Celebrity3 min(s) read
Published 10:09 27 May 2026 GMT
Comedian Chelsea Handler has revealed some of her worst dating experiences with male celebrities.
During an appearance on Kristin Cavallari’s Let’s Be Honest podcast, Handler, 51, was asked to share a “bad celebrity date story” that she has never spoken about publicly.
She claimed that after “someone hooked” her up with celebrity chef Bobby Flay, the pair began “talking on the phone [and] flirting a little bit.”
Flay then insisted on ordering room service to the hotel she was staying in “with some girlfriends”, but the gesture was not as sweet as it sounds.
Recalling their first awkward interaction, the former Chelsea Lately host explained: “He knew the hotel well. He wanted to order … food for us. He was like, ‘Let me order your food for you. I love that hotel.'”
Shockingly, the man who owns multiple restaurants, businesses, and hosted his own TV show ordered the food, then, according to Handler, left her with the bill.
Reminiscing about the stingy move, Handler said: “And I’m like, ‘What?'”.
When she confided in someone about the failed flirting attempt, they reportedly responded with: “‘Oh yeah. He’s really cheap.’ And I was like, ‘Oh, I hate cheap.'”
Handler then added: “If you’re penurious, I’m not interested in you. I’m generous, and I like people to be generous with their money.”
In spite of the sour taste in her mouth following the food faux pas, Handler went on a proper date with Flay, but, unsurprisingly, “it was not a match”.
Although she did not go into too much detail, she said: “It was just, like, messy.”
However, Flay was not the only male celebrity that the star spoke out about on the podcast. She also shared that she once went on a date with an A-list actor, who “was so boring”, but sadly, she did not name him.
Recalling how the date came about, she said: "We were flirting, and then I made the move.
"So I made the move, and he was receptive, and we were hanging out, and I saw him, and we went on a date, and it was unbearable. And I worked hard."
Explaining why the pair didn’t work out romantically, she said a big problem for her was that "he was so serious about himself as an actor," and spent a lot of time "talking about acting in a way I can’t take seriously."
Handler even claimed: "He didn't ask me one question about myself."
When asked about what she is looking for in a romantic partner on the Not Skinny But Not Fat podcast in January, she said: “If I'm gonna date a guy, they're gonna have to party.
"I wanna party. I like to get loose. And by the way, I'm 50 years old.”
