for a friend for a month. Perfect. Last thing I need is to start dating more of my neighbors and get some kind of reputation in my building. I’ve already gone out with one hot neighbor and there’s another neighbor that I started flirting with – that’s quite enough for me.

We continue talking and it’s all very friendly and casual. I was planning to ask her out in the elevator but I run into a problem – another neighbor walks into the elevator (older lady walking her dog) just as the two of us are about to go up. I thought it would seem awkward to ask her out in front of this other lady. The cute girl is only going to the second floor and as she gets out of the elevator I think for a split second to come out of the elevator and just ask her out in the hall, after the elevator closes. But I thought that would be too weird so I just smile and say good-bye to her as she’s leaving. Damn it.

I go back to the exercise room to do my stretches and then I get this crazy idea – what if I tried knocking on her door directly so I could ask her out today instead of waiting till we might bump into each other again. Yes! I feel this rush of excitement – like I’m some kind detective who’s going to look for the right door to knock on.

I quickly finish up my stretches and head up the stairs to the second floor. I knew she got off on the 2nd floor but I’m not sure which unit she went into. However, I remember which way she turned as she left the elevator so I can narrow down the choices to one half of the second floor. Only about 8 or so units on that side so I figure I have a decent shot if I try a few. I go to one end and start knocking on the doors. Sometimes I get no answer, which is nice since it prevents an awkward interaction. But more often than not I get a “who’s there?” from behind the door and the only half-decent response I can think of is, “It’s your neighbor”. Sometimes they open the door and sometimes they just ask “What do you need?” and I have to reply with a really awkward question, “Were you just in the elevator?” I tried about 5 or 6 units and it’s getting kind of embarrassing and I’m really close to just giving up. I decide to knock on one last unit and if it’s not hers to just forget it and throw in the towel. A young woman answers the door but it’s not the one I talked to. I just say “Hi, were you in the elevator just now?” and she replies that she wasn’t. Damn it. I just say, “OK, thanks.” and start walking away.

But as I’m walking away, I hear the sound of another woman and as I turn around the girl I talked to in the elevator comes out into the hallway with this quizzical look on her face. Yes! Found her! I go back to her and just say something like, “Hi, I didn’t get a chance to talk more to you in the elevator so I wanted to come back and ask you… if you wanted to hang out sometime.” The original woman that opened the door is standing there and witnessing all of this take place and eventually excuses herself to go inside so we can have a moment by ourselves. After her friend goes back inside, she asks me in this amazed tone, “How did you know where I live?” After all, she never told me her unit. I forget what I said but I don’t think I recounted my whole adventure to find her. I’m sensing there’s a curious interest from her. She was friendly downstairs when we first started talking and I think she was pleasantly surprised by my appearance. She says she’d be up for getting together and we exchange a few more words. She tells me her name, Amber, and we spend about a minute talking further. But before we can talk further there’s some sound from the kitchen and she tells me that she can’t talk right now because of her dinner cooking duties. I tell her I have to go now, as well, but ask her what’s the best way to get in touch with her. She scribbles her email address on a scrap of paper and hands it to me and we say good-bye.

So when I got home from my run, I had 2 women’s numbers (well, 1 email and 1 number). I felt happy, relaxed and alive! This has never happened to me before. It’s like I’m feeling the world open up with opportunities.

Things I Learned

• Not caring about the outcome really helped me be more relaxed. I had already picked up Jennifer earlier on my run and I wasn’t out to prove anything. I just wanted to start a conversation with Amber and had no intention of picking her up. I’ve said this before and I’ll say it again – women seem to respond better when I don’t care how they respond. The less I care whether they say yes or no when I ask them out, the more they seem to say yes (or want to say yes). It’s one of those weird paradoxes in life.
• I should have come out of the elevator when Amber got to her floor. I would have saved myself the trouble of finding her unit and I could have asked her out sooner. I cared too much about it looking weird but then I ended up knocking on a bunch of other people’s doors anyway, which wasn’t any less weird.
• Picking up women is really just being more social and friendly with people in general. It’s better to focus on being friendlier with everyone and women will pick up on that. I think my daily morning pick up practice and saying hello to people when I run has helped me be more social in general.

I went running yesterday in the park. It was an early Friday evening, the sun was shining and I was just trying to relax and get some exercise. I was a little nervous about picking someone up – I don’t want to put too much pressure on myself for having to try and pick someone up every time I go running, but at the same time I don’t want to get lazy and not take any chances. So I decided I was going to be friendly and say hello to everyone I passed and if I happened to pass a woman I wanted to talk to, I’d just let my sub-conscious take over and see what happens.

As I was saying hi to people I passed by I could feel myself loosening up socially and feeling like I can actually approach a woman – I feel these warm ups are really important, which is why I’m continuing to do my daily morning pick up practice.

About a third of the way into my run, I see a couple of attractive women walking from another path and getting ready to merge with my path. But since they’re not passing directly in front of me, I feel too awkward to just stop and start talking to them. I rationalize to myself that when I turn around, I’ll run into them again and then I’ll start talking to them.

I continue running and a few minutes later I see 2 women and a guy walking. Both women are quite attractive. All 3 are wearing business attire. One of the women has a sexy business skirt with a red dress shirt while the other is wearing quite flattering business pants and also a red shirt. This is kind of a strange site in a park. I don’t feel confident enough to just stop and start talking to them but I manage to say, “Isn’t this kind of formal for the park?” as I’m running by them. Both women laugh and one of them says “We’re taking a walk after work.” I smile back at them and continue running. I reach my halfway point and turn around.

I’m getting ready to see the 2 women walking together that I totally passed by without saying a word. But they’re nowhere to be found. I’m feeling a little down but somewhat relieved that I didn’t have to take another chance with a new woman (old fears die hard). And then I spot the 2 women and 1 guy walking up ahead! I’m running towards them and I start thinking: The women seemed friendly and open – let’s just see what happens.

As I run up beside them I just stop running and start walking with them. I open with something like “Hi! So I just had to find out more about you guys. It’s not everyday you see people dressed this way in the park.” The women and guy all smile and respond warmly and the 4 of us continue walking together. I make some joke about how the 2 women are both wearing red and if they planned that. They both laugh and say how they didn’t mean to wear the same color to work that day and I just joke that I thought women have this 6th sense about fashion and always wearing something unique from other women, so maybe their sensors are broken or something. They laugh and I can feel their friendliness and openness. Turns out they all work at the same company and they regularly come to the park for walks. They ask me how often I run in the park and at what time and then one of them says that they should come walking in the park at a time that coincides with me running there.

All 3 of them have a slight accent and I recognize it as my native language, so I ask if they’re from that country and they say they are. I tell them I am, too, but they’re surprised to hear that because I don’t have an accent. I introduce myself and they tell me their names – Jennifer, Tanya and Steve. Both Jennifer and Tanya are very attractive but I notice that Jennifer is friendlier while Tanya is more quiet. Steve also seems friendly and he starts asking me questions about what I do and it turns out we have stuff in common with what he’s working on. I didn’t want this to become a shop talk session so after a minute of shop talk with Steve I bring the focus back on Jennifer and Tanya by making a joke about how they’re the big techies in their company (which they didn’t strike me that they were). They both laugh and we start talking about their background and education.

We must have walked together for about 10 minutes and eventually come to a fork in the road – they’re going one way while I’m going the other. Steve hands out his business card and gives it to me because he thinks we could possibly work together in the future and to stay in touch. I tell them that it was nice meeting them and that it would be great to run into them in the park again.

And then I decide to go for it.

I say to Jennifer: “Listen, I don’t know if I’ll run into you here again, so instead of waiting for that possible chance, I figured I’d just ask you right now if you’d like to go out sometime.” Jennifer smiles and giggles and looks at Tanya and Steve, who are both smiling and giggling. I’m just standing there with a smile on my face, too, knowing that I’ve probably given them something to talk about after we’ll part ways in a few minutes. I add, “I’m not really sure what the dynamics of all of you are – I don’t know if Steve is with you but I thought I’d ask anyway.” Then Steve tells me that he’s not with Jennifer and that he’s Tanya’s brother. Great! So now Steve is actually helping me out by implying that Jennifer is single and available.

