Many. This will seem like humblebragging or something, but I feel like a fucking retard. Like, these are all burned into my memory now as things that I feel really stupid and awful about... I just have traditionally had really awful self-esteem and tend to just push everyone away with disbelief when they show an ounce of interest in me.
Some were pretty obvious. Like when a really sweet and pretty girl I liked in middle school straight up asked me out and I thought she was just fucking with me, so I got annoyed and said no. She wasn't fucking with me :(
This similar thing happened lots of times in grade school actually. Asked out, said no out of disbelief.
Cute kinda trashy chick in middle school rubbed herself against me and tried to get me to... I don't know at this point, but it probably would've been fun. Looking back on it she was probably abused or something so it probably was better not to do anything. By high school she was being kind of passed around by a lot of guys.
Cute goth chick in high school tried to come on to me. I brushed it off.
Close female friend in high school apparently was in love with me and I pushed her away and ended up dating someone else. I really wasn't attracted to her, but I really cared about her... She turned out to be gay in the end though, so I feel like I really just helped accelerate her self-discovery. That's the positive spin anyway.
Another "lesbian" in high school who was in a committed relationship with another girl decided she wasn't really lesbian anymore and apparently was coming onto me, which I didn't find out until later when she told her partner and her partner gave me a ton of shit about it. Not sure how much was her being into me and how much of it was her trying to sabotage her failing relationship.
A girl in high school was really into me and I had built a relationship with her through school projects, stuff in common, etc. She was smart and cute and everything, but I only realized too late that she was actually waiting for me to actually ask her out.
A year or so ago a cute chick checking out at a Goodwill asked me if I wanted to go to dinner and at first I thought she said something else so I just kind've chuckled and left. Parsed what she said afterward and, well, I'm married now so I'm probably not going out to eat with random women, but I felt like an ass for my reaction.
I DID find someone, obviously, because I'm married, but it was only through sheer force of will and persistence that she managed to break through my thickheadedness. I'm in my early 30s now so most of those were a long time ago. Now I intentionally don't shave or get haircuts very often, just to be safe. I also often maintain a male "resting bitch face". The thing is, I'm not that attractive. I've always been a poor scrub with no social skills. I don't know why anyone has ever shown me any attention. I hate attention most of the time. I just want to be left alone by most people most of the time. Fuck.