This happened a few years ago, I had had been out of college for one year and I was at a very low point sexually. I was still super hung up on my college ex and was having severe ED/PE problems. I was trying /r/nofap to ease my issues and hadn't watched porn or jerked off in a few months (this comes in to play later).
I went out to NYC to visit some old school friends for a week, and asked my friend Rae if I could crash at her place. She and I had fooled around casually on and off through school, but were mainly friends. This woman is an absolute stunner American dream Barbie doll porn star hippie love queen though, so I figured the chances of her having a bf (and therefore being off limits for me), were high.
Anyway we hang out that night, have some drinks with some friends, and have a great time. I'm feeling comfortable and like myself for the first time in a while. Everyone's laughing and I figure I'll just play it cool and see what happens, and that even if nothing goes down I'll be happy. No boyfriend in sight though.