Jennifer replies with “Why don’t you call my company and we’ll take it from there. You have Steve’s business card so call and ask for me.” I say “Great, I’ll do that.” and wish them a great weekend as I tuck away Steve’s business card into my running pouch.

I continue running for home and say hi to almost everyone I pass. What a great start to the weekend! But I didn’t know that I was going to pick up someone else that day, too. I’ll post that tomorrow.

Things I Learned

• Ask out the one woman I’m interested in and not both at the same time. Unlike my last pick up attempt, where I asked out both women at the same time, this time I asked out Jennifer explicitly so it was clear I was interested only in her.
• Talk to everyone in the group. I’ve been doing this already, but it’s still worth mentioning. I talked with all 3 people in the group so I came off as friendly instead of like some stalker dude who was only focusing on the one woman and ignoring everyone else.
• Don’t get sidetracked into shop talking with the guy. I could have easily continued talking shop with Steve, but that would have ruined my chances of building a connection with Jennifer. So I made sure to change the subject quickly and refocus on including the 2 women in our conversation.
• Smile and stay upbeat as I’m asking her out. I think it shows gutsiness and that I’m going after her without any excuses – but in a respectful way. I like how I feel afterwards and I think women appreciate it, too. I think women like to be asked out by confident, gutsy guys.

I was fairly laid back and relaxed the whole night. I wasn’t trying to impress her but more just get to know her and listen to her. I found this worked out really well for me. She’s quite the talker so I’d say the conversation was about 70% her talking. I didn’t mind because I think I’m a good listener but I kind of wondered after a while if she was going to ask me anything about myself. I think some women don’t ask questions to guys because they expect the guy to just start talking about himself spontaneously.

One of the things she reminded me about the night we met, was that after about a minute of starting our conversation, the store clerk directed her to another section of the store for a book she was looking for. She made it a point to come back to where I was after that. Normally, she would have just left the bookstore but there was something compelling her to come back to me and continue our conversation. And this was after only a couple of minutes of us talking. Wow. I didn’t even remember that and it was flattering to hear it.

We flirted a little bit throughout the evening. I told her that she looked good. I think she looked better than when I first met her. She told me that I looked good, too. She made some references of how she’ll have to show me such and such in the future, implying that she wanted to see me again. We had a mini foreign language lesson where I taught her some words in my mother tongue and she would repeat it and we’d laugh together.

When we finally decided to leave, she asked if I want her to pay for the bill, which I thought was a little weird. I mean, usually women ask if they can contribute to the bill, but she asked to pay for the whole thing. I just shrugged it off and said I’d pay for it, which I did. She then walked me to my car. I thought that was different since I thought I’d walk her to her building. But I’m thinking it’s a trust issue, so she doesn’t want me to know where she lives.

At my car, I felt pretty confident going for the kiss – I just figured we had a great evening of non-stop talking and I thought we really connected. I pulled the sides of her jacket into me so she would come up close to my face so I could kiss her. While I was doing that, she said she doesn’t kiss on the first date and I didn’t push it any further. That started another discussion because I wasn’t sure if this was our first or second date, because we did spend a few hours talking to each other the first time we met at the bookstore. She thought about it, too, but decided that tonight was our first date.

She then asked me, “So when are we going to get together again?” In some ways, she was like the guy tonight – she wanted to pay the bill, she walked me to my car, she wanted to set a day for the next date. So we settled on a date for next week. I gave her a warm and big hug good bye and drove home. Oh, and she asked me to call her when I got home to tell her I made it home OK – is this girl falling for me?

Things I Learned

• Having something to do while I waited for her to show up made me more relaxed. She was just a few minutes late but I didn’t care because I had brought my pen and notepad so I could do some planning while waiting for her. That way, I wouldn’t be sitting around getting all resentful if she was late and I’d be more friendly and open when she would arrive.
• I set the tone of the date by greeting her warmly and giving her a hug when I first saw her. It had been almost 2 weeks since we met each other and I wanted to show her that I still felt connected to her. I think she was nervous at first and by me reaching out to her and making an effort to make her feel at ease put her in a more relaxed mood at the start of our date.
• Talking about romantic topics made our connection stronger. After we had talked about some neutral topics, I asked her, “Have you ever been in love before?” I really wanted to know her answer and that would also make the mood of the evening more romantic. That got us talking about many related issues – relationships, love, trust, etc. I wanted to get away from the standard “resume” questions people usually talk about on the first date – Where do you live? Where do you work? After all, we’re all looking for a connection so why not talk about topics that are close to our hearts.

I called her up a couple of nights ago with the intention of saying I had met someone. I wasn’t totally sure about this approach, but I thought it would be the best and easiest explanation. I didn’t want to tell her the real truth because that would be unnecessarily cruel. On the other hand, I know that she wanted us to have a relationship so I felt that telling her I had met someone that I wanted to get more serious with would also make her feel very rejected – since I’d be saying I wanted to have a relationship with someone else and not her.

Thankfully, I got her voicemail – so I left her a message (in a friendly sounding tone) and asked her to call me back. She called me back later that evening and by then I had enough time to make up my mind of what I was going to tell her when she would ask the inevitable “why?” question.

I told her that I really enjoy our times together and that I still wanted to continue doing that – but that we should stop having our sleepovers.

She asked me why (of course) and I just said I didn’t feel comfortable with our arrangement anymore. I told her that these types of arrangements usually don’t last long since it’s hard to sustain it. She asked me if I’ve been in this type of situation before. I told her I have but not often. I didn’t go into details, since that would have been pointless. I tried to sound caring but firm – I cared about her feelings but at the same time, I knew I wasn’t happy continuing it.

She said she was disappointed but I could tell she wasn’t devastated. I thought I took the right approach. She even told me to take a deep breath and relax, after sensing that I was somewhat tense telling her this. That made me feel better since it showed that she wasn’t as hurt as I feared.

I wasn’t in a particularly pick up mood, to be honest. I’m still not totally comfortable trying to pick up women while running – it still seems a little foreign to me. I was determined, though, to practice being social and friendly – I made it a point to say hello to almost everyone I would pass. This time, though, I would smile warmly and say hi in a more open and friendly way. So it wasn’t like a “drive by” hi that I say at the last second as I’m passing them by. Instead, I would smile and say hello to them when I was a good 20 feet away. That way there would be time to see them say hi back and smile. I’m even saying hello now to people that I pass by from behind, which I didn’t use to do before. As I pass them by, I look back, smile and say hello. Usually, they smile and say hello. It’s these little things that really help me be more social when I want to talk to hot women.

About half way into my run, I see a couple of attractive (mid twenties) women running towards me! I don’t see this very often so I wonder if this is a sign from above. But I wasn’t feeling confident enough to stop and start talking to them, so I only manage to say hello and smile at them as we pass each other. I’m kicking myself inside for not taking any further action. The fear of rejection or disapproval from woman is a powerful force for many guys (me included) that I’m really trying to tame and keep in its place.

I continue running towards my halfway point and keep saying hello to people I pass. I get to my halfway point, turn around and start running back. I start thinking of ways I could incorporate practicing picking up women while running without having to actually do it each time. Kind of like my daily morning pick up practice where I say hi to people in my neighborhood. I’m almost out of the park by now and am ready to start running for home, when I see the same two women running towards me again! So it looks like they turned around the same time as I did.

My thought pattern went something like this:
OK, this is it, this is it! This is a perfect opportunity. What have I got to lose – if they say no, I’ll just continue running for home and chalk it up to another learning experience. One of them is really hot and this could be fun!

