Worst date in America?
Chelsea Handler spilled the tea on her “bad” dating experience with celebrity chef Bobby Flay during Kristin Cavallari’s “Let’s Be Honest” podcast Tuesday.
When the host asked Handler, 51, to share a “bad celebrity date story” that she hasn’t told before, the comedian immediately named Flay.
After “someone hooked [them] up,” the duo “were talking on the phone [and] flirting a little bit,” which led to Flay ordering Handler room service.
“I was at a hotel with some girlfriends,” the “Chelsea Lately” alum recalled. “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.’”
Handler claimed Flay, 61, ordered the food — but the hotel brought her the bill.
“And I’m like, ‘What?’” she remembered thinking. “And then somebody was like, ‘Oh yeah. 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,” Handler shared.
Despite the food service blunder, Handler later went on a date with the “Beat Bobby Flay” star, but “it was not a match.”
Handler did not elaborate further, simply saying, “It was just like, messy.”
Page Six has reached out to Flay’s rep for comment but did not immediately hear back.
In November 2024, Flay revealed on Cavallari’s podcast that she once rejected his flirty messages.
“I DMed you and I said to you … ‘I’m going to be in Nashville for one night. Can I take you to dinner?’” he said at the time.
“And you literally said something to me like, ‘I’m already dating somebody,’” Flay recalled.
The “Hills” alum, 39, claimed she actually responded by saying she was “burnt out” with dating — but Flay doubled down.
“No, you said, ‘I’ve already started seeing somebody!’ And I said, ‘I just want to go to dinner with you,’” he replied with a laugh, explaining that he just wanted to meet up as friends.
The cookbook author is currently in a relationship with fellow chef Brooke Williamson.
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