What a great topic for me...I have tons of regrets. The worst, I think, is when I didn't even realize I had a chance at something I wanted until it was too late.
I was at a party in HS and this guy from the wrestling team asked to go in the bathroom with me. I knew guys would do that at parties though never really understood why. I should have known, I mean I was looking at The Joy of Gay Sex in the bookstore at every opportunity. I said "sure," but was nervous because I thought I had a small dick and was ashamed and also nervous about being found out to be gay. I pissed first, I have no idea whether he was looking or not, but when he went I kept my head down so there was no chance of seeing anything. We left and that was that. Years later I thought "wait ...was he trying to get me to blow him or something?" That would have been a dream, and gotten me started on the road to sluttiness a couple of years earlier.
Another time I had been at the late great ABS on Rt. 1 & 9 and I was cruising this hot guy, not tall, but dark and handsome. We were both looking at each other, but he wasn't going back where the booths were which was what I expected him to do if he wanted to fool around. He then started to leave the store and I followed. I was so confused when, although he waited for me to get outside, he went into his van. I waited for him to get out, or come back, or leave, or something but nothing happened. I was so disappointed that I just wanted to go home. As I got home it hit me that he probably wanted me to get in the van with him, "Stupid, stupid, stupid."
I am happy to report that I have wised up some, but this is just a sample of my many missed opportunities. Read them and learn...who am I kidding, no one else is this dense.