So as we get closer to each other I say hello again. As soon as we pass each other, I turn around and in a matter-of-fact tone say something like “Hey, you guys mind if I run with you?” They look at each other not knowing what to say, so while they’re caught in this pause I just run up to them and say “I know it might seem weird and all, but why don’t we try it and if after a minute it’s not working I’ll be on my way.” They shrug in a “why not” kind of way and we start running together.

I’m pretty upbeat and friendly, asking them questions about their running, if they’ve been in this park before and what they do. Turns out they’re from a different part of the city but not that far away. After a few minutes of talking, I introduce myself and they tell me their names – Heather and Nina. They both seem nice but I’m definitely more interested in Heather than Nina. She’s got this sexiness to her but she also seems friendly and open. As we’re talking, Heather even asks me a few questions about my running and some of my running gear. I take that as a good sign since she wouldn’t be asking me things about myself if there was no interest. The whole vibe is pretty friendly and casual. Turns out Heather is a fitness trainer (yes!) and is teaching Nina how to run. They do a combination of running and walking so we end up walking for most of the time, which is OK with me since I’ve already done most of my run. Heather tells me a little of what she does, too, and how she works with kids. I make a few light-hearted jokes about one of her stories and we all laugh, which breaks up the tension. We spend about 10-15 minutes just walking and talking – there’s a connection there but it’s still hard to say if the connection will grow deeper.

We also have some gaps in our conversation, too, but I wasn’t as concerned about it as I would be in the past. In the past, I’d be desperately trying to keep the conversation going all the time. Nowadays, I’m OK with having a few gaps in – it’s normal and nothing to get hung up about.

I eventually tell them that I should be getting back and that it was very nice to meet up with them. They tell me the same and I’m debating whether to ask Heather out. What the hell, I go for it…

As we’re saying our good-bye’s I say, “Listen, I don’t usually do this kind of thing, but would you guys like to go out sometime?” I didn’t really ask Heather out, I kind of asked both of them out at the same time. There’s a pause, they look at each other again, and Heather says “Why don’t we run into you here again and we’ll take it from there?” I say, “Yeah, right, like I’m going to see you guys here again – you’re not from this area.” I just look at them, without saying a word, with a “why not?!” expression on my face. After a few more seconds, Heather says, “I have a boyfriend.” Then Nina says “And I’m engaged.” So I just say, “OK, no problem.” It got a little awkward for a bit there but I try to ease the tension by wishing them luck in their training.

I got the sense that I was close to Heather saying yes. A thought that came to me afterwards was that I should have made some kind of an arrangement to meet up again at the park. That way, she’d feel safe and wouldn’t have to give out her number or make any commitment, while at the same time keeping an opportunity open. I’m not sure I bought the “I have a boyfriend” excuse because why didn’t she mention it after the first time I asked her out? I think she just wasn’t ready to give me her number – but I think there was an interest there.

I ran back home, feeling great about what happened. I’ve never started a conversation with two women while running and actually had it continue for that length of time (10-15 minutes). I kept saying hello to people for the rest of the run home and I felt good about having put myself out there. I’ve said it before but I need to keep reminding myself – it’s more important that I tried picking up than whether I picked her up or not.

Things I Learned

• At the heart of approach anxiety and fear of rejection is the fear that someone won’t approve of us or think we’re strange or weird or stupid. The same fear that kept me from not saying hi to people that looked like they were busy talking to other people, kept me from not approaching Heather and Nina the first time we ran past each other. I just thought it would be too weird – more precisely, I thought they would think that I was weird. By continuing to say hello to virtually everyone I passed, I conditioned myself to think it’s normal to start talking to people that I meet while I’m running. Picking up women starts in the mind, long before the first word is uttered.
• I spent time building a connection. It would have been nice to spend half an hour with them – and maybe I should have! But I felt that our conversation started to lag so I thought that would be a good time to excuse myself. In the future, it would be nice to see how long I can stretch the interaction. The longer we talk, the better my chances of her saying yes when I ask her out. I found this to be the case when I picked up Anna at the bookstore.
• I should have focused on asking out Heather, the woman I was interested in, instead of both of them. I wanted to be nice and extend the offer to both but I was really only interested in the more attractive one. Sure, it might seem less threatening if I ask them both out together, but I could have directed my gaze on the one I was interested in while asking her out.
• I liked that I didn’t walk away right after their initial resistance to me asking them out. I tried again by saying that we’re not likely to run into each other again and then just looked at them. Now, maybe that wasn’t the best way to go about it, but at least I didn’t give up as easily as before. This is something that I’ll develop as I practice more pick ups. I find that women tend to resist new interactions – maybe it’s a safety mechanism and/or social conditioning, but I think I can eventually get past that so they can see that I would be safe and fun to hang out with.
• I was fairly easy going throughout the interaction. I wasn’t that nervous, even though I started talking to a couple of women and one of them was quite attractive. This is great progress, since in the past I tended to get nervous when talking to hot women. There’s still a lot more work to be done here, but I can feel myself improving.
• I made sure to include both women in the conversation and not just the one I was interested in. I like this approach since it shows I’m a generally friendly person. If I was in a group of new people and there were guys there, I’d talk to them, too. I think too many guys only focus on the one woman they’re interested in and that can come off as too intense and unfriendly.

I hadn’t really planned on practicing any pick ups, especially with my parents around – but I found that that side of me just naturally came out – I wasn’t even trying. At first, there was another group of diners sitting at a table across from us – a family with 2 grown daughters and a son. It just so happened that they were in my view and I exchanged a couple of glances with one of the daughters.

Then there was our waitress – attractive, friendly and open (not cynical and just “going through the motions” like many waitresses do).

I’ve never tried picking someone up at a restaurant before and I found it a relatively easy experience. The waitress had to come by our table multiple times throughout the evening and those were great opportunities to exchange a few words and have these mini conversations and build a connection with her. She came by with a bottle of wine and my sister was the one who was supposed to approve it – so I asked the waitress if anyone had ever sent a bottle back which turned into this nice exchange between us. Or the time I came back from the bathroom and the waitress had asked me if I wanted to order coffee like everyone else had and I joked with her that that was a lot of peer pressure but that I was going to be different and order tea – and we had this little exchange and shared a couple of glances during that.

My family was apparently noticing my behavior and at one time my sister made a comment that I was embarrassing her, which I thought was strange. I was just talking with the waitress a bit more than most customers do but I wasn’t doing anything inappropriate. I don’t think my mom, dad or my sister’s boyfriend minded. I just think they were used to seeing me behave a certain way – since I wouldn’t normally flirt with waitresses and this was a bit of an eye opener for them. They don’t know anything about my pick up practice so this was their first glimpse into my new way of life.

I decided I was going to ask out our waitress somewhere towards the end of the dinner. It was one of those decisions that I didn’t hesitate on – I really wanted to do it – no doubt in my mind, no nervousness, just a determination to do it. I felt I had a connection with her and that I’d feel better for doing it.

So I had to wait for the right time – I didn’t want to do it in front of my family so I waited till we all started getting up from out table and I told them I’d go use the bathroom. My plan was to ask her out while they were waiting outside by the car. But then my mom said she needed to go to the bathroom, too. Damn! I didn’t want my mom seeing me ask out the waitress (not that that would have been a big deal). Everyone else waited at the front of the restaurant for us.

I went into the bathroom and quickly came out, thinking that I could do the deed while my mom was in the bathroom. But I couldn’t find her! So I asked one of the other waitresses to find her for me. She soon appeared and had this look like “Is everything OK?” Maybe she thought I was going to make a complaint or something.

I told her in a relaxed manner with a smile on my face, “Listen, I don’t usually do this, but you seem like a really genuine and nice person and I was wondering if we could go out sometime.” She smiled and said, “I think my boyfriend would have a problem with that.” I replied with, “Well, he’s a lucky guy.” and was ready to leave and then she added, “But if you come back we can have a drink at the bar.” I said, “Sure, that sounds nice” and went to join my family who were still waiting for my mom.

