Women, Women and More Women: Date With Hot Neighbor, Pick Up

Yesterday was an insane day as far as dating goes – I finally went on a date with my hot neighbor Eve, I tried to pick up a woman I met on the subway, I asked out another woman I met at an evening business networking event and I confirmed plans for Saturday with Angela, my friend with benefits. Oh, and I also had this long talk about dating with my female friend, Yvonne, and she’s now calling me her dating guru.

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.