From Billie Eilish to Ariana Grande, and Bella Thorne to Justin Bieber, here are 27 celebrities who’ve also had terrible dating experiences.
1. Billie Eilish
Via Instagram
“He kissed me and then he said, ‘That was not as magical as I thought it would be,’” Eilish told Howard Stern about a movie date she went on when she was 13. “He was super rich, and his butler — literally his butler — [took him home]. He left and I was stuck there, no one told me they were going to leave … Dude is hella ugly now.”
2. Charlize Theron
Via Instagram
Charlize Theron enjoyed a “lovely” dinner with a “super handsome” man, but he made an unusual request when they started kissing in the car after driving to her home. “He pulled away and he whispered, ‘Make out with my nose,’” she said on Jimmy Kimmel Live.
“I didn’t want to, like, mess it up, so I gave him a little peck on the nose, and he was like, ‘No, make out with it.’”
3. Emma Watson
Via Instagram
“The worst date I’ve ever been on was a guy who told me he couldn’t be friends with fat people or anyone who was unattractive. I realized pretty quickly that he was a nutter,” she told The Telegraph in 2013.
4. Michael Kors
“In my twenties, I went to meet my date at a really chic, fashionable restaurant,” Michael Kors said in Sarah Wexler’s book “Awful First Dates.” “I wasn’t dressed up necessarily, but I had one a nice shirt and jeans. My date showed up in cutoffs and a tank top,” he said. “I knew half the people in the restaurant, who were all looking at me like ‘Who is this guy with Michael Kors?’ It was so embarrassing. My tip: Always have your first date at a casual place.”
5. Tiffany Haddish
Via Instagram
“I went on a date with a guy to wash his clothes. He said we were going to dinner, and we got dinner, and then we went to the laundry house and washed [his] clothes,” the comedian told TMZ. When the reporter said that the laundromat outing didn’t sound “that bad,” Haddish begged to differ. “That’s horrible. I’m not no damn maid,” she said.
6. Camila Cabello
Via Instagram
“He refused to tell me the name of the movie we’re going to see. We get there, and it’s Ouija Board,” the singer explained. “I think he thought that it was going to be super cute, and that he’d be making the moves on me because I was scared. But [in this theater] you could lay down, and there were blankets. I literally just had the blanket over my head the whole time.”
7. Kelly Osbourne
Via Instagram
“He went to kiss me and I got scared, because I was still very much a prude,” Kelly told PEOPLE about her very first date ever.“ I leaned back and fell down three stairs onto the street, broke my wrist and ran away from him.”
8. Selena Gomez
Via Instagram
Gomez called into former flame Nick Jonas’ Radio 1 interview to tease him about that time he ditched her in an attempt to keep their relationship “private.” “She was unhappy that her Central Park experience was ruined by the fact that I walked about 20 feet away from her, even though they were taking pictures of us and obviously we were there together,” he confessed. “I was like, ‘It’d be better if we stood about 25 feet apart.’”
9. Kelly Clarkson
Via Instagram
“He was 5′ 2″, and I’m 5′ 3″ … Obviously, I went out with you, so it didn’t bother me. But he proceeded to talk about his height for like a solid hour,” Clarkson said on The Ellen DeGeneres Show. “And I withstood an hour. And then I … I went to the bathroom and I left … I couldn’t take it.”
10. Mindy Kaling
Via Instagram
“The worst date I’ve ever been on was with a guy who I was super excited about, really attracted to, and then on the date it became apparent that it WASN’T a date,” Kaling shared on Reddit. “He was just a straight dude who was psyched to have dinner with me in a platonic way. He talked about an actress he really wanted to date and we split the check.”
11. Justin Bieber
Via Instagram
“I took a girl out for a first date to an Italian restaurant and spilled spaghetti all over her. It was terrible and embarrassing. She never went out with me again,” he told Girl’s Life at the time.
12. Awkwafina
Via Instagram
“The waitress comes and I’m about to order, and he was like, ‘We’ll take the steak.’ One steak, for both of us,” The Raya And The Last Dragon star said of a blind date in a Vogue “Sad Hot Girls” video. “And then he says, ‘I want it well done.’ I was like, ‘How dare you? Who eats a well-done steak?!’ That’s like eating a bed. The steak comes, and he proceeds to cut up the steak into baby pieces, like one would do for a small bird.” In addition to his controlling dining habits, the man had a “hyper intellectualism” that rubbed Awkwafina the wrong way. Although she actually ended up seeing him for a couple more dates, she finally called it quits after noticing she wasn’t herself around him. “I just realized that I’m enough. And if you can’t get with that, then, ‘bye,’” the actress said.
13. Jenny Slate
Via Instagram
“I got set up on a blind date by the husband of my best girlfriend, and he set me up with a man that he didn’t know very well and she had never met,” Jenny Slate said on “Talk Easy with Sam Fragoso.” “He comes around the corner inside the restaurant… this dude, and I’m not kidding, is dressed in full chainmail. He’s got a full authentic knight’s costume on, including a floor-length tabard, which I called a tunic and then he corrected me and was like, ‘It’s actually a tabard.’”
