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Last night I started conversations with 6 women and I didn’t ask out any of them. I could have – some of them were quite attractive and even friendly but I just sensed that the chemistry wasn’t right or they were too young or involved with someone or just unattractive.

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.


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