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My Scummy Valentine

The only thing worse than Valentine’s Day is a crappy Valentine’s Day. A handful of TMN writers and editors dish (anonymously) on their worst dates—crying men, rugby brawls, and a dislocated sacroiliac joint.

Walter Martin and Paloma Muñoz, Traveler CCXVIII, 2007. Courtesy of the artists.

Writer 1: I was dating this guy who was very cute. At least I hope he was very cute, because otherwise I have no excuse.

Once, when we were arguing about the Iraq war, and whether Bush or Cheney had been the force behind it, he said, “Who the fuck is Dick Cheney?” He wasn’t being funny. He really didn’t know the (then) vice-president of the United States. I sat there, half-horrified and half-amazed. I felt like an anthropologist who had stumbled on a new species. What would he say next? What other alarming deficits of knowledge did this attractive man contain?

He did other crude things, like tugging down the top of my shirt to get a peek at my cleavage, and flirting with the female bartender. I don’t know if I was lonely, or trolling for material—no, I’m sorry, I do know, and the answer is both—but this was not our last date, and I’m not proud of that.


Writer 2: I arrived at his front door and he was crying. Bawling. Red in the face, like he had been crying for days. Apparently his ex-girlfriend had stolen his credit card number and maxed it out. I had met him only once before and didn’t know what to do or say, so I said what I always say when I’m at a loss and the obvious options like, “Do you want to be alone?” elude me. I said, “Do you want to go for a walk?”

Which we did. For three very long hours. He cried as we walked down the street, as we looked over the water while crossing a bridge, as we waited for the Walk sign, and as I ran into a coffee shop for a coffee. When we arrived back at his house he—still crying—cooked eggs. His cigarette ash fell into the pan.


Editor 1: On our first date she told me, at length, about how she had an ovarian cyst removed and how the doctors kept it because it had hair and teeth. There was no second date. Although we eventually did get married.


I went out with a Jane Austen-loving Irish construction worker to see my ex-boyfriend’s band play.

Writer 3: My worst date was my first date. I was a freshman at an all-boys high school. My friend Will, who was six months older and about six years wiser, insisted that I triple-date with him and another friend to the freshman prom. He even knew a girl I could take—which was 100 percent more girls than I knew. I said yes.

At the prom, we split up, as boys and girls do at freshman proms. Finally, as couples tentatively stepped onto the floor, I sought out my date.

I asked her for a dance. She looked me over, as if for the first time. I could tell she was building up to something, a prepared line. Finally, she said with a muffled laugh, “With you?” Someone chuckled. I fled.

Later, she found me in the coatroom. I had been there a while. She was looking for her parka. When she noticed me sitting beside the coat pile, she asked, “Why the long face?” and went back to her friends.


Editor 2: Valuable dating lesson I have learned: Never go to a second location with a dude who calls you five minutes before your scheduled date to see if you are here already, because he is and he doesn’t see you yet. The next thing you know, you’re both two $12 cocktails in, he’s yelling at you about how Bloomberg is actually a good mayor who has had to face incredible adversity and what would you do if you were trying to work with such a terrible city council, and upon your return from the bathroom (where you were devising a clever escape plan), you discover he has left you. With the tab.


Writer 4: Blind date, sushi restaurant, Manhattan pre-internet dating. A coworker set me up with a college friend of hers. We met outside the restaurant. About 10 minutes into conversation, she said she hoped to be married and pregnant soon, just like her older sister. She asked me, did I want kids soon, too? We were both 22.

The conversation went downhill from there, completely one-sided. I was trying to figure out a way to leave when a glass wall shattered down my neck. Another customer had been leaving, weaving drunkenly, and walked straight into the glass wall positioned directly behind me. The noise was huge. Instant pandemonium, people gasping, my date screaming. There was glass in my hair, down my shirt. The hostess whisked our fish away, said our meal was on the house, and asked us to leave.

Outside, the girl wanted to know if I wanted to get coffee, but I begged off, saying I needed to go home and shower off the glass. Best excuse ever.


Writer 5: In high school, I went on a date with a girl who made AIDS jokes in the car on the way to watch Derek Jarman’s Blue.


Editor 3: I was about 20. I’d just met this girl. A small group of friends wanted to check out the new Aronofsky movie Requiem for a Dream. I wanted to see it because, hey, Pi was so fun and smart and experimental, right? I vaguely understood it was about heroin users. The girl went with us, the poor thing. After the movie she said, “So now I want to go home and cry,” which is an appropriate response to that movie. We didn’t go out again.


Never go to a second location with a dude who calls you five minutes before your scheduled date to see if you are here already, because he is and he doesn’t see you yet.

Editor 4: On a blind date at a hip, Lower East Side establishment with a man wearing colorful clothes that accompanied his colorful name, all I heard was white noise. To be fair, he did do some nodding.

After a pause so long it would have sounded like the apocalypse had it happened on the radio, I asked, “So did anything interesting happen today?” Grasping for content. Just grasping.

“No,” he said.

“Nothing at all?”

“No,” he said again. He wasn’t nasty or curt; he just seemed to believe that his life was very, very bland. That, or he was shy bordering on comatose. I like to think that he has since met the right girl and it’s opened up a whole spectrum of life—and conversation—to him.


Writer 6: I once went out with a Jane Austen-loving Irish construction worker to see my ex-boyfriend’s band play, because sometimes I make bad choices.

The bar was packed, so I brushed it off when someone bumped into me and spilled about a teaspoon of my beer. My date was both less forgiving and a former boxer. I tried to stop the fight but the other guy was a rugby player and his whole team wanted in on the fun. The rugby player chivalrously pushed me out of harm’s way, at least—straight into the stage, where I took out my ex’s mic stand and amp before hitting the floor.

A stampeding crowd, I learned, flows through a room like a tidal wave. Five minutes later my date had a black eye, I had a partially dislocated sacroiliac joint, and the rugby team had been arrested. My ass still aches every time it rains.


Editor 5: I accidentally went on a date in New York while on holiday a few years ago. “Accidentally” because I didn’t realize it was a date until I ordered a large, whole, undressed crab and realized, “Oh, this isn’t very elegant, is it?” And then, “Oh, shit, this is a date, isn’t it?”

After dinner we went to a gig of some noise/drone act that made conversation difficult and we ended up awkwardly grinding in her bed. My face and fingers were coated with crab flesh for days.


Editor 6: I once went on a date with someone who wrote for Thought Catalog.


Writer 7: She phoned up one Saturday afternoon and asked if I'd like to come round that evening and maybe stay over. There would be a family meal and board games. Sure, I said.

My mum drove me there (it was too far to cycle) and, as promised, her family and I sat down for a meal and board games. Her little sister was sent up to bed. We watched a bit of TV. Her parents yawned and went to bed themselves. We were left by ourselves. Suddenly, she was all over me, snogging as if her life depended on it. It was only then that the penny dropped. "Ahh!" I thought. "This is a date. Right."

We snogged and groped feverishly until her dad came back downstairs and smirked at us.

TMN’s Contributing Writers know where to find the purple couch. Long live the pan flute, mini mafia, and Michael Jackson. More by The Writers