Chelsea Handler Reveals 'Bad' Date with Bobby Flay, Calls Him 'Cheap': 'It Was Not a Match'

Julia MooreTue, May 26, 2026 at 5:08 PM UTC

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Chelsea Handler, Bobby Flay
Credit: Lets Be Honest/YouTube; Cindy Ord/Getty -

Chelsea Handler once went on a bad date with Bobby Flay, she revealed on Kristin Cavallari's podcast, Let's Be Honest

The comedian said she and the chef were "not a match"

Of her dating philosophy, Handler said, "I want to have a good, sexy affair. I don't want to be a couple"

Chelsea Handler revealed why she and Bobby Flay are not a romantic match.

On the Tuesday, May 26 episode of Kristin Cavallari's podcast, Let's Be Honest, the comedian was asked if she had any "bad" celebrity date stories, and she responded by revealing that she'd been flirting with Flay for a time, but things didn't exactly go well between them.

"I went on a date with Bobby Flay that was pretty bad," Handler, 51, said. "Bad everything."

She had been connected to Flay, 61, by a friend, and said they were "talking on the phone, flirting a little bit," when he offered to order her room service during a hotel stay.

"I was at a hotel with some girlfriends, and I think we were filming for Netflix," she said. "I don't remember where we were. ... He knew the hotel well, and ... he wanted to order me room service. He's like, 'Let me order your food for you, I love that hotel.'"

"He orders me food — he's going to love this. This is somebody I don't mind incriminating," she quipped. When the food arrived, the hotel "brought me the bill," Handler said.

Chelsea Handler on 'Let's Be Honest'
Credit: Lets Be Honest/YouTube

"I'm like, what? And then somebody was like, 'Oh, yeah, he's really cheap. He's really cheap.' And I was like, oh, I hate cheap. If you're penurious, I'm not interested in you. I'm generous, and I like people to be generous with their money."

Despite the room service snafu, Handler and Flay did "end up going on a date, and it was just not a match," she said. "It was messy."

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PEOPLE reached out to a rep for Flay for comment.

Handler also spilled that she'd had another less-than-ideal date with a celebrity, whose identity she kept private. She said the date they went on was "unbearable."

She said she "made the move" on him after they started talking, but on their date, "He was so serious about himself as an actor, and he was talking about acting in a way that I cannot take seriously."

"He couldn't stop talking about himself, and he didn't ask me one question about myself," she said. "I felt like I was 25 years old and had to, like, make up a lie to get away, because I had really pursued him. But then once I sat down with him, I was like, no, no. I was like, you're so boring, and you're so annoying."

She added, "I was like, are you going to get drunk or something? Like, let's loosen this f---ing convo up."

Chelsea Handler at 'The Roast of Kevin Hart' Red Carpet at Netflix Is A Joke Fest on May 10, 2026
Credit: Christopher Polk/Variety via Getty

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When it comes to dating, Handler, who confirmed on the podcast that she split from her latest boyfriend, said she's "not a long-term person."

"I'm not interested in anything that comes after the six-month relationship mark. I'm not interested in dealing with your family or your issues. I am not interested," she said. "I don't want to be part of a unit. I want to have a good, sexy affair. I don't want to be a couple."

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Source: “AOL Entertainment”