Things I Learned

• I felt really good about asking her out – I wanted to do it no matter what her response would be. I’ve noticed this many times before – the fact that I show my interest in a woman is more important than her response. This might evolve over time but I’m still feeling like I’m learning how to connect with attractive women on a consistent basis, so it’s more important to keep trying and experimenting than any one individual result.
• Having her see me with my family automatically gave me credibility and made her feel safe – I’m not some guy that approached her on the street. Instead, she could see that I’m out with my family and that I’m a normal person. I think this could be used in other situations – like going out to meet people with a female friend, so other women can see that I have women friends.
• I worked on the connection little by little, each time she came by our table. I would ask her some question about the menu or the way she did things and it was an easy conversation starter. That way, I could see whether I liked her personality and there was a basis for me to ask her out later. Just because a woman is attractive doesn’t automatically mean I want to go out with her.

The main issue is physical – she’s, well… fat. Yes, I think there’s no way around it. I’d say she’s about 40-50 pounds overweight.

I love the fact that she’s not self-conscious about her body and she’s not inhibited about her sexual desires. But it doesn’t change the fact that I’m just not physically turned on by her.

We went out for some ice cream first (my idea) because I didn’t want her to just come over to my place and have the pressure (on me) of having sex right away. I wanted to spend some time hanging out with her in a non-sexual way and see if the arousal level would build from there.

At the ice cream shop, I saw other women looking at us, or more specifically, at her, and I felt like Miranda from an episode of Sex and the City. In the episode, Miranda goes on a date with this incredibly handsome man and when they’re at the restaurant Miranda thinks that all the women are eyeing this hot guy that she’s with and that she’s not good looking enough for him. Well, I kind of felt the opposite – like everyone there was looking at her and wondering what I was doing with someone so unattractive. I know that doesn’t sound nice but that’s how I felt. I guess I feel I can do a lot better than her – so even though I have available sex I’m not sure it’s worth it.

We had our ice cream and then drove back to my place. I still wasn’t feeling that in the mood but I could tell she was getting more aroused. So here I had a woman that was ready to have sex with me and yet I wasn’t sure I wanted to go through with it. I wasn’t making any moves and I felt like she was being the guy by getting closer to me physically and touching me. It’s like I got to experience what it feels like to have a guys come on to women, from the women’s perspective.

When we got to my place, I thought about saying something so that we wouldn’t go through with it, but in the end decided to just do it. She kept giving me hints that she’s interested and I just finally thought “what the hell – maybe it’s worth one final time”. I somehow managed to “perform” and I made sure she really enjoyed herself but inside I was thinking that this would probably be our last time like this together. She left my place this morning after insisting that we have another go at it this morning (man, she’s got a large sexual appetite).

I don’t think she’s aware that I’d like to call it off. I’m just wondering what’s the best way to do it now – whether I should tell her that I met someone else or just not give any explanation. I just don’t want to be brutally honest with her because I think that would be unnecessarily cruel.

I don’t mean to sound like I’m boasting – I just find it amazing that my dating life has really improved in the last month – and all of it due to me just getting out there and approaching women, being more social, having fun and practicing my daily morning pick ups.

Date With My Hot Neighbor

OK, so first off I had my date with Eve, my hot neighbor. We went for coffee and had a great time connecting. We talked and laughed but I think there was a definite connection there. Turns out we have stuff in common about spirituality and philosophy of life and it was great to see that someone I found attractive had similar beliefs and values, too.

On the down side, she’s 4 years older than me and has an almost teenage son, but I’m willing to treat this as a “what if” situation. Like what if we had this nice hot fling and see where this goes

It’s kind of funny since we both live in the same building, we walked over to the coffee shop together and walked back together. We went up the elevator together and had to say our good-bye in the elevator. She said to call her if I want to get together with her again so I took that as a sign that she’s interested.

Pick Up Attempt 16 – On the Subway

I headed to a business networking event and I took the subway. I’m finding it easier and easier to strike up a conversation with a woman I’m attracted to. I noticed her coming down the stairs and getting onto a subway car. I just followed her into the same subway car and when she sat down I just asked her for directions to the place I was going. Now, I knew how to get there but I wanted to open with someone that would put her defenses down – the indirect approach that’s worked for me before. After she told me how to get to my place, I just sat relatively close to her (but not right next to her) and just started talking. She responded quite well and we ended up chatting for a good 15 minutes. As we were getting closer to her stop I just casually said, “Listen, you seem really nice and I was wondering if we could go out some time.” She smiles and I can see she thought about it but in the end she tells me that she’s recently taken a job out of town and will be moving in the next month or two. I accept her explanation and wish her well as she gets off at the next stop. I wonder, though, if I was more persistent, but in a fun way, if she would have considered having a short term fling. I mean, why not?!

Pick Up Attempt 17 – At a Networking Event

I got to my networking event and just fell into my groove. I felt like Rocky (one of my all time favorite movies, by the way) who runs and trains on the streets of Philadelphia – nothing fancy or high end, but when it comes down to a championship fight, he’s there and ready to rock. So here I was, after consistently saying hello to strangers, approaching women I meet in public and just being more social, I come to a social event – it was like taking candy from a baby – it just felt so easy being social with people who were there to socialize after spending so much time practicing/training being more social and outgoing.

I met a lot of cool people there and this really striking and very intelligent Brazilian woman. She just seemed so genuine and open and didn’t have any attitude about being beautiful – I was really amazed and drawn towards her. We talked throughout the evening, flirted, laughed and really connected. She kept touching my arm and shoulder throughout the evening but I also saw her do that with other guys so I wondered if it was a cultural thing that she’s just like that with a lot of guys.

At the end of the evening I had made up my mind I was going to ask her out – but I didn’t have the balls to just do it right there because I thought I would continue the connection by email. The Brazilian woman befriended my good friend, Yvonne, and the two of them exchanged contact info. I left the event with Yvonne and asked her if she could give me the Brazilian’s email. Well, Yvonne refused, saying that she wouldn’t do that to someone and that if I wanted to know if she would go out with me that I’d have to go back and ask her myself. And that’s exactly what I did…

I walk back to the event (we had just left) came up to the Brazilian and asked her to come over so I can talk to her privately. I just said something really simple like “I was going to contact you by email but my friend Yvonne refused to give me your address so I wanted to come back here and ask you myself: you seem really nice and someone I’d like to get to know better – would you like to go out sometime?” She was very flattered that I asked but said that she’s just getting over a big break up and isn’t ready to date yet. I took it all in stride and we continued to chat and joke around for a bit and then I left with Yvonne, again. I think there’s a definite possibility with the Brazilian because Yvonne will see here again and I’m likely to see her again if I come out to another event from the same networking group (to which the Brazilian belongs to). I felt like I just needed that extra push to go and ask out the Brazilian and Yvonne helped me out by refusing to give me her contact info.

Dating Advisor to a Female Friend

I didn’t think I would suddenly start giving dating advice to a woman, but that’s what happened with Yvonne. On the subway ride back she kept saying how she was very impressed that I just went back and asked out the Brazilian right away. I didn’t even think about it that much, to be perfectly honest. It’s like this kind of behavior is getting more ingrained and natural to me – I like that.

Yvonne is having her own problems with dating and she started asking me for advice on how to behave around guys she’s attracted to. I started telling her more and more about my dating life (up to now I hadn’t shared all my recent adventures with her) and how it’s been working for me so far and I’m having a great time. For instance, I told her all the events from today and she was floored that after seeing me ask out the Brazilian, she learned that I had also gone out on a date and asked out someone else I met on the subway all in one day.

Meanwhile, she’s having trouble making this one guy interested in her. I shared with her my ideas about practicing flirting and interacting with new people on a regular basis and how that’s helped me. She has the same problem I do – she can be very easy going and relaxed around guys she’s not that interested in but gets all tense and nervous around guys she’d like to be involved with romantically. I joked with her that we become “robots” around people we’re attracted to and how that ruins all the attraction in the other person’s eyes.

