Chelsea Handler recently vented about her ‘bad’ date with ‘cheap’ Bobby Flay, but she’s not the only one who’s had a tough time while looking for love.
The 51-year-old comedian lambasted the A-list TV chef after he sent her and her pals a room service order but left her with the bill.
Yet, her experience is far from unique, proving that wealth and fame offer no immunity against subpar dating experiences.
Superstars like Britney Spears, Billie Eilish, Charlize Theron, Selena Gomez and even heartthrob Justin Bieber have previously detailed their dating horror stories.
Singer Kelly Clarkson even confessed to running out in the middle of a date and leaving her clueless companion behind.
From one man asking an A-list actress to ‘make out with his nose’ to a pop superstar spilling spaghetti all over his date, the Daily Mail takes a look at the worst celebrity courtships.
Chelsea Handler recently vented about her ‘bad’ date with ‘cheap’ Bobby Flay (R), but she’s not the only one who’s had a tough time while looking for love
Britney Spears
Pop princess Spears has surprisingly suffered through more than one bad date.
The Toxic hitmaker detailed a ‘really bad date’ she went on in a 2016 interview with Marie Claire UK.
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Chelsea Handler slams ‘cheap’ celebrity chef who took her on ‘bad’ ‘messy’ date
‘I had a really bad date. I mean, it was really bad,’ she recalled.
‘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.’
‘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 explained.
Spears noted that being famous doesn’t shield celebrities from experiencing rejection.
‘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.’
Sadly, that wasn’t her only bad romantic encounter.
Pop princess Britney Spears previously recalled a date with a man who ‘looked like a lizard’ which prompted her to ‘immediately’ leave; Spears seen in 2018
She also previously recalled a date with a man who ‘looked like a lizard’ in an interview with Jonathan Ross.
‘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 said.
‘I went with this one guy, and he looked like a lizard. Like, I was so scared… I was like, “Holy s**t, he looks just like a lizard,” and I had to go. [I left] immediately.’
Billie Eilish
Before she was a Grammy-winning singer, Eilish endured the sting of a terrible first date.
Not only did her date leave her at the movie theater, he also complained about her kissing skills.
Billie Eilish previously shared that during her teenage years a date left her at the movie theater after complaining about her kissing skills; She is seen in 2020
‘He kissed me and then he said, “That was not as magical as I thought it would be,”” Eilish recalled on the Howard Stern show.
The mishap occurred when Eilish was just 13, meaning the Ocean Eyes hitmaker has had plenty of time to refine her dating game since then.
‘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.’
However, it worked out in Eilish’s favor, as she admitted: ‘Dude is hella ugly now.’
Charlize Theron
Theron previously recounted how a ‘lovely’ dinner with a ‘super handsome man’ suddenly turned awkward after he made a bizarre request.
The South African-born beauty recalled how the two were kissing in the car after driving back to her home following dinner, during an appearance on Jimmy Kimmel Live.
Charlize Theron recounted how a ‘lovely’ dinner with a ‘super handsome man’ suddenly turned awkward after he asked her to ‘Make out with my nose’; Theron seen in April
‘He pulled away and he whispered, “Make out with my nose,”‘ she said.
Despite the strange request the Mad Max: Fury Road star tried to please her companion.
‘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.”‘
Melissa McCarthy
Like Handler, comedian Melissa McCarthy had also encountered a stingy date, who later surprised her with an explicit request.
McCarthy discussed the cheap suitor while appearing on Jimmy Kimmel Live, revealing that throughout their dinner the man complained about the restaurant’s prices.
He told her that he could prepare the food himself for much cheaper at home.
After dinner, he proceeded to stump her with a NSFW request.
Like Handler, comedian Melissa McCarthy had also encountered a stingy date, who later surprised her with an explicit request; Seen in February
‘As we approach my building he’s like, “So… I got this thing in my bag,”‘ she recalled him saying.
‘I got it from this guy at work. 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,’ she explained.
‘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!’
Kelly Clarkson
Clarkson’s date was so bad that she fled halfway through.
