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A bit of background on her, she's a bartender. I texted her today saying, "Hey call me when you're free" haven't gotten a response yet.
Not really surprised by this. She came out on a day 2 with a guy that obviously she decided was worth a chance after (as you said) some rejections, and you didn't even attempt to kiss her? She's gonna be thinking one of two things or both, 1) I guess he just wants to be friends. Or 2) He didn't have the confidence to try and kiss me. My guess here it's the latter as you're clearly showing interest by asking her to call you when she's free, essentially saying that you're gonna wait around for her to call and she has all the control over what happens next.
My ex once told me that if I hadn't kissed her on the first date, we'd have never seen each other again because she'd have decided on those 2 points I mentioned above, we got into a discussion about it (like have her friends ever come across the same) and she said outright that ALL of her friends had been out with guys that didn't even attempt to kiss them, when in fact, even though they weren't even that interested initially, if the guy had the confidence to just say "fuck it" and go for it, they'd have not only reciprocated but even changed their opinion of said guy (she then cited a few examples of when it's happened to her and another friend).
To summarise, you played it safe and have wound up scratching your head wondering why you haven't got the second chance. Instead of taking the chance in the first place and potentially succeeding. If she was gonna kiss you, why wouldn't she do it there on that first date, as opposed to after a few days/weeks of texting? If she was ever gonna kiss you, it would've been then, sometimes if you can't tell whether or not she's ready, you just have to go for it and find out for sure. In my opinion though, if she's agreeing in an upbeat way to come to the top of a building with you, she must've liked you and that upbeat agreement right there should have been enough of a signal to say to you that she's interested enough to kiss you.
As for where to go from here, I wouldn't contact her for a few days to a week, if she re-opens then great, if not try one more re-opening (not asking her out) and if that bombs move on.