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Chelsea Handler name-drops 'cheap' A-list chef who took h...
Tamantha Rya · 2026-05-26 · via New York Post

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 in a navy jumpsuit waves to the camera.

Chelsea Handler (seen waving in 2024) recalled a “bad” dating experience she had with Bobby Flay. GC Images

Bobby Flay holding a plate of chicken wings with cilantro and lime.

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.'”

Chelsea Handler lying in bed, smiling and wearing a t-shirt that reads "DON'T BE A LITTLE BITCH".

Handler (seen above in a selfie) said she was shocked to be left with the bill. chelseahandler/Instagram

Chelsea Handler smiling in a white strapless top and pants, with a brown background.

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

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“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.

Chelsea Handler smiling at BottleRock Napa Valley.

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

Bobby Flay leaving ABC Studio.

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.

Bobby Flay on stage during a cooking demonstration, holding a white towel in one hand and gesturing with the other.

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

Bobby Flay and Brooke Williamson pose at the US Open.

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.