Celebrity Celebrities' Worst Dates Being rich and famous doesn't exempt you from dating nightmares! These stars shared the romantic encounters that left them reeling By Lydia Price Updated on March 22, 2023 01:40 PM Share Tweet Pin Email Trending Videos 01 of 18 Jameela Jamil Jon Kopaloff/WireImage "How do I tell this again legally?" Jamil jokingly said as she recalled what happened during her worst date ever on Today. "I had a man take several steps in my apartment on what was supposed to be my first ever booty call. He collapsed three steps in." "He broke all of his front teeth," she added. "They flew across my apartment. He split his chin open and collapsed, and it was because he had misused a drug that excites a man's sausage." 02 of 18 Charlize Theron JEAN-BAPTISTE LACROIX/AFP/Getty The actress 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.'" 03 of 18 Tiffany Haddish MICHAEL TRAN/AFP via Getty Images "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. 04 of 18 Selena Gomez Selena Gomez. Tibrina Hobson/Getty 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.'" 05 of 18 Kelly Clarkson Kelly Clarkson. Weiss Eubanks/NBCUniversal/NBCU Photo Bank via Getty "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." 06 of 18 Mindy Kaling Kevin Mazur/Getty "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." 07 of 18 Justin Bieber Justin Bieber. Jon Kopaloff/Getty Images A 16-year-old Bieber had a major dating disaster. "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. No word on whether he's ever ruined wife Hailey Bieber's outfit. 08 of 18 Camila Cabello Presley Ann/FilmMagic "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." 09 of 18 Emma Watson Jemal Countess/Getty Images In 2013, Watson told The Telegraph about finding herself out with an ultra-vain suitor. "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 said. 10 of 18 Dylan Sprouse Dylan Sprouse. Dia Dipasupil/WireImage Even a big star like Sprouse gets nervous for first dates. "I'm a very sweaty guy," he told Elle. "One time I decided to wear a light green shirt to a date, and [had armpit sweat] basically down — because I was so nervous — all the way down to my waist." He added of his confession, "Everyone I've ever been on a date with would be like, 'That was my date.'" 11 of 18 Awkwafina Natalie Thomson/imageSPACE/Shutterstock "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 Farewell 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. 12 of 18 Jenny Slate Mark Davis/Getty "I got set up on a blind date," Slate shared on the podcast Talk Easy with Sam Fragoso. "He comes around the corner inside the restaurant, and this dude 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. ...' His chainmail is like getting caught on stuff ... I'm mortified, and also just mad. He's trying my pasta with the chainmail clinking across and stuff, it's insane." 13 of 18 Billie Eilish Billie Eilish. "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." 14 of 18 Melissa McCarthy Gilbert Flores/Variety via Getty 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!" 15 of 18 Aisha Tyler Jason LaVeris/FilmMagic 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. 16 of 18 Troye Sivan Troye Sivan. In a February 2018 interview with PopCrush, the "Take Yourself Home" singer recalled meeting up with a guy he met on a dating app, only to see him fire up Grindr and start checking out other options. "It was a while ago, back in a time when it was a little bit less accepted and a little bit more scary," he said. "I was like, 'Okay. I think I'm just gonna go home.'" 17 of 18 Dove Cameron TOUT ONLY DO NOT USE Dove Cameron Talks New Music, Staying Busy in Quarantine and More!. Getty Images 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." 18 of 18 Lilly Singh Lilly Singh. Neilson Barnard/Getty "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.