11 Celeb Dating Fails That Will Make You Feel Somewhat Better About Your Love Life

Even the most glamorous celebrities go on bad dates, harbor unrequited crushes, get dumped and vomit uncontrollably on their one-year anniversaries

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Even the most glamorous celebrities go on bad dates, harbor unrequited crushes, get dumped and vomit uncontrollably on their one-year anniversaries.

Whether these celebrities were hopelessly in love or looking for love, things didn’t work out quite as planned.

We now present you with 11 not-so-rom-com-worthy dating anecdotes from celebrities – all followed by my own real-life experiences that are almost the same, but ultimately upsetting in a different kind of way.

1. That time Amy Schumer got food poisoning while celebrating her one-year anniversary with her boyfriend.

The story: During an appearance on The Ellen DeGeneres Show, Amy Schumer opened up about her not-so-romantic trip to Paris with her boyfriend Ben Hanisch, in which the two each had a “violent” battle with food poisoning.


Schumer says she and her boyfriend took turns in a thin-walled hotel bathroom when the food poisoning hit, with Hanisch throwing up and Schumer being stricken with “machine gun” release of … well, no. 2.

“I knew it was over,” Schumer joked. “I’m yelling at him, like, ‘It was so great dating you! I wish you the best luck! You’re gonna meet the greatest girl!’ But I knew, I knew it was over.” (Spoiler alert: It wasn’t over. They are still very much in love.)

It happened to me: I was taking antibiotics for a tooth infection that made me so nauseous that I vomited in the Uber on my way to the apartment of a hookup who didn’t even like me that much.

2. That time Harry Styles randomly showed up at Lindsay Lohan’s hotel room at 2 a.m. and she was confused.

The story: The Mean Girls actress told The Sun that she turned down Styles one night when he came to her hotel room at 2 a.m. and knocked on her door. “I didn’t know it was him,” she said. “He was in a suit. I said, ‘Well, you’re very good-looking – can I help you?’ That was it.” Burnnnnnnnnnnn.

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It happened to me: A random guy once entered my apartment at 3 a.m. because he thought it was his apartment.

3. That time Jon Stewart asked Jennifer Aniston out … and she brought all her friends.

The story: When Aniston visited The Daily Show in 2010, Stewart reminded her that they’d shared a romantic Italian meal in N.Y.C. more than a decade ago. But their recollections of the evening were … somewhat conflicting.

“I asked you out,” Stewart said. “And it was lovely. I remember you brought so many of your friends. And I remember thinking, ‘She’s so excited to be on a date with me, she wants me to get to know her posse.'”

Aniston remembered things differently. “If I remember correctly, wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?'” she asked.

Josiah Kamau/BuzzFoto/Getty

It happened to me: A guy I was hooking up with brought a different girl to my birthday party. There was cake, so it ended up fine!

4. That time Liam Neeson proposed to Brooke Shields and then dumped her.

The story: In her 2014 memoir, There Was a Little Girl, Shields reveals she’d been wooed by Liam Neeson. She dated the actor in 1992 and admits that she was impressed by his movie-star status. He “wooed me with his brogue, his poetry and his s—-y choice of cheap pinot grigio wine,” she writes. Things got serious after just three months and he asked her to marry him, sans ring. That year, they spent a tipsy Christmas together in New York, and later that night, Neeson told Brooke he had to fly to Los Angeles to check on his house. She asked him to call her when he arrived, but he said it would be “late, darlin’.” He never called.

Johns PKI/Splash News Online

It happened to me: A guy ghosted me after inviting me to his holiday office party. I almost went to the party, too, just to spite him, but ended up eating a large pepperoni pizza in bed, using my stomach as a plate.

5. That time Justin Bieber moved in too quickly with the woman he was dating.

The story: Years after his most high-profile relationship, Bieber is doing some reflecting on his past relationships … and why they had to end. “I learned a lot,” he said of his on-again, off-again romance with Selena Gomez, which lasted three years. “I moved in with my girlfriend when I was 18. Started my own life with her. It was a marriage kind of thing. Living with a girl, it was just too much at that age,” he told Complex. “But we were so in love. Nothing else mattered.”


It happened to me: Impulsive and drunk, my boyfriend and I got a Costco card together. We broke up weeks later.

