Most Helpful Guy
Back in high school it happened. It's a story I've told countless times on here because there was so much potential win in this situation that I kick myself for now.
Firstly, the girl was just the closest thing to a perfect 10 that I've ever seen. She is Colombian and is responsible for my preference of Latina girls to this day. When I say preference, I don't mean all or nothing but more of a bias kind of thing. But anyway, I had 2 classes with her freshman year. In one of them, she was kind of quiet around/towards me but she still found reasons to talk to me even if it was just little things like where we had to turn a paper in at.
Over time, we eventually got to talk more and more, got more comfortable with each other, that whole bit. We ended up getting sit by each other in one of my other classes and we talked a lot in class about just anything. She started flirting with me- fun flirts, "dropping hints" kind of flirts, sexual flirts, the whole story. I was terrified of this girl even though I was comfortable as friends with her. I not only felt "below her league", but I was scared because I didn't know how to proceed, nor felt comfortable because I had never tried anything with a girl before.
Eventually I think I gave her no choice but to move on from me and date other guys (the typical jerks I might add). I felt relieved because I didn't have to worry about trying to figure out how to get with her, but felt really down because I basically sabotaged myself. I could've had a great girl, and I could've saved her from going for the jerks lol.
But oh well, it's done and over with. So to answer your question, yes it has happened. Not sure how often it would happen in life but it has happened to me before a couple of times, but that's the one I remember and think about the most :/