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.

>Give her a text saying I had fun and we should hang again. No response.

Maybe you do need to be a little clearer and suggest something different. If you've sent one text and received no reply, there's not a lot of meaning you can get from that because it's quite minor. Basically, don't worry about that too much.

If you called her and asked her out to dinner, or some sort of event, I'm sure that'd be lovely and nice and direct.

>>2835
>If you've sent one text and received no reply, there's not a lot of meaning you can get from that because it's quite minor.
Actually, there is a lot of meaning he could potentially take from that. It could mean she felt uncomfortable during/after their previous get-together, knows he's interested in her, and doesn't know how to turn him down. Obviously one not-returned text is nothing conclusive, which is why he should send another text and let her know he's interested in getting together again. If a second text isn't returned, that's a pretty solid sign she's avoiding talking to you, OP, as immature as that is on her end.

>If you called her and asked her out to dinner, or some sort of event, I'm sure that'd be lovely and nice and direct.
At this point, calling her and asking her out to dinner would be misguided. Send her another text, suggest meeting up for drinks or something similarly low-key and be more direct about your intentions in person, not over the phone.

A girl doesn't return his texts and the "lovely and direct" solution is to call her and ask her out to a romantic evening-long dinner date? If she's not returning texts, and was uncomfortable with an after-drinks hug, then that is coming on way too strong. That's like jumping from A to D, and skipping B and C. Text again, see if she's interested in hanging out again, and take things from there.

yay Uriah Heep

Alright guys so I ended up getting a text back from her. She apologized for how long it took and said she had a fun time too. I actually ran into her again later at a bar. Things weren't very awkward at all. We each complimented each other, chatted, and went our respective ways. We were both busy.

I think she may be interested but is sort of testing the waters. I talked to a couple of my female friends and the consensus was to wait a a week or until I run into her again, give her space, and then ask her out on a more direct date. Like to dinner or something. I'm pretty sure I'll stick with this plan. Thanks for all the help so far. You guys know what you're doing.