So, as fate would have it, I end up with a friend at a coffeeshop around 10 [they close at 11]. Before this point, I had never had an approach go past flakey numbers. There's a cute asian girl, (an 8 if you must) sitting alone - I tell my friend half-jokingly 'I really should go talk to her'. He says 'you know what you should do'. I had already thought about it too much, usually I do best with the 3 second rule, so I didn't.
Me and my friend are chatting, and he says 'hey, she's leaving, now's your chance' (kinda jokingly). She walked past us, out the door - I said 'yeah, one sec' and went outside. This was an easy approach, my big problem is other people in the area if I'm going direct. She was near her car.
'Hey, I don't mean to stalk you in the parking lot, but I thought you were cute and I had to say hi. Hi, I'm ___'. She was curious - 'Hi, thanks'... (i forget the details, I probably said 'how are you doing?' and went from there). Soon after, she said 'do you want to sit in the coffee shop?' - 'yeah, sure!'. And so we had a 30+ minute convo - to be honest her response to my approach threw me off a bit, she was so chill and accepting - internally I wasn't at the top of my game for the first half of the convo, but became more at ease as it went on. It was about to close and I suggested we hang out soon, phone trade, etc.
It turns out she was traveling in a few days, so I suggested we meet the next day - she agreed.
================= Fr#2
A note, at this point - I'm a decent looking guy at times, I'm usually pretty good at initial casual friendly/funny banter, but am still figuring out how to best handle 'dates'. In a night-club setting, I don't have many issues being more direct / kino / etc, but have little experience handling daytime / date escalation.
So, we text a bit, she needs to postpone our meeting till that night, but it wasn't a flake (which I was worried about). We meet, found the pool hall closed and decided to go to a pub. I had 2 drinks, she had 1, we talked (and it got pretty deep - I suggest getting this sort of convo going as soon as you have enough comfort established, it really helps you two learn about each other non-superficially).
Bla bla bla, it got late, I drove us back to her car in a parking lot, we chilled for a bit, walked her to her car - I got the vibe she was interested, but throughout the night didn't get any clear 'IOI's or overt flirting, so I wasn't certain she was up for kissing (note that she is foreign, has been here a few years, but was raised in a more 'proper' culture). I had been doing some minor kino throughout the night (but it still needs work). I start to invade her space a little, but she turns away, I figure that tells me she is not up for the kiss. We hug, say bye, and I say fuck it, I'm going for a kiss on the cheek, so as I'm nearly a step away, I turn and move in to kiss her on the cheek, she turns and I find us somehow making out. Woah, talk about unexpected. We make out for 10 minutes or so, I press her up against her car, she starts some 'over the pants' action. At this point, I realize it is in fact worth it to approach a girl even if you're not entirely sure about it.
For various reasons, mostly little sleep the night before and drinking, I was in no good state to suggest we go back to either of our places. I tell her she's coming over tomorrow, she says 'I won't have time until 9, is that too late?', 'That's fine'.
She texted me the next day and said she didn't want to be in that sort of situation right before she was about to leave for a month or two - that's fine, so far she seems pretty level-headed and hadn't played any games with me. There's a few more details on our texting back and forth after this, but that's the main story. If I was solely interested in getting laid, I could have tried harder for that, but she is actually pretty awesome compared to others I've recently met so I'm content with where we're at (though you better believe now that we have gone that far, I'll be pretty direct the next time we meet).
Lessons:
Approach if you feel there is even the slightest chance she'll be interested.
Don't be afraid to go for the kiss after enough 'obvious date' time has passed.
Whether it works out or not, I'm starting to realize I'm not, and I shouldn't be upset if it doesn't. When she's back there's a chance we'll continue where we left off.
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