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.
Chelsea Handler (seen waving in 2024) recalled a “bad” dating experience she had with Bobby Flay. GC Images
The comedian said the chef (seen above holding a plate of food) offered to purchase hotel room service for her and her friends. ABC via Getty Images
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.’”
Handler (seen above in a selfie) said she was shocked to be left with the bill. chelseahandler/Instagram
The former talk show host (seen at the Kevin Hart roast in May) said someone told her Flay was “really cheap.” Getty Images for Netflix
“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.
Handler (seen above at BottleRock Napa Valley in May) said she later went on a date with the cookbook author but claimed it was “messy.” AP Photo/Amy Harris
In 2024, Flay (seen in NYC in May) claimed Kristin Cavallari rejected his flirty DM. GC Images
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 restaurateur (seen above at the 2026 South Beach Wine & Food Festival) clarified that he just wanted to take the “Hills” alum to dinner “as friends.” Getty Images
Flay is currently dating chef Brooke Williamson (seen above). GC Images
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.