Worst first dates end up being the best stories you share with your last date (your spouse). It’s like telling personal injury stories where everyone tries to out gross each other with tales of botched emergency room visits.
My worst was in college. I was a freshmen at Westmont, a small school where you couldn’t have a car until junior year. That alone made it hard to even get a date. Not to mention that all of these pretty girls were like, “I’ve pledged to not date for a year!” But they lifted the ban whenever an upperclassman with a set of wheels showed them the briefest amount of attention. So I was proud to have even secured this date. But not having a car meant we had to take the school shuttle.
In hindsight, the shuttle was a nice luxury afforded to the carless. It made six stops around Santa Barbara before returning to school. At the time though, we dubbed it “the shame shuttle.” So I take my date out in that. Classy. One step below sixth grade dating, where at least your mom could drop you off unaccompanied to hang out at the county fair with a girl and endure the tilt-a-whirl just so you could accidentally touch hands for a second. But on the shuttle, you got to take your date on a ride with eight other people who all knew you were on a date.
You can’t make awesome first date small talk surrounded by peers who are pretending not to eavesdrop. Thankfully, we were headed to the first stop, and only had to endure ten minutes of awkward. For a bad first date, that meant we had many minutes of awkward left to go.
How did I even get this date? Our dorm had organized what was called a NCTO (nick-toe), meaning “noncommittal takeout.” This was the PC name for what had once been called “screw-your-roommate,” where your floor goes on a group date, and your roommate has to secure your date. The “screw” in the previous name meant you could screw your roomie over by getting him a terrible date, hence the name change to be more appropriate. In reality, we all called it NCMO (nick-mo), which stood for “noncommittal make out,” although I know for a fact that this did not happen to me or any of my other friends.
This was also pre-Facebook or MySpace, yet our school was advanced in the arts of invading digital privacy. We had the unfortunately nicknamed “StalkerNet,” originally called the “online student registry” before the creepy moniker stuck. It had your photo, room number, home address, and home phone. Way too much info. And asking out a girl for your roommate generally went like this, Her: “Oh . . . let me check my schedule . . . <pulls up StalkerNet, notices your roommate is good looking> . . . No papers due that week, I can make it!”
You also had to decide if you wanted your roommate to ask out a girl that was a friend, or a girl you actually liked. The fate of your entire bowling adventure or capture the flag game on the beach was on the line. I opted to take friends so I could make fun of the guys who were trying to impress their dates. It was extreme people watching, a worst first date en masse: 20 guys having a horrible time with girls they liked, and 20 guys actually having laid back fun.
I was always the latter, until I broke my own rule. I thought I could beat the system by preempting our first date with a first date, so that the second one wouldn’t be painful. And by painful I mean a fifties bop theme at a roller rink, where I tried horribly to look like the Fonz, and no one took good pictures of each other.
Asking her out went normally. “Hey, let’s go to Starbucks the week before! It’d be fun to hang out.” “Sounds good.” Skip to us getting off of the shuttle after lots of head nodding and polite conversation. We’re in line and I say I love coffee because that line was supposed to work on girls and she says she doesn’t really like coffee very much. Okay. Ummm. What do you want? Tea? No, I’ll just have a hot water.
I convince her to order a hot chocolate, because I was not about to buy my drink and then get hers for free. We sit down and start talking, but I can’t figure out if she’s shy or just doesn’t like me. After an hour, I find out a startling fact. Her family has a town named after them in a Scandinavian country. Like named after them on purpose because they owned a giant factory in that region. Also, she hasn’t really gone out on many dates. Or had a boyfriend. I was confused because she was very nice and pretty and at my high school she would’ve been asked out a lot.
The conversation petered out after an hour and she didn’t finish her hot chocolate. The ride back on the shuttle was a quiet one for us. But the other eight people riding with us were laughing and having a good time. Quite in contrast to the “okay” time we were having.
The group roller rink date didn’t shine either, so of course I asked her to the winter formal. Yep, we had those, in college. And that was also “okay.” Then I realized I was trying too hard and she was just being nice. After Thanksgiving break I stopped trying. We were simply destined to fulfill the noncommittal part of the NCTO.
Okay, the setup was better than the actual story. I like to disappoint you in that way. Tangentially take you by the hand, until you say, “Wait, that’s it? That’s not even a bad date.” To make up for that, I asked my friends to tell me their worst first dates, and apparently they are a deep well of misfortune, because they came up with some great and terrible stuff I will share with you soon.