14. Ariana Grande
Via Instagram
“A few years ago I was on a date and when we were kissing I suddenly got the worst ever nosebleed. We went back to his car to sort it out and at the same time my friends walked past and saw me bleeding – they thought I was being killed! Luckily, though, nothing that bad’s happened recently,” Ari confessed to CelebsNow.
15. Lucy Hale
Via Instagram
“I was on a date with a guy once, and he wasn’t aware that I could see his cell phone,” the Pretty Little Liars actress told Glamour. “And the fact that he was actually texting romantic messages to another girl.”
16. Melissa McCarthy
Via Instagram
On Jimmy Kimmel Live, McCarthy recalled an outing with a cheap suitor that quickly went from bad to creepy AF. To begin with, the man spent dinner complaining about the restaurant’s not-unreasonable prices, and mansplaining that he could prepare food for much cheaper at home. After delivering a hilarious impression of the man’s meal behavior, McCarthy revealed the NSFW way the date ended. “As we approach my building he’s like, ‘So … I got this thing in my bag,’” she recounted him saying. “‘I got it from this guy at work. It’s like a — um — it’s this thing, it’s in my bag. Well, it’s a ring.’ And I was like, ‘What?’ I’ll just say, it’s not a ring for your finger or your toes. I had never — it’s my one and only offering of that. [And] after the date going terribly… And he got it from his friend at work, it’s not even new!”
17. Aisha Tyler
Via Instagram
Tyler and a college love interest made the poor decision to see Mississippi Burning, an “intense” film about the civil rights movement, on their first date. “I burst into tears after, like, the first three minutes and sobbed uncontrollably through the entire movie,” she said on Watch What Happens Live. “And we didn’t really know each other like that, so he was just [awkwardly] like, ‘there, there,’ the whole movie. And it was at college and we just, like, avoided each other for four years,” the Archer star added.
18. Dove Cameron
Via Instagram
Cameron told PopBuzz about a suitor who ended up having serious envy issues. “We went out to get crepes and on the receipt the waitress had written ‘your girl is like sunshine,” she said, adding that her date immediately got huffy after reading the note. “He was like, ‘I just don’t know why nobody thinks I’m the sunshine!’ … It was the craziest, and just devolved from there.”
19. Britney Spears
“I have a friend at home and he randomly sets me up with people every now and then on dates,” Britney Spears said on “The Jonathan Ross Show.” “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… 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.”
20. Lilly Singh
Via Instagram
“Once I went on date and this dude just yelled at the waiter because he forgot his dipping sauce. I’m just like, ‘My uterus fell out,’” Singh said in a video for Vogue. “I’ve [gone] on dates where the guy doesn’t even ask me any questions. He’ll just talk on, and on, and on about his gym routine,” she added
21. Bella Thorne
Via Instagram
Back in the day, Thorne got her first period while out on a date. “I was wearing an all-white dress. So my mom was like, ‘Let’s not say anything, I’m just going to take you to Target,’” she told Hollywood Life. “I end up getting really upset because he does notice and he’s like, ‘Oh, it’s fine, who cares!,’ and I was like ‘I CARE!’ and I started bawling in Target.”
22. Eliza Doolittle
“I went on a blind date, and after that I never, ever did it again. The guy repeated everything he said twice. He’d say, ‘So, how are you? How are you?’ and I’d say I was fine, and he’d say, ‘Good, good.’ Or ‘I’ll have the mac and cheese please, please. Yeah, the mac and cheese’ I don’t know if there was something actually wrong with him or if it was just a bad habit, but no more blind dates after that.”
23. Bear Grylls
“I made a picnic up on a mountain for a girl, with tables and chairs and three courses,” he told The Huffington Post. “It took me a full day to carry it all up there. But then she never showed, and the wind and rain blew it. The whole night was a washout.”
24. Khloe Kardashian
Via Instagram
“I met this guy in New York and we stayed connected as friends and then one time, I was on iChat, and IM with him, and a naked girl walks in the background and all of a sudden the computer just shuts, like stops,” she recalled to E! Online.”And then he texted me an hour later, like, ‘Sorry that was my sister,’ and I was like, ‘uhhh.’”
25. Christina Milian
Via Instagram
“I dated a guy who had really bad breath. Really bad. The elevator, the car, everything smelled like his breath. Even gum didn’t help!”
26. Ellie Kemper
Via Instagram
“The worst [date I’ve been on] was a setup, a blind date,” Ellie Kemper told Glamour. “When your friends pick someone out for you, they say, ‘Oh, you’ll like this guy.’ Then you meet him, and you’re going, ‘You thought I would like him?!’ This particular guy was rude and was much older than I was. He seemed pained to be there. I was like, ‘Why would this person even want to go on a date?’”
27. Paul Adelstein
“I had a blind date during which the woman asked me — an hour into it — if she could cut me if we ended up [being intimate]. I was trying to be calm, so I asked, ‘With what?’ She said, ‘A knife.’ And I said, ‘Where?’ And she said, ‘Chest.’ I said, ‘Yeah… no.’ It was just crazy.”