6. That time (by which we mean, those times) Britney Spears went on a slew of uncomfortable dates with a guy who just wasn’t that into her.

The story: In August, the Glory singer opened up to Marie Claire UK about about her awful dating experiences. “I had a really bad date. I mean, it was really bad,” Spears, 34, said. “I’ve been single for ages and had a date with a guy I liked. I was getting anxious, worrying he wouldn’t like me. In the evening, I got on the scales, and I had lost 6 lbs.”

Kevin Mazur/Getty Images for Music Choice

“We went to the movies, but I could tell right away it wasn’t working. It was sort of awkward. So after the movie, I came home, and that was it,” she said, adding, “He just wasn’t that into me. I liked him. He knew that. But he definitely didn’t feel the same. It happens to everybody. Being famous doesn’t make you any different.”

It happened to me: In the middle of a first date, a guy went to go to the bathroom and never came back.

7. That time Nicole Kidman went on a date with Jimmy Fallon, but he didn’t know it was a date.

The story: In 2015, the actress revealed that a friend had set her and Fallon up … but that the Tonight Show host hadn’t realized it was a date. “And you wouldn’t talk,” she told him, years later on his show. “You wouldn’t say anything, and then you put a video game on or something … and so after about an hour and a half, I thought, ‘He has no interest, this is so embarrassing’ … and then I was like, ‘Maybe he’s gay.'”

JIMMY FALLON AND <a href="https://people.com/tag/nicole-kidman/" data-inlink="true">NICOLE KIDMAN</a>
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It happened to me: A meet-up I assumed to be a date turned out to be “networking coffee.” I still don’t know what networking is.

8. That time Britney Spears went on a date with someone who looked like a lizard.

The story: We had to also include this Spears story, as the pop star is full of hilarious dating anecdotes (and is our single spirit animal). She recently talked about a time she gave an automatic hard pass on an unfortunate blind date.

“I have a friend at home, and he randomly sets me up with people every now and then on dates. It’s just awkward because there’s so many times that you meet people and it’s just too awkward, and you just don’t feel right,” she told Jonathan Ross. “I went with this one guy, and he looked like a lizard. Like, I was so scared … I was like, ‘Holy s—, he looks just like a lizard,’ and I had to go. [I left] immediately.”

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We’ve all been there.

It happened to me: I’ve been on at least three different dates with guys who look identical to lizards.

9. That time Vanessa Bayer went to a college formal, flirted with a guy, he left and she woke up covered in vomit.

The story: The Trainwreck star and SNL castmate opened up about a less-than-romantic encounter she had with her crush while attending the University of Pennsylvania. “There was a formal I went to in college where I matched this huge guy drink for drink, and then I ended up throwing up on myself, but not really knowing about it and being like, ‘We should hang out more,'” Bayer said. “And he was like, ‘I’m gonna go home.’ And then I woke up a few hours later and realized that I had thrown up all over my dress. [I was like], ‘Oh, that wasn’t the coolest look.'”

Cindy Ord/Getty

It happened to me: Literally this exact same thing, word-for-word.

10. That time Kelly Osbourne broke her wrist on her first date … ever.

The story: “He went to kiss me and I got scared, because I was still very much a prude,” the TV personality told PEOPLE of her very first date. “I leaned back and fell down three stairs onto the street, broke my wrist and ran away from him.”

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It happened to me: While I’ve never sprained or broken bones on a date, I have had acid indigestion on every date I’ve ever been on. So, like, on three occasions.

11. That time Taylor Swift was dumped during a 27-second phone call.

The story: In 2008, Swift addressed those rumors that her ex Joe Jonas had broken up with her over a short phone call. “It’s all right – I’m cool,” the singer said on The Ellen DeGeneres Show. “You know what, it’s like, when I find that person that is right for me, he’ll be wonderful. When I look at that person, I’m not even going to remember the boy who broke up with me over the phone in 27 seconds when I was 18.”

<a href="https://people.com/tag/taylor-swift/" data-inlink="true">Taylor Swift</a> - News
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It happened to me: When I was 18, a guy told me he didn’t want to keep seeing me by telling a friend to Facebook message me. I’ll never bounce back from this.

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