Went out drinking with some friends one winter and decided to walk to my girlfriend's house from the bar. She lived with three other people in this older, two-story house. I banged on the door for God knows how long until she came down. When we got into bed, I couldn't stop singing Meatloaf songs (I was ripped, obviously). I woke up the entire house with my awesome music, as I learned the next morning. At any rate, I had dated this girl for 4.5 years and according to her, when she broke up with me two weeks later, it was that night singing Meatloaf songs where she realized that I would never grow up and she needed to end it.
I went down to the bar with a group of guys I really didn't know too well that were staying at our house for the weekend. They were friends with one of my roommates. I woke up the next day at 6:30 pm, missing all my classes. I didn't know what had happened in the previous 18 hours and I found that my wallet was completely devoid of cash. To the group of guys I went to the bar with, I was known as "Wild Turkey Man" for the next year or so. Apparently I had blown all my money on round after round of Wild Turkey shots and continued to puke the shots back up onto the dance floor. Which is odd, considering I've always detested Wild Turkey and dancing.
At a house party of ours I told a roommate's new girlfriend that she should be careful because he has herpies. It was the truth and I really hated the guy, but it was probably not the right thing to say even when you're trying to steal your roommate's new girlfriend.
Same roommate I didn't like. We were having a party and this roommate was completely out of control. My other two roommates and I decided to end his night for him so we challenged him that he couldn't bong 3 beers at once. He accepted and we filled up the bong with the three beers and about 6 shots worth of vodka. After he bonged it, I swear to God, he put on the same questioning face that Tyler Durden used when he shoots himself in the mouth in Fight Club, but instead of saying "What's that smell", my roommate said "Something wasn't right..." He was passed out inside of five minutes, pissed himself and never knew what happened. I'm still surprised he didn't die.
I was at a party with a friend of mine who would do literally any woman alive. This ugly little hippie chick was all over me and I really wasn't interested. So I told her that "if you really want laid tonight, why don't you talk to my friend over there." Interestingly, they ended up dating for like 6 months.
Probably the dumbest thing I've ever done is got a ride home from a friend of mine who was so drunk that he would fall asleep while we drove on the interstate and wake up and keep driving when we hit the rumble strips. That was a really, really fun night, but I still look back at that with horror.
The most bizarre is probably demanding a glass of milk to chase my shot of vodka. I quickly threw up both.