In honor of Valentine's Day -- the Official Holiday of Unmet Expectations -- we asked some of our writers to recount their very worst dates. Our hope is that these tales of failure will cushion the blow when whatever you have planned tonight goes horribly awry.
Back in college in the early aughts, I went on a couple dates with a friend of a friend. He was sort of an oddball, but I suppose that's why I was attracted to him. After we went back to his place, he interrupted our make-out session to reveal that his mother had recently passed away. Caught by surprise, I attempted to sympathize, because he was obviously in pain, but I'd like to emphasize this was our second date. What follows is my best recollection of our conversation.
Me: Oh, I'm sorry to hear that. Was she --
Him: She actually passed away on this couch.
Me: You mean this couch we're sitting on?
Him: Yeah. I just wanted you to know because, well, I still feel her here. Her spirit is here in the house.
Me: Like, right now? Oh, OK. I don't know if I'm really ready to meet your mom. Could you maybe turn on the lights?
Him: Well, it doesn't bother me that she's here. So, if it doesn't bother you...
Me: [Silently screaming]
I tried to bounce back, but my lady parts shut the door that night, AOL Messenger-style. Still, I always wonder what might have happened if potentially boning him in front of his mother's ghost did not, in fact, bother me.
As a girl growing up, you dream of a few big moments. Prom. Your sweet sixteen. Your first date and possibly first kiss with a real, live, non-relative boy. For me, all of those aligned into one, perfect evening. Or they would have, anyway, if life hadn't been a total dick.
His name was Jeff and he was impossibly sweet. A tall football-playing Junior to my gangly Sophomore, Jeff was the kind of guy you lingered around certain lockers just to look at.
I'm still not sure why he chose me. We were on our way back from a church ski trip, sunburned enough to resemble badgers with rosacea, and somehow, magically, seated together. We fell asleep with our heads clunked. (Well, he did. I was faking it.) When he woke up, with skin peeling adorably off every portion of his face, he asked me to prom.
He didn't know when he extended the invitation that prom would fall on my 16th birthday. He also didn't know that I had no experience with guys and would build this up to be THE BIGGEST THING THAT HAD EVER HAPPENED TO ME AND EVER WOULD AGAIN, FOREVER. He couldn't have. He was a 17 year-old dude.
Fortunately by this point, I'd seen enough John Hughes films to know that prom, sixteenth birthdays and first kisses were all magical and nothing would go wrong in the end. That's why I didn't worry when I stopped hearing as much from Jeff closer to our big day. Occasionally, I'd get a short chat in the hall. A polite but difficult to read note in my locker. With nothing to gauge any of this against, I was fairly sure that it was all quite normal. I mean he was voted Best Eyes for Christ's sake. Best Eyes don't lie.
Even when I heard a rumor that he'd been spotted in Cozumel with a Senior -- a Cheerleading Senior -- I brushed it all off. And when my twisted parents made me get braces a week before prom, I said, "Fuck it, you can't bring down my party. It's all going to work out." I liked him that much.
Jeff was an hour and a half late to pick me up, which is awkward when you're sitting with your family, on your birthday, in a dress that looks like a Beverly Hills 90210 princess threw up all over it. When he did arrive, I watched my father's expression shift from nervous, to angry, to baffled. Jeff was wearing an all-white suit, or it would have been if he hadn't climbed underneath his car to remove a pestering tree branch on his way over. Really, he was wearing a mostly white suit with a lot of automobile grease and forest crap stuck to it
The problem with being barely 16 at prom is that most everyone else is just a little older. Well, that's only a problem if your date spends the evening at another table, chatting up a cheerleader and returning to occasionally give you a thumbs up.
See, that's what John Hughes doesn't tell you. Hughes encourages the belief that guys want the quirky girl who sews her own clothes and listens to punk. But that's all crap. They want her: The seductive, busty cheerleader who goes to tanning beds after practice and owns 13 bikinis.
