12 stars who opened up about their bad dates with other celebrities
12 stars who opened up about their bad dates with other celebrities
Britt HayesTue, August 25, 2026 at 4:34 PM UTC
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Nicole Kidman; Gina Rodriguez; Drew BarrymoreCredit: Cindy Ord/WireImage; Emma McIntyre/WireImage; Cindy Ord/Getty
Everyone has bad dating stories, including celebrities. But few of them are willing to spill the tea on the bad dates they’ve been on with other celebrities.
Think about it: No one wants to broadcast that they went on a bad date with a current or potential coworker, particularly in an industry where those stories can become the subject of articles like this one. As readers, we love to hear the hot goss about stars (they really are just like us! Kind of!), so when one of them is willing to share intel on another celeb, it’s especially thrilling.
These stories are rare enough that a single anecdote can linger in the pop culture consciousness for years — another reason why most celebs aren’t going to make a habit of putting each other on blast. A perfect example: Chelsea Handler opened upmonths ago about the time she went on a bad date with celebrity chef Bobby Flay, and we’re still talking about it.
Handler is just one of the names on this list of celebrities who have opened up about the awkward, cringe-inducing, and just-plain-bad dates they’ve had with other famous people.
01 of 12
Sara Foster on George Clooney
George Clooney in 2025; Sara Foster in 2026Credit: Joe Maher/Getty; Stefanie Keenan/Getty
George Clooney was once known as Hollywood’s most eligible bachelor, but at least one person in Hollywood was immune to his charms: actress and producer Sara Foster.
“Do you guys know that I got set up with George Clooney like 30 years ago and it was such a blah?” Foster revealed to her sister and cohost Erin Foster on a January 2026 episode of their podcast, The World’s First Podcast. When prompted to explain, the Nobody Wants This producer said, “Rande [Gerber] and Cindy [Crawford] tried to set me up with him, like, when I was 24 maybe? And the four of us met and it was just such a hard no.”
“I remember just thinking, ‘Oh, he is so old,’” Foster added. “I always say that when I see these young girls dating older guys. Like, yes, of course, sometimes it makes sense, and it’s all the things. [But] I’ve never understood a 19-year-old that’s into a 40-year-old. I just always thought that was so weird.”
02 of 12
Kristin Cavallari on a “very famous man”
Kristin Cavallari in 2026Credit: Star Max/GC Images
Kristin Cavallari is extremely polite for refusing to name the celebrity who turned their second date into a nightmare version of “show and tell.” In a June 2026 episode of her Let’s Be Honest podcast, Cavallari recalled an incident from about four years earlier, when she went on “two really great dates” with an unnamed celebrity. “Honestly, like two of the best dates of my life,” she said.
On their second date, the celeb booked a suite at the Beverly Hills Hotel, where they spent the day swimming. After showering (separately), they were dining on the patio when her date had a radical idea. “He’s like, ‘You know how when you first start dating someone you have those insecurities about your body and like you just want to like get them over with?’” she recalled. “And I’m like, ‘Sure there’s little things,’ and he’s like, ‘Can I just tell you mine?’”
According to Cavallari, her date confessed, “I have a mole on my d---.” She asked how bad it was, and he said that it wasn’t “that bad,” but was definitely “noticeable.” That’s when the unnamed celeb asked if he could show Cavallari the alleged mole. “So, he pulls out his d‑‑‑,” she said. “I’m literally sitting there going, I don’t see anything. I think he said it was like more of like a flesh-colored, like a white-like mole. Like I’m not even kidding.”
In hindsight, Cavallari realized that this was probably the celeb’s way of exposing himself to women. “And then later, I was thinking about it and I was like, ‘Oh my god, that’s what he tells every f‑‑‑ing girl to get his d‑‑‑ out,’” she said.
03 of 12
Nicole Kidman and Jimmy Fallon
Nicole Kidman in 2026; Jimmy Fallon in 2023Credit: Cindy Ord/WireImage; Rosalind O'Connor/Getty
Nicole Kidman stopped by The Tonight Show to promote Paddington in 2015, only to reveal that she and host Jimmy Fallon had an awkward run-in several years prior. “I don’t remember if you remember this, but we’ve met before,” Fallon said, to which Kidman replied, “Oh, I remember.”
Fallon went on to recall his version of their awkward earlier meeting, which occurred sometime before the 2005 release of Kidman’s Bewitched. A friend said he was bringing Kidman over to Fallon’s apartment and gave him the impression that it had something to do with the movie. “I just remember I liked you,” said Kidman, who apparently thought she was going on a date with the Saturday Night Live star.
“So I go over there, and you’re there in a baseball cap and nothing, and you wouldn’t talk. You didn’t say anything,” Kidman recalled. “And then you put a video game on or something, and I’m like, ‘This is so bad.’ And you didn’t talk at all. So after about an hour and a half I thought, ‘He has no interest, this is so embarrassing.’ And I left and went, ‘OK, no chemistry,’ and I went, ‘Maybe he’s gay.’”
