Chelsea Handler has recalled her brief romantic entanglement with a celebrity chef whom she described as “cheap.”
Speaking on Tuesday’s episode of Kristin Cavallari’s Let’s Be Honest podcast, the comedian, 51, was asked to share a never-before-told “bad celebrity date story.”
Handler immediately named Iron Chef America star Bobby Flay, revealing they had been introduced by a mutual friend and “were talking on the phone [and] flirting a little bit.”
“I was at a hotel with some girlfriends,” the former Chelsea Lately host remembered. “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.’”
She claimed that Flay, 61, ordered the food, but then left her with the bill.

“And I’m like, ‘What?’” Handler continued. “And then somebody was like, ‘Oh yeah. He’s really cheap.’ And I was like, ‘Oh, I hate cheap.’”
She added: “If you’re penurious, I’m not interested in you. I’m generous and I like people to be generous with their money.”
Despite the food service debacle, the pair later went on a date. However, according to Handler, they were “not a match.”
“It was just like, messy,” she said, without providing any other details.
The Independent has contacted Flay’s representative for comment.
Flay has been married three times: first to fellow chef Debra Ponzek from 1991 to 1993; then to TV host Kate Connelly — with whom he shares his only child, 30-year-old daughter Sophie — from 1995 to 1998; and later to Law & Order: SVU star Stephanie March from 2005 to 2015.
He is currently dating chef and restaurateur Brooke Williamson, 47, whom he’s been with since March 2025.

Months before reports of Flay and Williamson’s relationship broke, the chef appeared on Cavallari’s podcast, recounting the time he asked her if he could take her to dinner, only for her to turn him down.
“I DMed you and I said to you … ‘I’m going to be in Nashville for one night, can I take you to dinner?’” the Beat Bobby Flay star said. “And you literally said something to me like, ‘I’m already dating somebody.’”
Cavallari remembered the interaction differently, insisting she gave a different reason. “Or I was like, ‘I’m over dating right now.’ I was burnt out on dating or something,” she said.
Flay disagreed, arguing: “No, you said, ‘I’ve already started seeing somebody!’ And I said, ‘I just want to go to dinner with you.’”
He further shared his preference for a long-term partner rather than another marriage. “I would be interested in a life partner for sure. But I don’t think it necessarily needs the documentation,” Flay said.
Admitting that marriage “hasn’t been the best situation,” he reiterated, “I don’t feel like I need to do it again.”
