Chelsea Handler did not hesitate to name the celebrity date who made her pay for her own meal.
The comedian appeared on the Let’s Be Honest podcast with Kristin Cavallari on Tuesday, where she blasted Emmy-winning TV chef Bobby Flay when asked to share a “bad celebrity date story.” Handler, 51, told Cavallari, “I was at a hotel with some girlfriends,” when she and Flay, 61, were getting to know each other. “Someone hooked us up,” she said.
“And he’s like, ‘Oh my God,’ he wanted to order me room service, food for us. He’s like, ‘Let me order your food for you. I love that hotel.’” That was when things went downhill, she said. “He ordered me food, to, like three of my girlfriends are in the room with me, and they ordered room service. He’s like, ‘I’m going to order it.’”
“But then they brought me the bill,” she continued. “And I’m like, what?”
In the aftermath, Handler said she heard that the move wasn’t out of character for Flay. “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,” Handler added. “I’m generous. And I like people to be generous with their money. And then we did end up going on a date, and it’s not a match.”
The Daily Beast has reached out to Flay’s representative for comment.
Handler added that she had no qualms about outing Flay. “This is somebody I don’t mind incriminating,” she told Cavallari.
Flay is currently dating fellow Food Network star Brooke Williamson, 47, with whom he co-starred on Bobby’s Triple Threat. The pair, who began dating in March 2025, are a “permanent couple,” Flay said in January on his Bobby on the Beat podcast, as he explained why they decided not to marry.
“We both don’t want to get married again,” he also said in November on the Elvis Duran and the Morning Show.
Handler, who previously dated rapper 50 Cent and comedian Jo Koy, revealed a new relationship in March by making things Instagram official with her unnamed beau, whom she met in November 2025. She told the Las Vegas Review-Journal that his generosity had piqued her interest in him.
“I had to ask this guy sitting at a blackjack table who was wearing a cowboy hat, he had a lot of chips, like, thousands of dollars,” she said, recalling how they met. “I was like, ‘Hey, buddy, can I borrow $1,000? I’m gonna start winning right away. And he was like, ‘Yeah, absolutely!’ So he gave me $1,000.”
When she started winning right away, Handler said she “paid him back another thousand just for interest.”
Handler said Tuesday that posting her dating partner online does not mean she is in it for the long haul. “Listen, me being public with men is—I post guys all the time that I’m dating. I’m not posting them saying, ‘This is my boyfriend.’ It’s like who I’m spending time with. It’s reflective of whoever I’m hanging out with at the time."
She concluded, “I am not a long-term person. I just am not interested in anything that comes after the six-month relationship mark.”