It’s truly inconceivable that anyone could fumble Nicole Kidman this hard.
04 of 12
Matthew Perry on Cameron Diaz
Matthew Perry in 2017; Cameron Diaz in 2026Credit: Steve Granitz/WireImage; Kristina Bumphrey/Getty
Matthew Perry’s memoir is filled with candid details about the Friends star’s life, from his struggles with addiction to his dating history. In Friends, Lovers, and the Big Terrible Thing, the late actor recounted being set up with Cameron Diaz shortly after her split from Justin Timberlake in 2007. “The date was at a dinner party with a bunch of other people, but upon seeing me, Cameron got almost instantly stoned — it was clear that she wasn’t interested in me at all,” Perry wrote.
“But the party went on nevertheless, and at one point we were all playing a game — Pictionary, I think,” the actor continued. “As she was drawing, I said something witty to Cameron, to which she said, ‘Oh, come on!’ and proceeded to punch me in the shoulder. Or, at least, that’s what she meant to do, but she missed and, instead, punched me smack in the side of my face.”
Perry wasn’t exactly unfazed, either. “‘Are you f---ing kidding me?’ I said, realizing I’d just been punched in the face by Cameron Diaz.”
05 of 12
Katie Couric and Larry King
Katie Couric in 2025; Larry King in 2017Credit: Taylor Hill/Getty; Dia Dipasupil/Getty
If you go on a date with a journalist, you should probably avoid any behavior that might be considered newsworthy. Thankfully for us, two journalists were involved in this particular story. During an appearance on Jimmy Kimmel Live! in 2013, Katie Couric recalled an awkward date she went on with fellow newscaster Larry King a few decades prior.
“I was about 30 years old and I was in this period of my life where I [thought], ‘I’m going to go out with anybody who asks me because you learn something any time you go out with a new person,’” Couric recalled. King picked her up in a Lincoln Town Car and drove her to an Italian restaurant. Having recently undergone bypass surgery, he ordered veal poached in chicken stock.
“We had a nice enough time,” Couric said, “and we’re going home, and I see that we’re going over [Arlington] Memorial Bridge — and this is not the way to my apartment. I said, ‘Larry, where are we going?’ And he said, ‘My place.’ Oh mother of god.” When they arrived, Couric noted that King’s walls were “covered with proclamations [to] Larry King Day, keys to every city in the country.”
“So we sat there, and what can I say?” Couric continued. “He lunged … and I started laughing a little bit because the whole situation was out of a bad Lifetime movie. I said, ‘Larry, you are such a nice man, but I would like to meet someone a little closer to my age.’”
Shortly after the Kimmel appearance, King appeared on Couric’s talk show, Katie, to share his slightly different recollection of the evening. In King’s telling, the two shared a kiss before he drove Couric home because he had to do a radio show. When they arrived at Couric’s apartment, he said, she told him he couldn’t come inside because she had a roommate — despite Couric having already revealed on Kimmel that she didn’t actually have one.
06 of 12
Chelsea Handler on Bobby Flay
Chelsea Handler in 2026; Bobby Flay in 2026Credit: Taylor Hill/FilmMagic; John Nacion/Getty
Comedian Chelsea Handler took the title of Kristin Cavallari’s podcast — Let’s Be Honest — seriously during her May 2026 appearance, when she shared the story of a bad experience with a certain celebrity chef.
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“I went on a date with Bobby Flay, that was pretty bad,” said Handler, who revealed that she was connected with the celeb chef by a mutual friend. “We were talking on the phone [and] flirting a little bit,” she continued. “I was at a hotel with some girlfriends… He knew the hotel well and he’s like — he wanted to order room service, food for us. He was like, ‘Let me order your food for you. I love that hotel.’”
Handler said she accepted Flay’s offer, only to be surprised when the order showed up and she was handed the check. “I’m like, ‘What?’” she recalled. “And then somebody was like, ‘Oh, yeah. He’s really cheap.’ And I was like, ‘Oh, I hate cheap.’”
The comedian said she ended up going on a date with Flay anyway, but “it was not a match.”
07 of 12
Drew Barrymore and Christian Bale
Drew Barrymore in 2026; Christian Bale in 2026Credit: Cindy Ord/Getty; David Jon/Getty
While reflecting on his early acting career in a 2012 interview, Christian Bale told GQ Australia about his one and only date with fellow child star Drew Barrymore. “We went to see some bloody awful horror film, and that was the end of it. She never called again,” said Bale, who was 13 when he went on the ill-fated date.
Three years later, Barrymore finally told her side of the story on an episode of Watch What Happens Live. When host Andy Cohen asked why she didn’t call Bale after the date, Barrymore said, “I don’t know. He was so nice.”
