I've been haunted by the times I didn't have sex. It was all for the best, but I could have had probably 3 times as much sex as I did in my earlier days if I didn't overthink everything.
Some highlights:
Had liked the girl for a long time and didn't want to rush in to sex, so I said we should wait. She took it as a rejection.
Was too hammered/high to realize that her showing up at my place at 2am and grabbing my crotch wasn't just her being goofy. She took it as a rejection.
All my friends, including her brother, said she was really bitchy and awful. We hung out every day and night for a month or so and had an absolute blast. She was one of the coolest, most interesting people I'd ever known. But I couldn't get my head around taking it to the next level, so we were "just friends" despite her best efforts. She gave up and became pretty bitchy and awful to me eventually. I guess she took it as a rejection.
She was drop dead gorgeous but a bit crazy and sexually adventurous. She used to come sleep at my house, in my bed, because I lived closer to work than she did. And she slept in the nude. I couldn't make the move though, so I became known to her as a "gentleman", which made it more of a challenge for her, which made it less appealing for me. She wasn't one to accept rejection, so this continued until I moved out of state.
She had cancer. I didn't want to seem like I was taking advantage. She was very sweet and probably wanted to forget about all the cancer shit and just connect and have a night of fun, but I made some excuse and didn't go. She died a short time later.
I'm hard of hearing. Had a HUUUUUGE crush on this girl but had been "friendzoned" hard for years. One night she was upset about something, and asked me to hold her in her bed. Yes, the old "just please hold me until i go to sleep" scenario. This was pretty unprecedented, but not entirely out of character, as we were best friends and she'd been getting more and more affectionate for a few months. After a while she stopped crying and leaned over and kissed me. Sort of a preliminary, very soft on the lips but no tongue kiss. This WAS unprecedented, and my adrenaline shot through the roof, to the point where you get that freight train sound in your ears. Then she said, "Just please don't......" but due to the freight train in my ears and the very quiet way she said it, I couldn't hear the last part. I mean, it could've been, "Just please don't LEAVE", or "Just please don't TAKE ADVANTAGE OF ME", or "Just please don't SAY NO", or...
I had no clue. So I just lay there for a bit with her looking at me. Finally I asked her what she said, and she said, "Please don't make me repeat it". So I just lay there. After a while, she got angry and told me I'd better leave. I still have no idea.
And finally, this one stings the worst. She'd been a girl I put on a pedestal and worshiped earlier in life, but knew I'd never have a chance. Fate had put us on intersecting paths again years later. There was a spark between us like the biggest bolt of lightning you could imagine. It was palpable. It was undeniable. She was all I could think about.
But we were both married.
We tried being just friends but it felt like holding my breath. While on fire. On a roller coaster. During an earthquake.
So we parted ways.