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Chelsea Handler Calls Bobby Flay Date Messy on Podcast

Published 27 May 2026

Comedian Chelsea Handler has described a past encounter with celebrity chef Bobby Flay as a "messy" and unsuccessful dating experience, citing an awkward incident involving a hotel room service bill. Handler shared the story during a recent appearance on Kristin Cavallari's "Let's Be Honest" podcast.

According to Handler, the two were introduced by a mutual friend and began talking on the phone. While she was at a hotel with friends, Flay, who said he knew the hotel well, offered to order food for the group. Handler said the gesture initially seemed promising, but the situation changed when the hotel delivered the meal along with a bill addressed to her.

Handler recalled her surprise at receiving the charge. She said someone present then remarked that Flay had a reputation for being "really cheap." The comedian stated that frugality is a deal-breaker for her, saying, "If you're penurious, I'm not interested in you. I'm generous, and I like people to be generous with their money."

Despite this initial friction, Handler said the pair proceeded to go on a formal date. She characterized the outing bluntly, stating, "It was not a match," and summarized the entire experience as "just,...

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