Who knows? Maybe Yvonne will become another friend with benefits. At this point, I’m just happy she can benefit from my experiences.

I’ve recently started getting out of my house in the mornings and just having a short walk around my neighborhood and saying hello to people that I pass by. I give myself about 15 minutes and make it a point to say hi to at least 5 people I pass by. It’s simple, there’s no risk of rejection, and I find it gets me into a more upbeat and social mood – the right mindset when I’m out meeting women.

I found that this simple procedure helped me already. At the end of my run a couple of evenings ago, I walked by the Starbucks coffee shop and spotted a cute female neighbor of mine (not Eve). I confidently went into the coffee shop and said hi to her and we had this really nice chat and flirted, too. Going out that morning and saying hello to people I met on the street helped me be more social and confident later in the day.

“How did she look?” I ask, trying to unsuccessfully sound like I don’t care.
“Pretty good,” he replies.
Damn. She was a fine looking woman and I never lost my attraction towards her.
“Was she with someone?” I ask, again sounding more concerned that I should be.
“She was with a girlfriend,” he answers.

So I guess she’s still single. When I think about it, we were so not right for each other. But we were together for almost 4 years and lived together 1.5 years. At one time in my life I thought she was The One. My friend mentioning her today made me think of those happy times we enjoyed when we first got together – like life was getting better and better and everything felt so right.

I haven’t talked to her since we broke up 7 months ago and I felt like I was truly over her. And yet one mention of her and some stupid thoughts come back in my head like maybe I should contact her. I’m not going to follow these thoughts but it just reminded me how much I crave that feeling of finding the right woman again.

My biggest insight of the evening was that I should stop thinking of this as picking up women and more as just talking to women. The truth is, not every woman that I want to talk to I’ll want to see again. Some I’ll find are attached, some I’ll find not that interesting or weird or unfriendly or whatever. This is a huge shift for me – now, I’m more into just talking with women while I’m out and if there’s something special about her then I’ll ask her out.

This is worth repeating: I choose the women I want to ask out, rather than hoping women choose me. Instead of hoping that an attractive woman I want to talk to will like me when I ask her out, my mindset is changing to seeing how open she is to just having a normal conversation (while we’re both being playful, fun and interesting) and how strong our connection is. Only if I’m attracted to her AND I feel a connection will I ask her out.

Before I Went Out

I got myself into the right state of mind – I meditated, said some affirmations that I developed for myself, visualized how I want to act tonight and wrote in my personal journal. This is a critical step that I didn’t do the last time I went out and I ended up feeling pretty nervous about talking to women (even though I ended up picking someone up).

On the Subway

Because I worked on my inner game – I was in a much better state of mind. I felt like I was more social and open to interacting with women tonight. I was even repeating inside my head one of my affirmations – “I can do it” over and over again. This didn’t mean I was perfect, though. While I was on the subway a smoking hot woman came on by herself and sat a few seats away from me but I chickened out of talking to her. She even got off at the same stop as I did and waited on the same connecting subway platform by herself and I still didn’t approach her. However, I kept repeating my mantra and felt that once I got to the bookstore I would be more in my element.

At the Bookstore

The Senior Citizen Lady

After feeling like I was stuck and kept getting approach anxiety I thought, “why don’t I go for a sure thing?” I decided to pick a woman I for sure wasn’t interested in and talk to her – that way the pressure is way off. So I went through the magazine section and at the travel magazines see this harmless looking elderly lady with a walker, looking at the travel magazines. “Have you found any interesting places to go?” I ask her in a friendly way. “Oh, I’ve been all over the world in my younger days,” she replies. We then spend the next 5-10 minutes just chatting about her world travels and she tells which were the most interesting places she went to – south island of New Zealand was one of her favorites.

The Hot Woman with Cute Little Dog

After my warm up, I felt more at ease. I wandered to the bottom floor of the store and notice a really attractive woman reading on the floor with a cute little Yorkshire Terrier on her lap – perfect opportunity. I choose a route to approach her so that I will “suddenly” see her as I round a corner. As I round a corner I do my best surprised look when I spot her with her dog. She looks up at me and smiles and I say something really clever like “Hi!” She says hi back in a very friendly way. “This is quite a surprise to see someone with their dog in a bookstore.” She starts telling me about how she got the Yorkshire a short while ago and she’s looking for a book on how to take care of it. She’s seems very friendly and open. She lets me hold the dog within a few minutes of meeting her and I play with him – a really cute and friendly dog, I must say. He’s wearing a very cute vest with the flag on him and I comment how he’s very fashionable. We talked for about 5-10 minutes after which time she decides on which book she wants and bids me farewell. I debated whether to ask her out but I didn’t because I felt like even though we had a great start, I just didn’t feel the same connection to her as I would have liked. Maybe part of it was that I was intimated by her good looks so I might not have been as relaxed but I also think that the connection just wasn’t there.

The Insight – Just Talk to Women Without Any Pressure To Ask Them Out

After the woman with the dog left I just stood there thinking about what just happened. I just initiated a conversation with a very attractive woman and it went relatively well and I didn’t ask her out and I didn’t feel bad about it. I kind of felt like I saved myself from a boring date. Then a light bulb went on over my head – I don’t have to ask out every attractive woman I meet! This was like a Eureka moment for me. I suddenly felt all this pressure off of my shoulders. I could just talk with women, attractive and unattractive, and just ask out the ones I was attracted to AND that I had a real connection with. Just because a woman happens to be hot doesn’t automatically mean I want to go out with her! Brilliant! I suddenly felt my whole attitude changing – I wasn’t “approaching” or “picking up” women anymore. No, instead I was just talking to them, in a fun and friendly way, and seeing if they qualified for me to ask them out.

The Cute Store Clerk

Now that I felt all this pressure off of me to ask women out, I just started looking for other women to talk to. I started a conversation with a one of the female staff (plain looking) and then another one (cute). I wasn’t interested in going out with either of them but it just felt liberating to start talking to them without the pressure of asking them out.

The Unfriendly Magazine Reader

I spotted a not-so-attractive woman reading a People magazine in a very serious way. Now, I’ve got nothing against that magazine but it just seemed little odd that she’d be reading it with such intensity – as if she’s trying to find the secret of life or something. I wander over and start looking at the books close to her. I start the conversation with something I can’t remember anymore. She just gives me a one line grunt of an answer. OK, not that friendly of a person. I continue to look at the books and then just ask out of sheer curiosity “Do you read that magazine just for fun or are you looking for something in particular?” She answers in this condescending tone “I read it because of the fashions” and then rolls her eyes like I’ve just insulted her mother or something. You know, I just smiled inside knowing that this woman was a) so not right for me and b) had a really negative attitude. It’s like I felt good that she showed me her bad side so quickly so I can move on to other women to talk to.

The Attractive Venezuelan

As it’s getting to closing time, I wander around the magazine section again and spot this really attractive woman reading a fashion magazine. I pick up another magazine close by and make some remark that I can’t remember anymore. She replies with just a “yes” (so I guess I didn’t ask an open ended question) but I notice that she’s got a Spanish accent. So I ask her about it and that starts a really cool conversation. Turns out she’s originally from Venezuela and has been living here for a few years. She also tells me she met her husband here and that they bought a house recently. She’s very warm and open and friendly. It’s just a pleasure talking with her, even though I know we’re never going to go out or have sex. She even asks me if I go to this bookstore often so we could run into each other again. Really great way to end the evening at the bookstore.

Subway on the Way Back Home

Now that I had my new attitude I didn’t care nearly as much of what women thought of my approaches. As I stood on the subway platform waiting for the subway ride home this really attractive woman walks by me and stands about 20 feet away. She’s by herself and wearing an iPod. Now, I didn’t know if she was the woman for me but I thought why not just talk to her and forget about asking her out – let’s first see if she’s worth asking out in the first place.

