Short story:
So as the title says I like this one girl. Like a lot. I've known her since we were both 5 (we're now in our 20s) and I've always liked the thought of dating her, but I never was very confident. Now, after reconnecting, I've asked her out (to which the answer was yes, but was "rainchecked"), but I can't tell if she's just trying to be polite and not say no directly. I also suspect she may just like the attention I give her as she is very attractive (definitely a type of girl that under normal circumstances I wouldn't bother chasing after).
Long story:
Basically this girl has been in my life for a long time. I wasn't exactly close with her through most of high school and college, but we were always friendly with each other and catch up randomly.
Recently we've begun talking again, and I have a lot more confidence now then I did before and things have obviously gotten more than friendly. At least for me. We're very different people seeing as I've only dated two girls ever and would classify myself as introverted, whereas she's had many relationships and she's definitely more outgoing. But we do get along, partially because of our long history.
We've talked a bit in the past two or three weeks, mostly texts and snapchats, and some of the conversations are innocent (e.g. "how's your day") and others are more flirtatious (she's sent me a few pictures of her in her bra, etc.) Normally, I'd expect that the latter type of conversations would mean she's interested in me, but I've always known her to like getting noticed for how attractive she is.
We've gotten together once since we started talking to each other again and caught up, and it was a very good time. We talked about going on a date, set up a day, and then she cancelled because her job came up. That's fine. But she's kinda skirted the issue since. We still talk randomly, both typical day to day conversation and more racy things, but I'm not really interested in just getting pictures and giving her attention.
I'm not a huge fan of chasing girls, nor am I very good at it. I also haven't looked into dating a girl for a long time and this is the first time I've actually been interested in about two years. Is there something here, or is she just looking for attention? If there is, any suggestions on how to actually get things started? Right now I'm trapped in a power struggle and that makes me feel like I'm back in high school.