| Hey all, had my first pickup recently that seemed to be going pretty well, but then it took a very strange turn on me.
Day 1 - I am out with my best friend/wing on Saturday night, and suddenly being in the mood to sing we make our way to a bar near his place that has karaoke going on. Place was rather dead, but we start having some drinks and attempt to liven the place up. We're just having some fun at this point as the selection of women is super thin/non-existant. My wing goes to the connecting bar next door to try and recruit some people to the cause. He comes back with a MFF 3-set. I introduce myself to all of them and my friend leaves.
I manage to isolate my target in conversation, it seemed important she let me know the guy was just a friend lol. They were all drinking and naturally being touchy and what not. Then she tells me she remembers me from a different bar a while back but we were both with people, though also mentions that he was also only a friend. I make a remark about men and women not really being able to be friends that someone almost always wants more. Then I told her, honestly I think you're cute, to which she said when I first saw you I thought you were cute but you were with that girl. We talk more, dance for a little bit, exchange numbers and that's it for tonight. Relevant info about her is I find out towards the end of the interaction she's 34. I'm 27.
Day 2 (Sun) - her phone was dead Sat night, so I wanted to make sure I got a text in while I was still fresh in her mind. We banter a bit, I find out she's free on Tuesdays, she says she's glad she saw me again.
Day 3 (Tues) - I text her towards the end of work, she's being more flirty with her messages, I suggest meeting up later on. At this point she tells me she wants to let me know she has a son, she's still up for hanging out, and not that she's looking for anything serious, but she felt weird not letting me know. I tell her it's cool I appreciate her telling me, and that I'm still interested in meeting up. She remarks about wishing there was somewhere having karaoke tonight. I ask my wing if there was, he comes up empty, but to let him know if I found one. I have an epiphany that there is in fact a bar doing karaoke about 5 mins from my house! The stars seem to be aligning on this one. I tell the girl I'll pick her up at 930.
We arrive, place is slow at first, but we get to sit at the bar and chat a bit, I'm doing a little kino, trying to slowly escalate and set a sexual frame while we have our first drinks. She reciprocates and tells me she's nervous and that I'm cute. My friend shows up and is hanging out with us. The place starts picking up with lots of young attractive women and a favorable ratio (I know where we will be next week! haha). I leave to use the restroom, when I come back, I approach the girl from behind and put my hands over her eyes. After she turns around we are standing pretty close, and I kiss her. We start kissing a little and then go back to sitting at the bar. She goes out for a smoke and tells me as she's getting up "I'm really glad you kissed me". I take her to a quieter corner of the bar when she gets back and make out for a bit. I go outside with her a little later and kiss her neck and make out with her some more. (This is the point I should've bounced out) She tells me she's usually never like this (in terms of having a guy touch her, or making out like this in public). I take this as her giving plausible deniability? (am i even using this term correctly lol?) We go back inside, I get called up to sing a song, her and my friend are chatting at the table.
My plan at this point is to try and escalate again, and when things start heating up, leave and try to get her back to my place. We start to dance a little bit, and then she goes to the bathroom. Here's where things get weird. She comes back not looking too happy and says I want to go home. We leave, and I'm trying to figure out what sparked this change. She says my friend told her that I'm a nice guy, but that I'm a player, that I'm not looking for anything serious. Then she goes into how she's really attracted to me, she's a passionate person, etc., but that I should go mess around with beautiful 27 yr old women, that she doesn't want to waste my time. She apparently has the mindset that she's not worthy of my time or pretty enough for me. I remained cool even facing the possibility that my friend back-stabbed me (he was drinking so you never know right?). I told her that I'm a straight shooter and my thoughts on dating (basically to approach every situation with an open mind that it can either be short or long term and to not be "looking" for one or the other). I feel like this was consistent with my direct approach on day 1 (Mode 1 style). I also told her, that I would honestly be disappointed if something someone else said, got in the way of what we had going on. As I got to her place she was almost to the point of breaking into tears, as she's really into me, but I can tell she's been through some rough experiences in the past.
So if you made it this far.. thank you! I definitely have a tendency to be thorough and long winded. How do I proceed in this situation? I feel like either her low self concept will overwhelm her and convince her not to see me again, or her attraction will win over and she will. I'd obviously like to induce the latter if possible. If I can somehow get another meeting out of this, I sure as hell am not telling my friend where I'm gonna be!
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CHAT
Take her out again and work on building some comfort. Maybe something not drinking related, and not at night, so she won't be in full defense mode? Good luck bro.