This story is over 5 years old.

Question Of The Day

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

Laughing at strangers' pathetic pangs of existential loneliness.

One way to find people to fuck/love is to “date,” which means you go someplace with someone you don’t know all that well and see if you want to fuck/love each other. Sometimes this turns out well, sometimes it turns out HILARIOUS. We went out to ask folks about their romantic misadventures so we could laugh at their pathetic pangs of existential loneliness.

Matt: It was probably the worst fuck of my life also. I went to a bar, had a few drinks with her. It was actually set up through a friend of mine, and he promised me this girl wanted to go off and the whole nine. Got her back to the apartment and it was literally like, “Holy shit have you ever seen a cock before in your life?” It was that bad. She sounded like a hunchback… [makes weird sex noise]


Did she not know what to do or was she just terrified?
All of the above, just… fuck. It was weird, dude, the most bizarre thing in world. Finally when she was done I called my friend freaking out, like, “Yo what the fuck?” and he was like, “Dude, I’m so sorry.”

Are you still friends with him?
Yeah, I’m still friends with him. The friendship transcended the experience, but it was fucking brutal.

Shaggy: There are many, many of them. When I was in high school I had a valentine but I had no money to buy her a gift. I ended up finding a beat-up Barney toy and giving it to her. She bought me a dozen roses. So she was really bummed by my gift.

But that was your fault.

What about dates where the person you were dating did something shitty?
[Laughs] Every girl is terrible! Let me think for a second… Since it’s the 21st century, here’s a 21st-century one. I dated a girl and we were dating for six months. She bought a ticket to California. Instead of telling me about it, she tweeted it to her Twitter followers who she's never met in her fuckin’ life before she told me. How about that?

Matul: I really don’t know because I had an arranged marriage.

Yeah, I’m Indian. I've never actually dated.

How did that happen?
I went to India. I met a decent number of people and when I met my wife I wanted to marry her. About two months later we got married.

When was that?
Three years ago.

The two of you are happy?
Absolutely. She’s coming to meet me right now and we’re going to lunch.


David: The worst first date I ever went on… At dinner, she told me she had contracted herpes and gave me a laundry list of things that she wasn’t going to do that night. On the very first date.

How did you meet this girl?
Through a friend. It was a relative of his wife.

And you’re still on good terms with him?
Oh yeah, we’ve been friends since we were 14.

But maybe you don’t trust his judgment of women now?
I wouldn’t trust him again if that tells you anything. But no, he has not tried to set me up with anyone since then.

Melissa: It wasn’t the first date, it was the third or fourth date, but this guy was trying to kiss my neck and when he pulled away this big line of snot was hanging from my neck to his nose. And it just really killed the mood.

Did you go out with him again? 
I tried to explain to him later that it wasn’t gonna work out. I think the visual image of that just ruined it for me. I mean, he’s terribly intelligent—a little socially awkward—but can you erase that image from your memory?

Jennifer: I got trick dated once.

What is “trick dated”?
It’s like where they set you up thinking that “Oh we’re just gonna go hang out” but then it turns into a date and they have expectations. Super awkward. So it’s like, “Yeah let’s go to lunch. Let’s get a sandwich or whatever,” so we got a sandwich and he’s like, “I’ll pay for it” and I’m like, “OK. You don’t have to do that.”

Warning sign.
So then we went to a museum, an art museum, and he’s like, “I’ll get it, don’t worry.” I’m like, “OK.” And then he takes me back to my apartment and I’m like, “I’m gonna GO now.” And he’s like, “Can I see you again?” and I’m like, “Yeah, I mean, I’ll see you tomorrow in class.” So yeah, it was a trick date. It was the worst.

It was just some guy from school who had a thing for you?
Yeah. Super awkward.

Previously – What's the Worst Vacation You've Ever Been On?