So, I had a big crush on this girl, which I'd had for the years I'd known her. She was the quintessential popular girl: usually judged the prettiest in the school, the smartest, and did all the extra stuff. She was also really sweet. Anyway, being the kid with the massive balls, I'd asked her out pretty much immediately on meeting her. She said yes, but before we actually had the chance to go out one of her friends said she didn't find me attractive but figured I was funny and nice anyway, so she'd give it a go. Naturally, being the idiot macho kid I was, I said fuck it and told her there wasn't any point in us going out.

Fast forward a few years. I've always found it easy to talk to women: I grew up as the only guy with three older sisters and a dad who wasn't really around. It was really female dominated and they're all really ballsy, so I grew up not finding women intimidating. This is important, because unlike pretty much all of my peers, I was able to maintain ordinary supportive friendships with women. So, this girl and I were friendly: not close, but I'd helped her through some really rough spots that she couldn't tell anyone else about. I guess I was just the 'real' one that she knew she could count on to be serious and trustworthy and not intimidated when she needed it. So, there's a huge group of us just hanging around, and someone says to me that she has a crush on me and wants to ask me out.

In that moment my brain didn't consider that this might actually be true. So I acted with what I thought was chivalry. Knowing that I was very far from cool and that sort of rumour would make her look uncool, I said 'lol, don't be ridiculous, she doesn't have a thing for me. We went out years ago and she dumped me' (this lie was meant to make her save face). The crowd literally parted while I said this and I saw her face drop. She took this as a very public and humiliating turn-down... In reality it was me not considering that she might actually like me, combined with a genuine attempt at chivalry. So, yeah, she fucked off and got together with a series of scummy guys one of whom got her pregnant and pretty much stomped all over her dreams. Lovely mother though. :-/