I have three. These make me sick to my stomach. I have never been very good with social situations, but these take the cake for "what the fuck was I thinking":
1) When I was in middle school, I had left a fourm I needed in a previous class. I asked for permission to head back and grab it. I went to my seat and ask the girl there if she had seen it. "Oh you mean this, anon?" And she proceeds to play keep away with it, handing it to me then pulling away at the last minute. I think she was flirting with me, but clearly I didn't get it because I cussed her out, grabbed it out of her hand and as I turned to leave let a huge fart rip right in her face. I got suspended, which means I couldn't go on the school trip. When the dean told me, I totally cried bitterly like a little bitch in his office.
2) Highschool. Had a crazy Armenian freind. He was a psycho, gave zero fucks. Called a thug-ass black kid a "Ni**er". No joke, to his face. Kid followed him into the classroom and threatened to fuck him up. Freind was dead cool, told him to do it. Teacher told the black kid to leave, placing a hand on his shoulder. Kid threw her hand off aggressively and yelled he didn't give a fuck. Me, being retarted, thought this might devolve into some Columbine, kill everyone in the class bullshit (because all black people have guns, right?). So I hid under the desk in the computer lab and placed my backpack in front of me. After the black kid left, a super hot black girl in my class noticed what I was doing and call me out for it, laughing with pitty. Thank God she wasn't to mean about it. I said I dropped my pencil, but she knew exactly what was going on.
3) College. Had a super hot black girlfriend. She's at a freinds house getting shit faced and I start getting hot texts. Says she'd totally let me try dp on her with a dildo if I was there but says her freind doesn't want me to come. I go full retard. I somehow convince my poor, loyal, amazing best freind to come along. We hop the fence to the gated community, show up at the door. My freind is rightly stressing the fuck out; he knows this is soooo wrong. I knock, they openx the door. I'm holding a bag of dildos, at the door to my GFs freinds house, her freind just stares at me in horror. We leave.
Phhhhhew. These all make me want to curl up and die with same. Hopefully I'm not this bad anymore... fuck.
I look back on the way I used to act and it's so disturbing that this was me at one point in my life. All I can do is try to learn from these mistakes and move forwards.