Chelsea Handler has opened up about a brief romantic encounter with celebrity chef Bobby Flay, whom she described as "cheap." The comedian, 51, shared the story during an appearance on Kristin Cavallari's Let's Be Honest podcast on Tuesday.
When asked for a never-before-told "bad celebrity date story," Handler immediately named the Iron Chef America star. She revealed that a mutual friend had introduced them, and they had been "talking on the phone [and] flirting a little bit."
Handler recalled that she was staying at a hotel with some girlfriends when Flay offered to order food for them. "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,'" the former Chelsea Lately host said.
However, after Flay ordered the food, he allegedly left Handler with the bill. "And I'm like, 'What?'" she continued. "And then somebody was like, 'Oh yeah. He's really cheap.' And I was like, 'Oh, I hate cheap.'"
Handler 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, but Handler said they were "not a match." "It was just like, messy," she said without elaborating. The Independent has contacted Flay's representative for comment.
Flay, 61, has been married three times: to chef Debra Ponzek (1991-1993), TV host Kate Connelly (1995-1998), and Law & Order: SVU star Stephanie March (2005-2015). He shares a daughter, Sophie, 30, with Connelly. Flay is currently dating chef and restaurateur Brooke Williamson, 47, since March 2025.
Months before his relationship with Williamson became public, Flay appeared on Cavallari's podcast and recounted how he had asked her to dinner via DM, but she turned 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 recalled the interaction differently, insisting she said she was "over dating right now" or "burnt out on dating." Flay disagreed, saying, "No, you said, 'I've already started seeing somebody!' And I said, 'I just want to go to dinner with you.'"
Flay also shared his preference for a life partner over another marriage. "I would be interested in a life partner for sure. But I don't think it necessarily needs the documentation," he said, admitting that marriage "hasn't been the best situation."
