So I guess after my 14 attempts at picking up a woman, you’d figure the stars were finally aligned or my numbers came up or something happened to create a successful pick up. Yes, that’s right – last night, I, Mr. Dating Guy, successfully managed to initiate a conversation with a woman I’d never met before and get her phone number.

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.

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