Of course they do. By the end of prom, I probably wanted her. He almost pushed me out of the car immediately after prom, then peeled out to rendezvous with that babe, I couldn't blame him. Instead, I called my best friend, who was also fresh off an awkward prom. We walked to the spot halfway between our houses and got more stoned than either of us had ever been bold enough to get before. And that's the really important lesson, the one Hughes forgets to mention in his many, many movies. In life, most dates suck, but getting stoned with your best friend in really fancy clothes afterward will always be awesome.
Senior prom was really fun for the first hour and a half or so. In my Al's Formal Wear rental tux, I was impressing my girlfriend with skills and a run of luck at the blackjack table that made me feel like some stoner James Bond. It was going to get even better, though, as my hoodlum friends had managed to procure a keg and psychedelic mushrooms and rented a houseboat on Lake Lewisville.
I'd mowed a lot of lawns to help pay our share. There were four or five couples along with a couple of terminally dateless friends set to lift anchor at midnight, and that's when the party would really start. We'd need to leave at 11 to make sure we had time to change into our own clothes and get there on time -- it was understood that the boat wouldn't wait for anyone.
As the hour grew nearer, my girlfriend started getting antsy and morose. I couldn't figure out what was wrong, and in trying to suss out why she seemed so sad, I asked a question so monumentally boneheaded, sexist and insensitive that to this day, more than 15 years later, I still cringe thinking about it and can't bring myself to repeat it.
About 10:45, I asked -- rhetorically, I assumed -- if she was ready to cash in our chips and get going.
"No, I'm having fun here," she said. "Can't we stay longer?"
Sure, a little while more, I agreed. The gaming is kind of fun, I guess. Maybe we could leave about 11:30, drive straight to the dock and change on the boat -- where, you know, there will be drugs, booze and no adults?
I got more and more nervous as the minutes ticked closer and closer to too late, finally throwing chips away on stupid wagers hoping that running out would be incentive to leave. But she managed to hold on to hers with smart, conservative betting, and was unmoved by reasoning, pleading and passive-aggressive dickishness. Eleven-thirty passed, but instead of rolling with the new plan of having fun with the hundreds of other classmates who also wouldn't be on the boat that night, I sulked and felt sorry for myself, steaming over the $100 or however much it was I'd pitched in.
We had a makeout session in my car in her apartment parking lot when I dropped her off, but it felt half-assed and went no further than usual, since we weren't enjoying the privacy afforded by the thin walls of a cheap houseboat cabin. My parents were still up when I got home, surprised to see me so early, so I had to relieve an aching case of blueballs quietly in my bedroom closet, hoping the extra layer of drywall would muffle the noise and my frustrated, self-loathing weeping as I mentally replayed all the stupid things I'd said.
As it turns out, I wasn't the only one in a closet that night. She came out as a lesbian just a few months later.
I was a junior in high school, then a senior. He was slightly older and worked at the cool pet store, not the shitty depressing one. He had black hair and a tattoo of a tarantula on his shoulder. I considered all of these things to be super dreamy, and batted my eyes at him incessantly whenever I went in to buy mealworms for my hedgehog. Other than awkwardly hitting on me in front my mom one time, though, he never made a move.
That first summer after college, I came home and I ran into Tarantula Guy at a punk show someone was throwing in a storage unit. He offered me a PBR and asked if I wanted to take a walk. We went a little ways and sat on a curb under a streetlamp. I pretended to drink my beer.
"I never asked you your last name," I said, for some reason.
"I don't have one," he replied. He looked away and scratched at his tarantula tattoo for a while. Then he told me a story about being a tow-truck driver. We talked about the pet store burning down. That was a bummer, we agreed. Long silence.
"How old are you?" I asked, in a flailing attempt to re-start the conversation.
"I'm not," he said. More silence.
He also didn't want to talk about what he did for work now, or where he lived, or where he was from. He also didn't ask me any questions, like, say, my name, which I realized at some point he absolutely did not know. After an abortive attempt to make out with the side of my face, he wandered off and we never saw each other again. I heard he's a bouncer now, or possibly that he's in jail. I don't think either of those things are true.
I am no good at dating. Is anyone good at dating? It's excruciating. The whole damn thing. So much judgment. So many fried mozzarella sticks.
