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The approach went against what most guys advise, which is that outdoor nighttime approaches are too scary and can easily creep a girl out. This is how I managed to not creep her out:
First, I was there with my female friend. The woman was a cougar, but cute. I'd definitely sleep with her. She was walking her dog in the park, and my friend was like "aww what a cute dog." She seemed very friendly.
So my friend and I were legitimately talking about a problem of hers, which is that she comes off too clingy and scares guys off after the first date. It's comforting to note that some women have this problem too, it's not just guys. In particular, she asked me how she should signal to a guy that he should get her number, without coming off too masculine and dominant about it. I told her she should ask the cougar for her advice. She said she didn't feel like it, but I could ask her.
So that's exactly what I did. I walked up to her very relaxed. At this point she was at a better lit part of the park, which was right by a shopping mall. I used the very real situation as an opener, and this is why it was so natural and believable to her. BTW I'd advise any guy to think of openers that really pertain to your life, like this one, which involve actual concerns about relationships that are coming from your real life female friends. Instead of being the emotional tampon for your friends, use their legitimate concerns to open women.
She got really into it. She wondered why I'd chosen her of all women to ask, because she said she had some of the same issues. She thought about it, and said "No, not exactly the same. I just got out of an 8 year relationship, and I think my problem is more... not choosing wisely." I said "You mean, he didn't appreciate you?" She said "Yes" and I said "That must suck." Notice I wasn't overeager to show my emotional support, I was just showing that I'm a good listener. I was also showing that I'm a good guy without coming off try-hard in proving it. A strong good guy who decides to be supportive on his own terms, not a weak one.
Just then, her son showed up, and she introduced us. She said "I bet a lot more women have this issue than you think. I bet 9 of 10 women, if you ask them, have had the problem of being too nice and clingy to a guy they really like. How about you ask 4 women in this mall, and I can even give you my room number, and you can tell me what they said. I talked for a bit more, then said "So what is your room number?" She turned and pointed to her floor of her apartment building and told me her room number. This was all in front of her son. I ended saying "Well I'm gonna get back to my friend now, but I'm glad I made you think." She said "You definitely did."
Now obviously, she couldn't show any real obvious IOIs in front of her son. I'm wondering what you guys think. My plan is to actually take her challenge, and use that same real life opener with at least 4 girls, before coming back to her place. I'll tell her that I took her challenge and talk about the results with her. I might bring a bottle of red wine in a backpack (so she doesn't see it until she's earned it), suggest we walk her dog, and leave my backpack at her place so I'll have to come back in to get it one way or the other.
So what do you guys think of my plan? I made a note of her name and her apartment number. I don't know when she works, when her son is with her, and whether he lives with her or just visits. What time would you recommend my stopping by? I first met her around maybe 9-10PM. Anything you'd tweak or advise?
she wants the D...
anyways I would honestly suggest an off day, Tuesday maybe? Better chances on them being home, or a Sunday, and around 7ish - just like how TV stations plan their shows, 7 o'clock or 8 o'clock are prime time, because the majority of people are home by then and are watching tv.
CHAT
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