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People Share Their Worst First Dates Ever

"On the third date he asked me if I would be interested in a threesome... with his sister."
Photo by Milles Studio via Stocksy

The road to love is paved with hundreds of horrible first dates. Everyone has been to dinner with a guy or girl who smells or makes offensive comments. Bad dates are as common as the flu, so we asked people about their worst experiences. Here are a few of the worst and weirdest.

The Boy Who Was Drugged with Ritalin as a Child

I used to have a party trick with guys on dates where I would ask, "What's the craziest thing you believe?" Guys would say they thought Mase and Diddy were a couple, the moon landing was fake, or the Mafia killed JFK, and we'd have a laugh. But once on a date, I lightheartedly asked a guy the question, and he got very serious and intense. Finally he said, "When I was eight, I believed that my house was filled with demons. I would see them crawling on the walls and flying towards me like dark shadows, but it turned out my parents were secretly drugging me with Ritalin, and it was causing me to hallucinate." I still went home with him. – Zelda*

Read more: Can Cheating Improve Your Relationship?

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The Boy Who Didn't Know I Had a Boyfriend

I'd had a boyfriend for years when an acquaintance sent an email to me and one of her male friends saying she thought we'd really hit it off. I thought she assumed we'd get along as friends, so I agreed, but moments before leaving the house, I reread the email and realized it was a blind date. Not knowing what to do, I showed up to our meal and immediately mentioned my boyfriend. We then sat through a very, very awkward first date before parting ways and never speaking again.

-Myra*

The Girl Who Lied About Her Age

I met a cute girl at a fundraiser, and we agreed to get dinner and go to a concert. When I showed up at the restaurant a week later, she had totally shaved her head, offering zero explanation. I didn't want to judge or ask her, "What happened to all of your hair?" so I sat patiently through the meal thinking she would acknowledge the drastic change. Instead, she told me that she was seeing a fortune teller and that I should try and "connect with a higher power" too. After dinner finished, we went to the concert venue, where she was turned away at the door for having a fake ID. At that point she admitted to me that she was actually 19 years old, almost a decade younger than me, and I told her I didn't think it was going to work out between us.

-Jamal

The Director Who Wanted to Get Me Pregnant

A very handsome and successful director asked me out. Everything was going well until he asked me, "So if we had sex and I got you pregnant tonight, do you think that we'd keep the baby?" I was totally flabbergasted, so he continued, "I think, 60/40, we'd have the kid. I mean, I'm in that place in my life now where I think, with the right woman, why not?" I kept seeing him because I'm an idiot and one day he gave me one of his scripts to punch up; he was apparently so enamored by his own banter that he had included our conversation in one of the scenes in the movie. It's in post-production now, so our bad date will be coming to a theater near you soon.

-Nina

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The Boy Who Also Fucked His Sister

When I was 20, I was asked out by a regular at the coffee shop where I worked. At the date, he talked about his sister a little too much, but not enough to totally creep me out. He just made a lot of sweeping and ill-timed statements about her virtues. It wasn't a total turnoff, and we hooked up a few times, but on the third date he asked me if I would be interested in a threesome… with his sister. After I refused, he asked me to not tell anyone that they were in love, not because he thought it was weird, but because, "My sister and I are really private people."

- Kara*

The Girl Who Spent the Date Sexting a Famous Man

A girl I chatted with briefly on Tinder texted me out of the blue to meet up. She came over to my apartment and sat on my lap, but she spent the entire night texting. I had to ask: "Who the hell are you texting? I'm getting very mixed signals here." She turned her phone towards me, and her screen blew up with sext after sext from the name of a very famous former politician. I thought she had just changed the contact name, but she swore that it was really him, and showed me her months of Twitter DMs with his check-marked account. It was undeniable that it was really him. We sat together for a moment watching the messages flood into her phone. It ended when he invited her to meet up and she left to go see him.

-Nick*

The Boy with the Vision Boards

I hit it off with a guy on our first date. We went back to his place, and his bedroom was full of homemade vision boards filled with sports cars and women with giant breasts in bikinis. He seemed really embarrassed that he forgot to take them down, but I had to admit the boards might have worked because I was a girl with big boobs standing in his bedroom.

-Laura*

* Name has been changed