Chelsea Handler is spilling details about a celebrity date that clearly didn’t leave a great impression.
During an appearance on Kristin Cavallari’s Let’s Be Honest podcast, the comedian opened up about a past romance attempt with a famous chef — and didn’t hold back when describing why things fizzled out.
The awkward situation reportedly started before they even went on an official date.
The Room Service Incident
Handler revealed that the celebrity chef in question was Bobby Flay.
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According to Handler, the two had been flirting after getting set up by someone when Flay offered to send food to her hotel room while she was staying there with friends.
He wanted to order food for us. He was like, ‘Let me order your food for you.’ But when the meal arrived, Handler claimed the hotel also brought her the bill.
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“And I’m like, ‘What?’” she remembered thinking. Handler said someone later told her Flay allegedly had a reputation for being “really cheap.”
Not a Fan of Cheap
The comedian admitted that the moment immediately rubbed her the wrong way.
If you’re penurious [stingy], I’m not interested in you. I’m generous, and I like people to be generous with their money.
Despite the awkward start, Handler said the two eventually went on a real date — though it apparently didn’t improve things much.
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“It was not a match,” she said, later adding that the situation was simply “messy.”
Bobby Flay Previously Appeared on the Podcast
Flay also appeared on Cavallari’s podcast in 2024, where he recalled unsuccessfully trying to ask The Hills alum out on a date by sliding into her DMs.
Flay is currently in a relationship with fellow chef Brooke Williamson.
Celebrities Who Slid Into DMs
From Lizzo to Dua Lipa and Joe Jonas, check out stars who slid into other peoples’ DMs.
Gallery Credit: Donny Meacham