Wow, I just skimmed the first 12 or so pages of this thread, I wish I could give Toad a hug :/
Anyway, I'm one of those guys that doesn't have too many encounters, that's what makes the times I do sweeter. The last one was a couple months ago, I met a neighbor's friend one night (long story short, I was getting ready for bed to get up early, they both swing by pretty tipsy, I decide to go out with them for a bit) and got her number. After texting for about a week, I met her for hookah. I didn't think it was going anywhere: she wasn't talking a ton (anxiety apparently), not flirting in a way that social morons such as myself can pick up on, wouldn't let me pay for her hookah, etc.
Afterward, she agreed to go get some food, but rather than agree to eat there like I proposed, she said we could go back to her place if I wanted. I guess I was wrong about her interest haha. By some cosmic miracle, I had a Netflix movie in my car, so we ended up eating while watching it, then she went to bathroom a bit. To keep it short, I resolved to make a move, consequences be damned, she came out in an skimpy tank top (essentially making my choice for me), said move worked, and I ended up getting to second base that night. I got greedy and tried weaselling my way to a bit more (a pretty bad habit of mine historically), but she just said "clothes on, at least tonight."
Afterward, she got all flaky, then eventually told me that she "just got out of a 3 year relationship." It was actually a legit line- talking to my neighbor, I found that she hadn't gotten over him at all whatsoever. I saw her again a few weeks later, and she didn't seem even remotely interested anymore (so much for the tonight line- gotta love false hope haha). Safe to say, time to move on.
The moral of this story is that even though nothing happened beyond that night, I still felt pretty damn good for a while after that. Why? Because I acted out of character by taking a chance in even setting up a date with a girl I had only met when she was a touch intoxicated, and again in making a move. I probably blew my longer term prospects by trying to move a bit too fast once I was in (figuratively ), but life is about messing up and doing your best to learn from it. In the end, it's a good thing I didn't get more involved with her, she turned out to be a submissive, slightly boring girl that would have driven me up a friggin' wall. Still, I look back on the whole thing fondly because it was fun at the moment, and I learned a lot from it.