I approached and asked out three women on Saturday – two on the subway and one at the museum.

I went with my good friend Xavier to the museum on Saturday. He’s a single dad and he had his son, Nick, this weekend so we went the three of us. On the way to the museum I took the subway and I was looking for more opportunities to practice. I started talking with an older lady for a couple of stops – no flirting, just normal friendly talking. She got off after a couple of stops. A few stops later, this stunning woman gets on and she’s listening to an iPod. She sits across the aisle from me and I’m trying to get some eye contact established. She’s not helping – she’s completely looking down the whole time. I was going to ask her about her iPod because I don’t have one and I was thinking of buying one. But she just would not look up. I thought I would wait and not talk to her right away since I realize now that can startle women but it was getting a bit ridiculous – a few stops had passed and I still hadn’t said a word. So I decided to let this one go – this was too advanced for me – she was across the aisle, not looking up and didn’t seem that friendly. Maybe when I’m better at this pick up thing I’ll try situations like this, but not today.

Pickup Attempt 1 – Subway

After a few more stops, another really hot woman comes on and sits right next to me! She’s reading a magazine and is very engaged but something about her tells me she’s more friendly and open than hot woman #1 with the iPod. So after about a minute of her reading beside me I just say “I can’t help but read the magazine, too” since she had it open in such a way that I could see the article, too. She replies in a warm way and tells me more about the story she’s reading. I ask her about the magazine and she tells me it’s GQ and I make some comment how I thought that was a man’s magazine. So then she tells me she’s in the magazine advertising industry and she needs to keep up with the content of a lot of magazines. She tells me she does some work for Cosmopolitan and we joke and make some digs at that magazine and how it’s kind of a trashy woman’s magazine (no offence to all the Cosmo lovers out there). We’re having this nice, friendly chat but my stop is coming up so I step it up a notch and tell her “my stop is coming up but I wanted to ask you if you’d like to go out some time”. She smiles very warmly but says she’s involved with someone. I make no big deal out of it and we continue joking and talking until the subway train comes to my stop. I tell her now she has a story to tell her boyfriend and I also tell her that she’s a very beautiful woman that could be on the cover of Cosmo herself (which I genuinely feel). She takes the compliment well, my stop arrives and we bid each other farewell.

Pickup Attempt 2 – Subway

After I get off the train, I had to make a connection on another subway line. I get to the other platform and start waiting. It’s crowded and I just zone out a little, thinking about what just transpired – I’m pretty happy with how things went but I think I could have flirted a bit more with her – played it less safe. When I awake from my zone out session, I notice this really cute woman standing next to me on the platform. We’re both waiting on a crowded platform. She doesn’t look like she’s being occupied by anything so I open with “I think it would be faster to walk to where I need to go than wait for this subway.” I’m joking, of course, and she picks up on it and replies in a warm way. She asks me where I’m going and I tell her to the museum. We continue talking until our train arrives – I ask her about what she does and she tells me she’s in university studying dancing which is kind of cool. I tell her about my background as an amateur actor and there’s a good connection going. The train arrives and we board – we’re talking and flirting a little. The problem, though, is that I have to get off in just two stops so I don’t have much time to build a connection with her. As my station is coming up next, I tell her that I’ll have to be getting off soon but it was really nice to talk to her and I’d like to go out with her sometime. But she, just like the last one, tells me she’s involved with someone. She does tell me though that maybe we’ll run into each other again. I answer with “yeah, right, what are the chances of that happening?” Then she tells me she’s performing in a dance show at a local dance theatre implying I can come check it out and even tells me the name of it. I ask her in this genuinely puzzled/intrigued way “You’re not someone famous, are you?” something about the way she mentioned the dance show that she’s involved in made me wonder if it was a well known show. She just smiles warmly and tries to be humble with some comment I can’t remember anymore. We joke and talk the rest of the way to my stop. I exit the train and she rides off.

By the time I end up meeting Xavier and his son, Nick, at the museum I’ve already asked out two women today, and that’s even before the even where I was supposed to have practiced asking women out. That’s more than I would normally have asked out in a month, before I started working on my pick up skills. I’m feeling pretty good at doing something (chatting up attractive female strangers) that I thought was way beyond me just a few weeks ago. At the same time, I feel like I have a lot more progress to make – like getting over this boyfriend response that I seem to be getting a lot of. Sure, some of them might have boyfriends, but my cynical side is telling me that many women just use that as an excuse if they’re unsure about a guy or the approach he’s taken.

