The only really bad first date I've ever had was an absolute disaster. I came in from my freshman year of college one weekend, and the girl babysitting my sister (let's call her Jane) was pretty cute. She was a senior in high school, we got to talking a bit, and I ended up getting her number. We talked once or twice on the phone, and she ends up asking me to her senior prom. I felt a bit weird going since I didn't know a single other person at her school, but I also knew I was going to need a good study break that weekend, so I decided to go and blow off some steam. I really should have trusted my instinct. She tells me we're supposed to go out for dinner with a group of people, so obviously I held off of eating. Well an hour and a half after she was supposed to pick me up, I'm about to pack my stuff and head back to my dorm when she shows up with a friend (let's call her Tammy, a good white trash stripper name). She tells me she's sorry they're late and that they already ate, so we could just head straight to the dance. I was starving by that point, so I said I needed to get a quick bite before we went and tried tried to convince them to just let me run grab some fast food, but they insisted we go to a "fancy restaurant." We end up at Chile's, and I feel like a complete jackass eating by myself while these two girls watched. I was trying to be a good sport and do what they wanted for the sake of the night, which in retrospect should have ended when they were late. The conversations were awkward, and most of the meal consisted of Tammy hitting on our waiter. I then find out that not only did Tammy not have a date, she didn't even go to the same damn school. It brought me to ask the awkward but inevitable question, "What are you doing here?" Jane said she wanted her best friend with her on her prom night. If it wasn't a certainty before, I knew for sure the rest of the night was going to be awful.
I was pissed, but I played along, thinking maybe it would pay off in the end. Before we head to the dance, we stop by Tammy's house because--despite being comfortably dressed and in public for over an hour--she didn't like the way her outfit looked. I agreed that it looked horrendous but kept my silence. We get inside, and they run into a room to try on dresses. I didn't even know where to sit because this house was fucking filthy. There was pet hair coating every piece of furniture, and I felt like I just snorted a few lines of high grade pollen. So Tammy's weirdo mom comes to keep me company for at least 30 minutes. This whack job started introducing me to all her pets--the most noteworthy being George Harrison Gerbil and Ringo Rabbit--using what she felt were cute voices for each intro. I was ready to bolt, but the girls come out the room. Tammy was dressed like a cheap hooker, but I didn't feel the need to say anything since I finally had a good excuse to get the holy hell away from that animal house.
Well we get to the dance, and apparently the school doesn't let girls wear dresses that cover less than a bathing suit, so we aren't allowed in--and by we, I mean Tammy only. Back to the funny farm we go. As they go back to change, her dad arrives home with Tammy's little 6th grade sister, who had just been caught fucking her boyfriend at his parents' house. I get to listen to a guy with a handlebar mustache, pony tail, cheap homemade tattoos, and a voice like Lou from Major League berate this little escort-in-training right in front of me. At this point I started working on a ride home, as I felt I was about to be a first hand witness to child abuse. I wasn't having much luck, and Jane and Tammy walk outside and found me hiding on the porch. Tammy is wearing the same fucking dress!!! I couldn't believe my eyes. They seem to think security would be wearing thin by this point in the night, so Tammy would be able to walk right in. I politely broke my silence and told her she needed to go find something that covered both her stomach and the lower half of her tits before we left because I wasn't making another trip back there. 4 phone calls with no luck later, and the girls are *finally* ready to leave.
I'm in the backseat of the car--debating whether I even wanted to wear a seat belt--when Jane sees her ex-boyfriend driving by. Of course she does. "Let's follow him!" I thought I was on a fucking hidden camera show. I'd only dated normal girls before (and after); so I couldn't believe this was reality. Anyways, the ex figures out who's behind him, and he takes off (presumably for dear life), only for Jane to stick her head out the window and drop a few swears and threats at the car as it sped off. Now the pre-party festivities were finally over, and it was time for the prom, which is maybe an hour and a half from ending.
We get back to the dance, and Tammy is up to code. We are maybe five steps through the door when Jane screams "OOOOOOH MYYYYYY GOD!!!" while running in place. I was embarrassed and even felt bad for her, which really says something given the misery she'd been dragging me through. She and Tammy darted off to a crowd of their friends, leaving me standing behind. The dance was only 3.5 miles from my parents' house, so at that point the walk was well worth it. I took straight to the street and was finally able to work out a ride home about a mile into my escape. I packed my bags and decided to drive home that night. I end up with a voice mail later saying, "I'm not sure why you ditched me on my prom night, but we're going to a party and I really want you to come, so pleeeease call me back!!!" She called maybe 4 or 5 times over the next week, but I had no intention of ever picking up the phone. I've never heard from her again, but I can only assume she now works the desk at a tanning salon during the day and waitresses at strip joints in the evenings. Tammy more than likely contracted HIV and was beaten dead by her pimp.
No Cliffs, spent too much time typing already.