I walk up closer to her and say something very witty like “Hi!” and smile warmly. She smiles back and says hi. I ask her if she’s wearing an iPod since I can only see the white headphones. She takes her headphones off and says that it is indeed an iPod. I note that she’s pretty open and is smiling warmly when she’s speaking so I continue talking with her. We go on talking about where she goes to college (out of town) and how she’s back in town for the summer. When the subway comes we sit next to each other as if we know each other. I find I’m just chilling and having fun with her – I’m not sure I want to ask her out (she’s a little young for me) but I find it interesting to talk to her and find out more about her. As we get onto the subway and sit together I give her an out by saying “Listen, I don’t know if you wanted to just listen to your iPod instead of talking to some guy you just met, but I thought it would be more fun talking to someone while we’re on the subway anyway.” She tells me she’s OK talking so we continue to talk – mostly about what she’s studying in college and how her school has a reputation for being a party school. It’s just easy and fun talking to her and it makes the subway ride home a lot more interesting. Her stop comes before mine and we say good-bye to each other. I decide not to ask her out – yes, I suppose, she could have been good friends with benefits material especially since she’s here for the summer but I didn’t feel any great urge to ask her out, mostly because of the age difference.

What I’m Feeling

My feelings and ideas about picking up and meeting women continue to evolve. I feel like I’m no longer automatically asking out any woman I happen to meet in public, since I’m meeting a good number of women these days. I feel like I can be more choosy and see if the woman is worth asking out. Sure, I’ve still got a lot more to learn as far as building strong connections with really attractive women but I think that’ll come.

I’ve also been thinking about setting some daily assignment or challenge – like talking to at least one or two female strangers a day. I’m not ready to commit to it but it’s something that might be fun to incorporate into my daily habits.

Last night I went to the same bookstore I was at a couple of weeks ago, where I had found a diamond earring, while attempting to pick up a couple of women. Turns out no one claimed them and the store manager called me to say I could come and pick the earring up.

I took the subway to the bookstore but wasn’t feeling particularly social. I don’t know why, since I had just made a move on a female friend of mine a couple of days ago and my last pick up attempt went very well. For some reason, I just wasn’t into talking with strangers on the subway. There were a couple of women I could’ve definitely started talking to but I chickened out and just sat silent and observed everyone else around me on the way to the bookstore.

When I got to the bookstore, I picked up the earring and headed upstairs to browse through books and see if I could start talking to someone. There were a lot of people in the store – many more than the last time I was there. I just wasn’t feeling that confident and I couldn’t shake the feeling. I saw a couple of women that I could’ve approached but I chickened out. I decided to console myself by just looking for some books to read for myself and forgetting about picking anybody up for the time being.

I headed to the philosophy section and start browsing. A few minutes pass and I suddenly notice there’s a woman who’s browsing really close to me. I perk up and wonder if I should start to say anything. But I don’t, which just causes me to feel worse and I decide to go back to my book browsing.

Then I move to the history section and start looking through a World War 2 book. I’m a big fan of history, especially 20th century, so this was something I really enjoyed. I must have stood there for a good 10 minutes just going through the book and consoling myself that I didn’t have to pick anyone up tonight. After all, maybe I deserved a break. Maybe other people wouldn’t consider this normal, to consistently go to public places to try and pick up women.

As I’m rationalizing my inaction, I hear the voice of a woman asking one of the store clerks for help finding a book. As it turns out, the book she was looking for was very close to where I was standing. She thanks the store clerk for the help and starts looking at the book. I get a look at her. She’s semi attractive. Not gorgeous, but definitely not ugly. Definite friends with benefits material and there’s a long shot for something more serious with her. OK, this must be a sign from above because a) I didn’t have to walk up to her since her book happened to be right next to me and b) the book’s title is very intriguing so it’s a great conversation starter.

I open with a question about the book. I honestly can’t remember exactly what I said but I think it was a comment about the funny title of the book. She looks up and tells me more about it. I can see she’s very intelligent right away. She starts telling me about all these other books that she’s really into, and she tells me how she’s a big fan of world history (which is a big plus in my books since I love history as well). I can see she’s a very passionate person with strong convictions. I’m actually quite pleasantly surprised to meet someone so intelligent and passionate and open.

After 10 minutes of non-stop talking, her female friend comes by to see if she’s ready to leave, but the woman tells her friend that she’ll meet up with her later. I take that as a very positive sign that she’s interested in me, since she could have used that as the perfect excuse to wrap things up with me and leave with her friend.

I feel like this would be a good opportunity to ask her to go for coffee and continue this further. So I ask, ever so casually, “Listen, it’s really interesting talking with you… what do you say we continue this over coffee?” She smiles but says she has to see her friend shortly. But then she gives me her business card and says to call her so we can get together another time. Alright, so I’m in.

We finally do a name introduction – she’s Anna. We then continue to talk… and talk… and talk. We literally talked non-stop for about an hour and half – until the store closed! She told me about her family, her upbringing, her beliefs, and we shared some funny stories. We had a lot of fun just sharing and talking and connecting. When the store closed, we went outside and talked for a few more minutes on the street. I offered to walk her over to her friend’s place but she said she could manage fine by herself. Now that I think about it, that probably wasn’t a great move on my part – after all, she only met me, and here I was offering to walk alone with her late in the evening. She tells me how it was most unexpected to meet me and my intuition is telling me that she’s definitely interested to go out. She tells me how she’s pleasantly surprised about our serendipitous meeting. I’m feeling great, too, but I wasn’t going to tell her “Oh, yeah, you’re my 15th pick up attempt and I came here to practice, and guess what – I finally succeeded with you!” We bid each other farewell and she goes off to her friend’s house while I go back home on the subway.

You’d think I’d be jumping for joy and be one of the happiest people on earth. Don’t get me wrong – I’m happy and really proud of the fact that I stuck through it and continued to pursue this goal despite the setbacks. But I’m not completely over the moon. One reason, is that I felt I lucked out because Anna happened to be browsing right next to me. I didn’t approach the women on the subway or the other women I saw at the bookstore before I started talking to Anna. Also, she wasn’t physically as attractive as I would have liked.

On the postive side, my feelings about dating are evolving. The fact that I went out tonight and got a phone number of someone that was a complete stranger just a few hours earlier is a feeling of great empowerment. It’s like I don’t have to depend anymore on women that I meet through traditional channels – through friends, dating sites, work, school, etc. The fact that I can just go out and meet new women out in public makes me feel… free, more attractive, independent and successful. I feel like I don’t have to accept crap from flaky women that don’t want to commit to a date or feeling scared of rejection from some woman that I really like. If I know I can go out and easily meet more women, then it makes me more relaxed and not feel like my happiness is dependent on how one or two women will respond to my overtures. It makes me care less about the outcome with any one woman, which, ironically, improves my chances of hooking up with women. I don’t have that desperate or determined attitude behind my words or actions and women can sense that I’m relaxed, but still engaged, in the interactions with them. This is the reason why I feel it’s necessary for me to date multiple women at the same time.

Things I learned

• Don’t go out with the goal of picking up. Tonight, I just wanted to connect with a new woman through a conversation, that’s all. If I happened to pick someone up, then great, but it wasn’t my goal. This concept is counter intuitive because we use goal setting in so many other areas of our lives. But for some reason, straight goal setting doesn’t seem to work as well with dating and picking up. The indirect approach seems to work better.
• Warm up if I’m feeling out of practice with picking up women. Last night, I felt like I couldn’t just jump in and start talking to women I was attracted to right away. I could have warmed up beforehand by chatting with other people that I wasn’t interested in – older women, men, unattractive women, etc. It’s like stretching before you start exercising.

A couple of nights ago, we went to an event together. When we talked during the day, she told me how she had done her hair differently and that I might not recognize her when I see her. I joked with her that I’ll just look for the hottest woman at our meeting spot and I’ll start chatting her up and trying to get her number – I think she really liked that indirect compliment.