Pickup Attempt 3 – Museum

As we were exiting one of the exhibits, I spot this really attractive woman looking at one of the ancient artifacts on display, behind a glass enclosure. She’s by herself, or seems to be with a female friend who’s nearby and I don’t see a guy around. Perfect… I tell Xavier that I’ll catch up with him in a few minutes and casually make my way over to the same piece she’s looking at. She’s reading the plaque and I just open with “what do you think they were using that for?” I honestly wanted to know because it was a strange looking piece and the plaque didn’t say what it was used for in ancient times. She replies that she’s not sure and I start speculating on all the different uses that it could be used for – kind of silly things but nothing crude. We share a few laughs and talk a bit more. Turns out she’s here with her sister and she doesn’t mention any husband or boyfriend. I tell her that I’m here with my friend and his son. We’re talking, smiling, flirting and it’s going well. After a few minutes, I realize that I told Xavier I would be a few minutes so I tell her that I have to get back to my friend but I ask her if she’d like to go for a coffee sometime. Then she tells me she’s involved with someone (man, I’m hearing this often). I wrap things up with her by wishing her well and I might have complimented her, too, I don’t remember. She really was very attractive.

Other Pickup Practice Notes

I chatted up many of the female volunteers at the museum. I got the vibes that from one of them that she might be interested in going out but I honestly wasn’t that attracted to her and decided to just leave it as a nice flirting practice. I also started conversations with multiple female visitors at the museum. One of them was this really tall, really attractive woman with a kid. I wasn’t sure if she’s a single mom (my friend Xavier seems to think he’s an expert at spotting which ones are the single moms and which ones are married) and I was too chicken to really flirt with her beyond just very “safe” talking about the way her child was playing in one of the children activities.

Later in the day, after the museum, I stopped by a drug store and in line I ended up chatting with a cute woman who’s a bit older than me – maybe 5-10 years. She was getting a single bag of chips and I opened with some comment about how she just had the munchies for a single bag of chips. She was very friendly and told me how she’s baby-sitting her nieces and nephews so the chips are for her when they go to sleep. She told me how she’s being very disciplined and getting just one bag even though she really likes them I told her that she doesn’t have to worry about maintaining her figure and gestured with my hand up and down towards her body that she’s got a very nice figure, which I honestly thought she has. She really smiled and lit up when I said that and I felt that if I wanted to I could probably get her number or even meet up with her later that night. But, I had a date with Angela tonight and she was staying over and besides, I wasn’t that into her. I just thought of it as another chance to practice flirting and of making a woman’s day. I think she felt really good after our interaction – she went into a store to get some chips, her guilty pleasure, and she comes out feeling like she’s a sexy woman.

Things That I can Improve On

  • Take more time with each connection. I could have talked to the girl at the museum longer before asking her out. It wouldn’t have been a big deal if I took longer to join up with Xavier and Nick and spent more time talking with her. That way, she might have felt more comfortable in saying yes.
  • Start using casual, non-sexual, touching in my conversations with women. This is a hard one to start doing. After all, women are not used to strangers touching them and I’m not intending to do anything inappropriate. At the same time, I think it would help break down some barriers some of these women are feeling when I ask them out. I’m not talking about leaving my hand on their shoulders or anything. Just really short, casual touches while we’re talking – to deepen the connection between us. I get the feeling that many women might want to say yes to me but stop themselves because it seems too fast to just say yes to someone you just met. I think that light, short, casual touching while we’re talking can help make women feel more comfortable.

Things That Worked Well For Me

  • Stayed relatively relaxed for most of the interactions. OK, I was too nervous to ask out the hot iPod woman on the subway and one of the women in the museum but overall, I’m fairly relaxed when I start talking to women I meet.
  • Complimenting or saying something slightly sexual. I’m not talking about being crass, but at the same time, I think it’s a mistake for guys to be totally asexual when talking with women they’re attracted to. I think you should let them know that you find them attractive – that way, she’s clear about your intentions, which I think is a good thing. I told the woman in the subway that she was very beautiful and could be on the cover of Cosmo herself; I told the lady at the drug store that she didn’t have to worry about her figure and feel guilty about getting the bag of chips. I meant each of those compliments and I wanted them to know that I find them attractive.