So many, but the biggest and most cringe worthy is probably not making a move on my sister's hot friend. In high school I was more or less the alpha nerd (if that's a thing) and threw big LAN parties every month or so. It started off as just dudes, but eventually some of my chick friends would attend too. In one of my last LAN parties of senior year one of my sister's hot friends showed up and she and I instantly hit it off. Towards the middle of the night I had said "fuck it" to gaming all together and was just hanging out with her on the couch watching movies (if I recall, the specific movie was The Last Unicorn). We were sharing a blanket and eventually hands began to roam. I had my hand in her pants UNDER the panties when one of my friends busted into the room shouting my name. My hands flung into the air like I had been caught stealing and I shouted "HI ALEX!" as if that would convince him that nothing was happening. To this day, I'm not sure why I did that. Needless to say, the mood kinda died down after that. We hugged and she went home and I thought that was the end of that.

A few days later this chick was back over and we were hanging out in my room. We started talking about porn and what kind of things we were into. This was around the time that the movie 40 days and 40 nights came out, so for some reason we decided to make a pact to not masturbate for 40 days. Over the next couple of days she would admit to me every fucking time she masturbated, and would talk about it in detail. She even made the stipulation that technically it isn't masturbating if someone else is getting you off instead. She was practically saying "fuck me," but in my retarded virgin mind I heard victory bells as I was winning the fuck out of this challenge. Needless to say, I eventually won that challenge, but the only prize was a couple of blue balls.