My first-ever first date was to the seventh grade square-dancing festival at Stonewall Jackson Elementary in 1967. My date was not the boy I had a crush on. I don't remember who my date was, except he was the runner-up and he had sweaty hands. We square-danced to "Little Liza Jane" and then walked over to the Kip's Big Boy that used to be on Mockingbird and Greenville where the 24-Hour Fitness is now. I ordered a hot fudge sundae and the waitress spilled it on my white square-dance skirt, the one with silver rickrack around the hem. She brought me another one for free. In retrospect, this was one of my best first dates. At least it ended with free ice cream.
Worst first dates by decade:
1970s: A New Year's Eve prom in the ballroom of the old Statler Hilton. My date was a cute boy from the swim team. He forgot to bring any money (ha!) so I had to buy the tickets with all the cash I had on me: $22. At midnight he kissed me and it felt like he was mopping my face with his lips. He tasted like the Everclear he'd smuggled in and kept swigging like a gangster in a speakeasy. His dad picked us up in a Cadillac with fins.
1980s: The age of personal ads. I went out on one personal ad date. He had weird eyes and wore a radio station T-shirt to our happy hour rendezvous at a Lower Greenville fern bar. If you were born after 1990 you have never been to a fern bar. He looked at the wine list and ordered "a giraffe of white wine." I giggled, thinking he was kidding. He was not.
1990s: Blind date set up by a friend. He was 90 minutes late and his first words upon seeing me were, "You aren't as fat as I thought you'd be."
2000s: My mail carrier in Toledo, Ohio, flirted with me. I asked him out for dinner. He was recently divorced and lived with his mother. Over pizza, I told a few amusing stories about interviewing celebrities. When I got to one about a famous TV talk show host who had hit on me during a phone interview, my date said, "If he'd seen you, he wouldn't have done that." I'm paraphrasing because I've tried not to remember it as "Why would he hit on a hag like you?" For the rest of the time I lived in Toledo, I dreaded getting mail.
2010s: Now in my 50s, it's no longer dating; it's carbon dating. I'm not unhappy as a spinster, but as comedian Rita Rudner once observed, "I like a man in life, just not in my house." I still enjoy infotaining when I can find a guy my age who isn't a Republican or doing community service as an alternative to jail. Good grammar is a must. Breathing unassisted is a bonus. Three out of four limbs, very good. (I gave up square-dancing ages ago.) Now I try to do first dates at breakfast. It's cheap and fast then I'm free the rest of the day to do whatever I please. After my 40-year high school reunion, however, I had a late lunch with the one and only single guy left from my graduating class. He's very smart and successful, and, like me, never married. "I see you've maintained your height," he said as we hugged hello. We both laughed. He was kidding. Garçon, a giraffe of your finest chablis, if you please!
I'm having drinks with a guy -- we'll call him K -- at the Libertine. Things are going well. We're swapping stories about relocating to Texas, having overly elaborate drinks that occasionally involve glasses on fire. You know, usual first-date things.
Suddenly a man next to me, wearing a parka and looking to be his 40s, asks if I'm gay. He's alone and has been standing next to us for a while.
"Yep," I say. I figure one syllable is enough before I feel out where this is heading.
He looks at K. "And you?"
"Now look," the guy says, "I'm not a fag, or whatever it is that's OK to call you guys now, but I fucking love you guys. You know, girls, they play games and they're coy, but a gay guy is gonna tell you exactly what they're thinking. And you're just more fucking fun."
It goes on like this for a while, for the last half hour of our night. He keeps complimenting K., telling him that he's clearly slumming by hanging out with me. There are veiled references to a traveling girlfriend and blunt ones about how tacky the girls in the bar are.
"What kind of woman goes out with her hair up in a clip?" he asks. "And eats French fries and drinks beer?" By now he's pointing conspicuously at people. "That's just not refined, you know. To me a woman should always be drinking white wine or something classy."
Eventually I give up trying to discreetly signal the bartender to close my tab and just flag ham down. I pay, we get up and put our coats on, and our new friend, whose name we never got, shakes our hands.
"I'm not gay," he says again, in case we forgot, "but I fucking love you homos."