Chelsea Handler details dating philosophy after bad experience with ‘a celeb’

American comedian gets honest about her worst dating story with a celebrity chef

By Madiha Akhtar May 27, 2026
Chelsea Handler details dating philosophy after bad experience with ‘a celeb’
Chelsea Handler details dating philosophy after bad experience with ‘a celeb’

Chelsea Handler recently admits she doesn’t believe in long-term relationship after her bad romantic experiences in the past.

The American comedian dishes out her dating philosophy during an appearance on Tuesday’s episode of Kristin Cavallari’s Let’s Be Honest podcast.

“I'm not interested in anything that comes after the six-month relationship mark,” says the 51-year-old, who splits from latest boyfriend and married three times over the years.

Chelsea tells Kristin, “I'm not interested in dealing with your family or your issues. I am not interested.”

The actress-comedian doesn’t want to be a part of any family unit and just wants to have “a good and sexy affair”.

“I don't want to be a couple,” declares Chelsea.

Elsewhere on the podcast, the This Means War actress recalls her bad dating experience with a celebrity chef in the past.

Chelsea says that his name is Bobby Flay, with whom she was introduced by a mutual friend.

Chelsea Handler details dating philosophy after bad experience with ‘a celeb’

“I was at a hotel with some girlfriends,” remembers the former Chelsea Lately host.

The comedian shares, “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.’”

But Chelsea claims that Bobby left her with the bill

“And I’m like, ‘What?’ And then somebody was like, ‘Oh yeah. He’s really cheap.’ And I was like, ‘Oh, I hate cheap,’” stated the actress.

Chelsea makes it clear that if a person is “penurious,” she’s not interested in them.

“I’m generous and I like people to be generous with their money,” she adds.

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