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No. 2831
I would say the most important thing is to be clear from the get-go. When you asked her out for drinks, were you thinking/hoping it would be a date? If yes, why didn't you make that clear to her at the very beginning? If no, why not since you clearly are interested in something more than platonic with her. Honesty is important, both with her and with yourself. Are you interested in taking her out on a date date? Then be clear about that.
>Like I'm talking some of the best conversation I've had. We're joking around having fun.
Fun, relaxed conversation is great, but it doesn't automatically show or lead to mutual attraction. Just because conversation comes easily and is enjoyable doesn't necessarily mean you're flirting.
I imagine that the awkwardness with the number exchange/hug at the end of the night was probably the result of her realizing, as time went on, that this meet-up for drinks and chatting carried more expectation on your side than just two platonic buddies hangin' out.
>I'm really bad at escalating a night past friendship.
Escalating past friendship isn't something you do at the end of the night. It's not really something you "do" at all, it's not a move. That's not to say you shouldn't take initiative on escalating the relationship, by all means you should. But it's something you need to be clear about and get the ball rolling on very early. Ideally, make it clear when you ask her out for drinks that you are asking her out because you are attracted to her and want to spend some one-on-one time together. During the date, like I said, good conversation is one thing but it's not necessarily the same as flirting, playing, creating sexual tension, etc etc. Escalating past friendship isn't something you make happen at the end of the night. It's something that grows over the course of the date(s).
The key here is respect - both for her and for yourself - by being clear and honest about your intentions and having fun while doing it. Reading over this post, I'm making asking someone out sound like a dry, serious endeavour where you put on your most grim facial expression and recite an itemized list of your expectations. It's not. Be lighthearted, have fun. Really that should be your main focus. But make sure that she understands it's a date and that you like her. This doesn't involve cornering her and confessing your feelings or anything, but it means being clear about your attraction to her and your desire to pursue that more, if she is interested too.
Have fun but be clear too. It's actually not that much different from what you're doing now.
As for how you proceed from here, I don't know. The lack of response to your other text sucks and is pretty immature in my view, but also understandable; these awkward little situations can be difficult on both sides. Shoot her another text, saying you had fun and would like to see her again, see how that goes.
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