On the way to the event we did our usual non-stop talking – open, honest, funny, real – just having fun hanging out. I thought about the possibility of doing a friends with benefits arrangement with her in the past but have always stopped myself because I thought I wasn’t that into her or that it could get complicated.

Anyway, we were talking about our personal lives and she asks me if I’m seeing anybody right now. I tell her about my blind date from hell and how I’m just dating right now. She asks me what exactly that means and I just say I’m going out with different women. She digs further and asks if that means having sex with women, too, and I just answer with “if there’s a mutual desire for that kind of arrangement”. Later on, she boasts how a guy recently made a pass at her and how she rarely gets guys making passes at her. Personally, I think guys don’t see beyond the walls she puts up around her and because she’s not gorgeous or pretty in the traditional sense, they don’t pursue her. Inside, I’m thinking that it’s really too bad this woman doesn’t feel desired and sexy because she’s got a beauty about her that’s just not immediately evident. I joke with her that she needs to get laid and she complains that it’s been ages since that’s happened. As I’m wondering whether this is an open invitation to pursue things further with her, she adds, “But I can’t just have casual sex with someone. It’s all or nothing with me.”

On the way back from the event, we take the subway together and continue joking around and talking. In the back of my mind I’m wondering whether I should just do it and make a move just to see how she’d react. I’m not getting the same signs Angela gave me when we first got together for coffee, but at the same time she’s continuing to talk a lot about herself and is really opening up emotionally. When we get out of the subway, we get into her parked car and continue to talk. She’d doing most of the talking (about how she doubts her own abilities) and I’m just sitting there half listening and half wondering what it would be like to just kiss her. Finally, when she’s paused for some breath, I start moving closer to her and getting ready to kiss her. She reacts with “Whoa! What are you doing? Were you about to kiss me?!” and gets a surprised and weird look on her face.

At this point, things could have gone in a couple of directions – the awkward or the laid back route. In previous times, I might have felt unsure of what to do next, but tonight I just reacted in an easy going and laid back way. I treated the whole incident like it was no big deal. Now if I reacted by getting all embarrassed or self conscious, she would have felt really awkward and the evening would have ended on a down note. This way, we just continued talking and she now knows that I find her attractive and am open to the idea of being physically intimate with her. Knowing that she’s desired by a man (i.e. me) gives her a high so I think she feels better about our interaction.

When she asked me “What are you doing?!” as I was going for the kiss, I just replied with, “I wanted you to know that you are desired and that I find you attractive and that I think you have it in you to succeed.” I meant that and I wasn’t just trying to feed her a line. I guess I wanted her to know that she’s got a lot going for her and she should believe in herself more. I also knew that she doubted her own beauty and I wanted to reaffirm that in her.

We continued talking and she dropped me off at my car and I bid her farewell. I think things between us are back to normal and I really don’t think they’ll be any weirdness that often results after one side makes an unreciprocated overture.

I guess I feel that every woman I interact with should feel respected and positive about the interaction. I didn’t want her to think I just wanted to get laid and nothing more. The truth is, I really wanted her feel desired sexually by a man. Maybe that scared her because it’s been a while since she’s been physically intimate with someone. Either way, I’ve put my intentions out there and we’ll see if anything develops.

I wrote her an email at almost midnight, mostly because I told her I’d be contacting her this week and hadn’t yet. So I just wanted to send her a quick email to say hi and to see how she’s doing. I thought that maybe we could get together sometime next week since I wanted to keep this weekend free for practicing pick ups and getting together with my friends.

Not 10 minutes after I send her the email, I get a phone call and it’s her! Wow… I like women that are enthusiastic but that kind of freaked me out. I was getting ready to go to bed and didn’t expect anyone to call that late so she startled me.

Note to the women out there – if a guy is only communicating with you once a week (phone or email) and he sends you an email to say hi, that doesn’t mean he wants you to call him right away.

She’s very enthusiastic when she calls and explains that she’s calling so late because she just got my email and since I sent it only a few minutes before that she figured I’d still be up. She asks me about my day and my weekend, tells me about her goings on and generally seems very happy to talk to me. We joke around and have a good time just laughing and catching up but inside I’m thinking that the inevitable question will come up. Sure enough, she eventually asks, “So… when can we get together?” I was kind of dreading that question. I say something to the effect of “Why don’t we get together sometime next week?” There’s a pause on her end… and then a disappointed “Oh…OK”. She was, understandably, hoping that we’d get together this upcoming weekend, since we didn’t get together last weekend. But I don’t want to give Angela the impression that we’re dating or boyfriend/girlfriend and if we start hanging out every week, even if it’s just as friends with benefits, I think she’ll start to interpret it that way.

In some ways, I feel I’m doing the same thing to Angela that Nancy did to me, where I felt she was avoiding making a firm commitment to getting together with me. But I honestly feel it would be better for me in the long term to keep getting out there and approaching more women rather then settling for the sure thing of sex with Angela.

I’ve been dragging my feet on making a hard decision with Angela and some of you have been wondering what’s going with this. The truth is, I’m torn between two choices:

a) Cutting the sex off completely but still spending time with her as a friend
b) Cutting the sex back to an occasional, but nor regular, occurrence

Originally, I thought I wanted a) but now I’m wondering if b) would be a better option. It’s contagious to hear her enthusiasm – when we talked she asked when she would get her “next fill” of me and I guess it makes me feel good as a man that this woman is very interested in continuing to have sex with me (not to toot my own horn or anything). I think I opened up a passion inside her that was dormant for a while – and I think she’s truly happier than she was before. However, I’m not sure I’m the man to continue to keep that passion alive for her.

This is exactly what I mean when I say that I seem to attract women I’m somewhat, but not deeply, attracted to.

We left things that we would get together next week, during a weeknight, for a coffee. I should probably decide whether I want that get together to end up at my place.

The bookstore has a Starbucks coffee shop attached to it so I walk through the coffee shop first, seeing if there are any women I can approach there. I even have a question I’m ready to ask (“is there a power outlet for a laptop here?”) if I see her. I see two women sitting together and chatting very intensely – I’m not ready for that kind of approach yet so I move on and go into the bookstore.

As I step out of the coffee shop and into the bookstore, I notice this older lady (45ish) giving me a look – you know, “the look”, which kind of startled me, but maybe I’m getting more attune to these signs from women now. She was there with her husband and I wasn’t really that interested anyway, so I smiled – warmly, openly, but continued to move on. I move through the aisles, casually glancing at the books (I love bookstores so it’s always a treat to go to one even if I’m not practicing pick up). I notice another older woman (55ish) by the best seller non-fiction section and I decide that I’ll just say hello to her – no pick up, no “maybe we can go for coffee”, just a simple conversation. I open the conversation with “is there anything good?” She was reading some book with an intense look. She looks up and smiles and says, “Yes, there are lots to choose from.” We politely talk for another minute or two and I move on feeling like I’m ready to talk with women that I’m actually interested in. It’s almost like I need to warm up before the main event – like stretching before running.

I move to the philosophy section and I see two young women there. One is relatively attractive, in a normal way (certainly not hot) and the other is the “unattractive fat friend”. They seem like they’re in their early to mid twenties and they’re wearing long skirts and the attractive one is wearing a Star of David around her neck – what is it with me and finding religous Jewish women for pick ups?

Honestly, I wasn’t super interested but I think of it as a great opportunity to practice. So I open with a question about the philosophy book the attractive one is reading – something like, “Is that an interesting book?” She responds very openly and tells me more about it. We start talking casually about philosophy – turns out she was a philosophy major but is now a teacher. We must have talked for a good 5-10 minutes while her fat friend was mostly silently looking on. I didn’t feel the pressure to ask them to join me for coffee or to get their phone numbers, which, ironically, made the whole interaction go a lot smoother. I’ve commented on this phenomenon before, where the less I care, the better results I seem to get.