“I had a lot of fish to fry,” the actress continued. “I had big problems in my world, for like, many years,” she said, referring to her highly publicized struggles as a young actress. “Boys were secondary.”
08 of 12
Jennifer Aniston and Jon Stewart
Jennifer Aniston in 2026; Jon Stewart in 2025Credit: Steve Granitz/FilmMagic; Phillip Faraone/Getty
Jennifer Aniston’s highly publicized relationship history includes an intriguing footnote: she almost dated Jon Stewart. Well, sort of. In 2010, the former Friends star stopped by The Daily Show, where Stewart asked if she recalled having dinner with him at an Italian restaurant years earlier. In Stewart’s recollection, it was supposed to be a date, but Aniston remembered things a little differently.
“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.’”
“If I remember correctly,” Aniston said, “wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?’”
Whatever happened (or didn’t) between the two, Stewart was still fond of Aniston, telling the star, “You were lovely then and lovely now.”
09 of 12
Patricia Arquette on Mark Rogowski
Patricia Arquette at the Austin Film Society’s AFS Cinema on July 18, 2026Credit: Rick Kern/Getty
In 2021, Patricia Arquette responded to a Twitter prompt asking for people to share their most awkward dating stories. “Second date. Pro skateboarder. Really cute. Friends with my friends,” Arquette wrote in a since-deleted post, according to PEOPLE. “We made out, but something about how he kissed me freaked me out. I gave him a fake number. Years later he killed his girlfriend.”
Naturally, the internet sleuths got to work and it wasn’t long before Arquette confirmed the identity of the man in question: Mark “Gator” Rogowski, a professional skateboarder who sexually assaulted and murdered model Jessica Bergsten in March 1991. It should be noted that Bergsten wasn’t Rogowski’s girlfriend, but she was a friend of his ex-girlfriend, Brandi McClain.
When Arquette was asked what was so troubling about kissing Rogowski, she replied, “It felt aggressive. Like pushing me back hard with his jaw and it felt like it was angry.” She concluded, “Moral to the story — Trust your instincts.”
10 of 12
Gina Rodriguez on an unnamed “socialite”
Gina Rodriguez attends a ‘Matlock’ FYC event on June 3, 2026, in Los AngelesCredit: Emma McIntyre/WireImage
Most of the stories on this list are of the cringe-inducing variety, so here’s an inspirational version, courtesy of Gina Rodriguez. Before she was cast on Jane the Virgin, the actress went on a “terrible” date with an unnamed “socialite.”
“I had a terrible date with this super-socialite guy when I first moved to L.A.,” Rodriguez told Glamour in 2015. “He was so pompous. I took out my money, put it on the table, and said, ‘I’m not having a good time, so I’m going to pay for this and leave.’ I walked out thinking, Look at you, badass!”
While Rodriguez didn’t get into specifics, it’s a great reminder that, when possible, you can and should walk away from a bad date before it gets worse.
11 of 12
Heather Locklear on Tom Cruise
Tom Cruise in 2026; Heather Locklear in 2021Credit: David Jon/Getty; Kimberly White/Getty
During an appearance at 90s Con Florida in 2024, Heather Locklear treated attendees to a very special bad-date story. According to PEOPLE, the Melrose Place vet said she met Tom Cruise when they were both young actors auditioning for the same project.
“So at that time he was just like this little baby boy [and] I feel like I was a little bit older, and he ended up coming over to my house with Sean Penn,” Locklear recalled. “And they were just nice, but he was very, ‘yes ma’am’ to me, and I was like, ‘okay, sir.’” The actress, who described herself as more of a “rock and roll girl” back then, said that Cruise “didn’t quite cut it.”
“We went out dancing to Club Lingerie at that time and, and I’ve said this before, I mean, he was really cute,” explained Locklear, who said that Cruise pulled a move that would later flaunt in Risky Business, sliding across the floor on his knees. “He actually did that before [the movie], and I was dancing along like, ‘Do you stop dancing if they’re down there?” she wondered.
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12 of 12
Shia LaBeouf on Hilary Duff
Shia LaBeouf in 2025; Hilary Duff in 2026Credit: Dave Benett/WireImage; David Becker/Getty
Let us return now to 2011, before the name Shia LaBeouf had darker connotations. While promoting that year’s Transformers: Dark of the Moon, LaBeouf opened up to Details magazine — perhaps a little too much — about his personal life, which included a brief, eyebrow-raising mention of a fellow former Disney Channel star: Hilary Duff.
The profile referenced an “ill-fated sushi dinner” between LaBeouf and Duff, which the actor described as “probably the worst date either of us has ever had.”
Duff does not appear to have publicly responded to LaBeouf’s account of their date.
on Entertainment Weekly
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