Chelsea Handler Shares ‘Bad Celebrity Date' Story About ‘Cheap' Bobby Flay

Chelsea Handler is sharing two new dating horror stories, both involving high-profile men in Hollywood.

During an appearance on Kristin Cavallari's Let's Be Honest podcast on Tuesday, May 26, the comedian was asked whether she's had "a bad celebrity date story that we don't know about," and Handler didn't hold back.

Not only did she spill on a particularly "unbearable" date with an actor, she also name-dropped celebrity chef Bobby Flay in the process.

‘Bad' Date with Bobby Flay

Not hesitating to name Flay, Handler claimed that the pair went out on a date "that was pretty bad."

First, she explained that one of their mutual friends connected them, so they began talking on the phone and "flirting a little bit."

Then, according to Handler, she was staying at a hotel with some girlfriends when Flay said he "knew the hotel well, and he wanted to order me room service."

"He's like, ‘Let me order food for you, I love that hotel,'" she said, sarcastically adding that Flay was "going to love" that she was sharing this story. "This is somebody I don't mind incriminating," she added.

Though Flay had allegedly ordered the food for her and her friends, Handler said he didn't take care of the bill.

"But then they brought me the bill and I'm like, ‘What?' And then somebody was like, ‘Oh yeah, he's really cheap,'" said Handler. "And I was like, 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."

She still, however, went out on a real date with him-though quickly learned "it's not a match" between them. "It was just like, it was messy," said Handler.

"I love you for giving a name," added Cavallari.

Flay hasn't commented on Handler's story.

Handler's Other "Bad" Date Story

After Cavallari pressed Handler for more celebrity dating stories, the comedian recalled another instance where things definitely didn't pan out. This time, however, she didn't name names.

"This is actually relatable. We were flirting and I made the move, I was like, I want to get in on this. I made the move, he was receptive, we were hanging out and I saw him and we went on a date and it was unbearable," she said. "Unbearable."

According to Handler, the date occurred somewhere overseas, with Chelsea stopping in the mystery man's city just so they could link up.

"He was so serious about himself as an actor and he was talking about acting in a way I could not take seriously," she explained. "I just couldn't believe how solipsistic this guy was. He didn't ask me one question about myself."

Though she said he thought the night "went great," Handler shared she felt "like I was 25 years old and had to make up a lie to get away because I had really pursued him."

"But then once I sat down with him, I was like, ‘You're so boring and you're so annoying.'"

This story was originally published by Men's Journal on May 26, 2026, where it first appeared in the Entertainment section. Add Men's Journal as a Preferred Source by clicking here.

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This story was originally published May 26, 2026 at 12:15 PM.