Tough Questions: What’s the Worst Date You’ve Ever Been On?


Every week we ask everyone who hangs out around here to answer a tough question. This week:

What’s the worst date you’ve ever been on?

Rules are simple: so, like, what do you do for fun? Dating is extremely stressful, because it requires exactly the right blend of being honest about yourself and shielding a near-stranger from the horrible truth of who you are. Dating is exciting because it’s full of possibility, but one of those possibilities is that it will go really, really badly. What’s your worst experience?

Alex Russell

There have been a few, but nothing will ever dethrone the very first one. I was 13 and painfully shy, but I met a girl at a friend’s party and we hit it off. I don’t know how much one can “hit it off” at 13, but it at least went well enough that she wanted to see me again. She invited me to her friend’s party the next week and told me it was a “fancy dress-up party.” I showed up in loafers and a suit coat, and everyone else was ready for what was clearly a swimming event. I never figured out if she made an honest mistake or if she was just evil. As some kind of gesture to show I was a good sport, I jumped in and swam in my 13-year-old “nice clothes” anyway. An auspicious start.

Jonathan May

I’ve been on a ton of horrible dates. But one time really takes the cake. I was seeing this guy who wasn’t really my type, but he was really into me, so I thought, “What the heck? Okay.” He wanted to take me to a movie, which is my least favorite kind of date because you don’t actually talk to the other person at all. Well, I wanted to see Tree of Life, which (trust me) is not a date film. Halfway through the film, as Jessica Chastain’s character hovers mid-air, I started to cry because I was struck by the movie’s poetic beauty. It was at this exact moment that he tried to hold my hand. I can’t describe how little I wanted anyone to touch me right then and there in the dark theater, with a billion emotions roiling within me. That was the camel’s straw. Afterward, I begged off going for dinner due to a headache, which I didn’t even have to fabricate at that point. Ugh, the worst.

Brent Hopkins

The worst date I went on was with a Korean lady who started off by informing me that she always wanted to go out with a black dude but that I wasn’t that black in skin color and actions. I guess she saw me as training wheels to the “real” thing or something. I tried to explain that his was not something that was okay to say, which led me down this road of trying to figure out what type of backhanded offensive things I could say to her to get her to understand. So, yeah, I had a date that was entirely based on racism and stereotyping and it was, the suck, as they say.

Andrew Findlay

I met my wife when I was 18, so the only bad dates I’ve ever been on were bad teenager dates, where neither of you know what to do or what you want, and both of you are just super awkward for basically all the time you spend together. It was ten years ago though man, so I don’t know.

Gardner Mounce

The weirdest date I’ve ever been on happened when I was in 8th grade and was dating a girl I’ll call C. C and I were at her house one night watching a movie. C decided it’d be fun to get in her hot tub out back. We did. After a little while, her mom, who we both thought was upstairs sleeping, came out with a camera and asked if she could take a picture of us kissing. Ladies and gentlemen, I have never felt more uncomfortable. I wish I could say I declined, but I didn’t. I rest uneasy knowing that her mom probably still looks at that thing.

Colton Royle

I once went on a date with a woman who advocated for a fascist educational system. “Maybe some people with lower IQ’s should be taught what to think.” We report. You decide.


  1. A girl I was dating in Korea wanted me to meet her brother so we went on a double date. For some reason she decided, presumably minutes before the date, that she wanted to torpedo the relationship and decided to go off about how 9/11 was an inside job all night. We were all sitting on rope swings in a tiki-themed bar full of sand and Christmas lights. The whole memory is so trippy I’m still not always convinced I didn’t dream it up.

  2. I wouldn’t consider this a worst date…more like a fine date with a weird ending. I went out with this guy on a nice date downtown. We had pizza and walked around by the river. Nothing too special. But at the end of the date, when I was about to go inside, this sly guy turned a hug into a butt grab. And acted like it was the most normal thing. By far the creepiest hug I’ve ever received.

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