Worst date in America?
Chelsea Handler spilled the tea about her “bad” dating experience with celebrity chef Bobby Flay on Kristin Cavallari’s “Let’s Be Honest” podcast on Tuesday.
When the host asked Handler, 51, to share a previously untold “famous bad date story,” the comedian quickly mentioned Frey’s name.
After “someone called,” the two were “talking on the phone (and) were making out a little bit,” and Frey ordered room service for Handler.
“I was in a hotel with some girlfriends,” the “Chelsea Lately” alum recalled. “He knew the hotel really well. He wanted to order food for us. He was like, ‘Let me order food. I love that hotel.'”
Handler claimed Frey, 61, ordered food, but the hotel brought him the bill.
“And I was like, ‘What?'” she remembers thinking. “Then someone said, ‘Oh yeah, he’s really cheap.'” And I thought, ‘Oh, I hate cheap stuff.’ ”
“If you’re poor, I don’t care about you. I’m generous, so I like it when people are generous with their money,” Handler said.
Despite her failure in food service, Handler later went on a date with the “Beat Bobby Flay” star, but “it just wasn’t a good fit.”
Handler didn’t elaborate further, only saying, “It was just a mess.”
Page Six reached out to Frey’s representatives for comment, but did not immediately receive a response.
In November 2024, Frey revealed on Cavallari’s podcast that she once rejected his flirtatious messages.
“I DMed you and said…’I’m going to be in Nashville for the night. Can I take you out to dinner?'” he said at the time.
“And you literally said something to me like, ‘I’m already dating someone,'” Frey recalled.
The 39-year-old “Hills” alum claimed she actually reacted by saying she was “burnt out” on the date, but Frey doubled down.
“No, you said, ‘I’m already dating someone!’ So I said, ‘I just want to go out to dinner with you,'” he replied with a laugh, explaining that he just wanted to meet as friends.
The cookbook author is currently dating fellow chef Brooke Williamson.