The singer recalled the experience on The Ellen DeGeneres Show, telling the host that the man was insecure about his height.
‘He was 5′ 2″, and I’m 5’ 3.”‘
Kelly Clarkson previously spoke about going on a date was so bad that she fled halfway through
‘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,’ she explained.
‘And I withstood an hour. And then I went to the bathroom and I left… I couldn’t take it.’
Jennifer Aniston and Jon Stewart
Brad Pitt’s ex-wife Jennifer Aniston ended up being a bad date for late night host Jon Stewart.
When she stopped by the The Daily Show in 2010, Stewart recalled how he asked her out for a date in New York City, but she ended up bringing all her friends.
‘I asked you out. 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.”‘
Jennifer Aniston (L) ended up being a bad date for late night host Jon Stewart (R) after she brought all her friends along
However, that wasn’t Aniston’s recollection.
‘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.
Nicole Kidman and Jimmy Fallon
Jimmy Fallon famously fumbled his chance to date actress Nicole Kidman.
In 2015 she revealed that she was set up on a date with Fallon by a friend, but that he didn’t realize it was a date.
‘And you wouldn’t talk,’ she told him while appearing on his show.
Jimmy Fallon famously fumbled his chance to date actress Nicole Kidman after he ‘wouldn’t talk’ on their date, prompting her to question whether he was gay
‘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.”‘
She even questioned if Fallon was attracted to women, and revealed that she thought to herself, ‘Maybe he’s gay.’
Justin Bieber
Though he’s now happily married to model Hailey Bieber, the Baby singer has also endured his share of bad dates.
He previously recalled how a clumsy move on his part ended with his female companion wearing her dinner.
Justin Bieber once recalled how a clumsy move on his part ended with his female companion being covered in spaghetti; Bieber seen in February
‘I took a girl out for a first date to an Italian restaurant and spilled spaghetti all over her,’ a 16-year-old Bieber told Girl’s Life.
‘It was terrible and embarrassing. She never went out with me again,’ he said.
Selena Gomez
Bieber’s ex-girlfriend Selena Gomez previously called out another famous singer for ditching her during their date.
Gomez once called into former beau Nick Jonas’ Radio 1 interview to mock him for trying to keep their fling ‘private’ by walking away from her during a date in the park.
‘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,’ Jonas said.
Selena Gomez previously called out Nick Jonas for ditching her during their date; The two seen in 2015
‘I was like, “It’d be better if we stood about 25 feet apart.”‘
However, it all worked out for the best, as Gomez went on to meet her now husband Benny Blanco, while Jonas went on to marry Indian actress Priyanka Chopra.
Jameela Jamil
British actress and activist British actress Jameela Jamil revealed how a ‘booty call’ ended up with her date losing his front teeth.
‘How do I tell this again legally?’ she joked during an appearance on the Today show, before diving into the story of her worst date ever.
British actress and activist British actress Jameela Jamil revealed how a ‘booty call’ ended up with her date losing his front teeth; She is seen in January
‘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,’ Jamil recalled.
‘He broke all of his front teeth,’ the star 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.’
Emma Watson
Harry Potter star Emma Watson was left flabbergasted when a potential suitor turned out to be fat-phobic.
Harry Potter star Emma Watson was left flabbergasted when a potential suitor turned out to be fat-phobic; She is pictured in 2025
The actress recalled her unpleasant experience in a 2013 interview with The Telegraph.
‘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 quipped.
Mindy Kaling
The Office star Mindy Kaling recalled how once she got her hopes up for a date, only to find out that it wasn’t one.
He also turned out to be cheap and made her pay for half of the bill.
The Office star Mindy Kaling once went on a date where the man talked to her about another woman he wanted to go out with; She is seen May 28
‘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,’ she shared on Reddit.
‘He was just a straight dude who was psyched to have dinner with me in a platonic way.’
Worst of all, her companion then proceeded to tell her who he would like to go out with.
‘He talked about an actress he really wanted to date and we split the check.’