Finally, she says that they should get going as they have a lot of books to purchase, so I bid them farewell. I was debating whether to ask them to join me for coffee just for the sake of practice but decided not to.

So then I keep wondering the store and spot this rather attractive (late 20s to early 30s) woman in the travel section. Again, I try to be subtle and not “corner” her by starting to browse right next to her. I even browse some books close to her section but not in the same aisle. She then moves to the nearby health section, which is in an open space. I casually start looking in the health section, too, but a good 10-15 feet away – feeling out the vibes from her… Then she leaves the health section, which I interpret to mean she’s not interested. This phenomenon has happened to me before and I’m starting to think of it as subtle way from women to say their not interested in being approached. (Do you agree?)

So I’m ready to call it the night when, lo and behold, I see the original two women that I talked to at the philosophy section. I walk over to them, now as if we know each other, and ask “So what happened, I thought you guys were going to leave?” The attractive one says they couldn’t help themselves and got sucked into looking at more books. So then I decide to go for it – I ask, ever so casually, “Listen, I was going to go to Starbucks to grab a drink and I thought maybe you guys could join me.” They both smile and look at each other with that girlie “oh my God, I can’t believe he just asked us out” look, but they bow out, saying they have to purchase the books and besides, the coffee shop will be closing in 15 minutes. I look at my watch and fake a “Oh, I guess you’re right.” I tell them it was nice to meet them and bid them farewell – again. I notice the fat friend is smiling at the attractive one and giving her that “eye look”, which I interpret to mean that they’ll have lots to talk about after they leave the store.

Things I learned

• Being indirect seems to work better than being direct. By talking about something else besides the woman, puts her more at ease. Instead of saying how I find her attractive or interesting or whatever, I can discuss the book that she’s reading or what she studied in college and through that get the vibes of whether she’s interested in continuing this further. This is a big realization and I think I’ll use this more often from now on. Women just aren’t the same as guys – they have a much stronger sense of danger, so saying something direct like “You look interesting and I wanted to talk to you” right off the bat can cause alarm bells to go off in their heads – not what I want.
• Not caring as much about the outcome makes the interaction a lot more fun and easy going. This is a difficult one to grasp for me, and I think a lot of guys, so by no means am I an expert at this. But I’m getting just a taste of what it means to truly not care about the outcome and how women can pick up on that. When I talked to the two women tonight, I was just curious to see where it would go and I just wanted to make a connection – that’s it. I didn’t want to sleep with them or even go out with them and I wasn’t even sure about whether to ask them out. And yet I felt I was in some ways pretty close to an actual pick up tonight.
• Include all the women in the group. I could have made the fat friend feel more included while I was talking with the attractive one. I had nothing against her and she seemed nice but when she was sitting rather quietly listening to us interact, I could have made her feel more included. I did ask her a few questions but she was mostly on the outside watching the two of us interact. As an added benefit, including her in our conversation would have served me well when I finally popped the question of whether they want to join me for a drink because then I would’ve befriended both of them so all three of us could have had a fun time talking.

Anyway, since we met, I’ve gone through a few relationships and she’s broken up with her boyfriend. So I was thinking what better opportunity to get together and just hang out just the two of us. Hell, she even invited me to her birthday a few months back and I’m not even a friend – just someone that she met by accident and who she’s been corresponding with for a year mostly by email.

So you can imagine my disappointment and bewilderment when I was talking to her the other day and suggested (for the third time) that we get together. Her response – “this is a really busy week for me – let’s try for maybe something next week.” Yeah… whatever… This wasn’t the first time she gave me that line. We talked a few weeks back and her response was the same. It’s kind of funny – that we’ve known each other for about a year and yet have only physically seen each other on about three occasions. But what’s up with that? If she’s not interested, then just say so! I can take it. What’s the point of stringing this along? In case nothing better comes along then she’ll agree to get together?

I guess her response got me down because I thought we could be a good match. But I also realize that that line of thinking is what gets me into problems – I build up these expectations of what “could be” with some woman I’ve idealized and then I put too much pressure on myself for making it work when I interact with her, which inevitably causes me to not be as relaxed and easy going as I am with women I’m not as attracted to, which causes these women to string me along by saying “I can’t this week, but maybe the week after.”

See, I tend to have this “problem” where I can attract women I’m somewhat or not attracted to and yet have trouble attracting the women I truly desire. It’s ironic, but with the women I’m not as attracted to, I’m more relaxed, easy going, funny… more myself. And that’s what probably wins them over. But with women I’m very attracted to, I’m less bold and I get more uptight and self-conscious which leads to responses like “I can’t this week, but maybe the week after.”

On top of this crap, my hot neighbor, Eve, again postponed our date because she’s been really sick. On top of that this woman that I wrote to from an online dating site hasn’t replied. On top of that I still have to figure out what to do with Angela and how to end or alter our friends with benefits arrangement.

I think my main task should be finding more women to go out with and continuing to practice my pick-ups. I’m guessing this is a common problem for guys – that there are one or two women that we have our hearts set on and there aren’t other women readily available for interaction. I’m not saying you have to be Hugh Hefner who’s constantly surrounded by women, but I do think having other dating options is very important – especially if you want to date women that you’re very attracted to. I think that if I knew I could go out and easily meet high quality women in a short amount of time, I’d basically call Nancy on her B.S. and move onto other women. Right now, as far as I’m concerned, she’s out of the picture – I’m not going to ask her out again – too much trouble for a single woman.

As I was finishing my run where I tried to pick up two women, I ran by the Starbucks coffee shop close to my place to see if there was someone inside I could practice on. The place was fairly empty on a Saturday afternoon, but I noticed one somewhat attractive woman (late teens to early 20s) sitting by herself with papers around her – obviously studying. Now, I’ve mentioned in past posts how I feel that women who study at coffee shops are partly there to socialize, too, so I figure why not and see if she’s open to talking.

I come in to the Starbucks at the end of my run – I’m pretty tired and just order a water. I flirt a little bit with the female Barista and proceed to walk over to the table next to the woman I’m interested in. I sit perpendicular to her, so I’m not facing her directly but my back isn’t to her either. I don’t want to just start talking to her right away, since I tried that before with mediocre results.

So I sit there relaxing and drinking my water. I glance over at her now and again to see if she looks up. She doesn’t. She’s totally focussed on her book and the notes she’s taking. I look at the book – some kind of Calculus book. Cool, I took Calculus, maybe we can talk about integrals and derivatives while our body language can talk about hooking up and having some fun. After a few more minutes I wonder whether I’m just wasting time and the situation is becoming awkward – let’s just do this already.

So to get out of my inactive state I get up and walk over to the trash bin to throw out some napkins. As I get back to my table I glance over at her, who’s just at the table next to mine, and just ask, “Is that an interesting book?” She doesn’t look up at all. It was as if I didn’t say anything. She totally, completely, utterly ignores me. Now I notice that she’s wearing one headphone but it looked like only one of them was in. Besides, even if she was wearing both of them, I think she would notice if someone said something to her. So I ask again “Is that an interesting book you’re reading?” Nothing… Silence…. She just continues staring into her book… Wow… I never had that happen to me before. OK, so that was different. I debate whether to walk up closer to her and ask again or say something else to her, but I just figured what’s the point – she’s obviously not interested.

Things I learned

• Start talking to her sooner, but not right away. Maybe she would have felt less weird if I talked to her a minute after I came over to sit by the table next to hers. That way, I’m not startling her since she’ll be aware of my presence but I’m not breaking a long moment of silence by suddenly asking her a question.
• Have more fun! Maybe she was ignoring me but so what! I think I could have started talking to her in a more open way – like making a joke about the book or pretending like I was going to give her a Calculus test right there or pretending that I was someone looking for a Calculus tutor. Just something to break her out of her shell. This is something that will develop more as I keep making more approaches.