Oh, man. I've got a couple, but one of them might have to be my first night in college. I'm not sure I'd classify this as a date, and I'm the one who made it weird. My college roommate was an acquaintance from high school - we'll call him Lucas. Lucas and I went to a party we got invited to from one of the older kids in the dorm and we were excited, it being our first night staying in college and all. We drank a little vodka he had brought to kill the nerves before the party and proceeded to walk to the house. Everything was pretty close by, so it was only a mile or two and we didn't want to sacrifice our parking spots just to drive home drunk. Before we got off campus, two pseudo-cute girls (we'll call them Janet and Bridget) invited us to another party. We looked at each other and instantly knew this is what we were doing instead. We had to stop by their dorm first and then we'd be on our way. This is where things start to get spicy. They snuck us into their dorm, which was women's only, and we sat down to watch whatever was on the tv while we waited for Bridget to use the community restroom down the hall. These dorms are tiny, so I was sitting with Janet on a twin bed and Lucas was across from us on the other twin bed ~3ft away. Janet proceeds to make out with me and I go with it because I never got this attention in HS and I'm learning to love college. Idgaf that Lucas is in an awkward situation. Lucas lays back and starts watching the cartoons, pretending it isn't super uncomfortable for him. That's when Bridget shows back up and sits on the bed with me and Janet, who's getting finger diddled under the sheets (we were horizontal). Gets a bit hazy from here, but at some point I ended up with Bridget on top of me having sex while Janet continues to make out with me. Sensory overload - I completely forget about Lucas. I have no idea what I'm doing - this is only the 2nd girl I've ever slept with, but all I can think about is her crotch stubble is shredding my groin like a cheese grater. I pretend to finish, I get up, walk to a women's only community restroom and start to pee. I never bothered to put pants on, so I'm standing in a shirt & no pants, pissing in the shower drain. Or so I thought... The condom was still on and filling fast. It was about that time a girl walks in and the condom, full of beer pee, falls off my pecker and explodes all over our feet. We make eye contact - she's in horror, and I run back to the room, jump into my pants, don't even acknowledge girl#1&2 and start jogging back to the dorm before I get an infraction for the numerous rules I broke on my first night. Poor old Lucas had been waiting the. entire. time. He was not pleased and showed up to our room about 5 minutes after this fiasco and called me an asshole. Never saw the girls again.
TL;DR - Got invited to a party with college roommate, went to girl's dorm instead, awkward threesome-ish thing happened while Lucas apparently watched, and then I accidentally got pee on some random girl and went home to an angry Lucas.