After I came back from my run, I quickly showered and got dressed and went out to the bookstore to see if I could practice meeting more women. I’m just feeling this new determination to complete my approaching women challenge. I think this is kind of interesting motivator that I could use in other areas of my life.

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.
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