Handler doesn’t have to worry about cheap behavior from her current boyfriend, who readily gave her $1,000 when they first met.

Chelsea Handler name-drops ‘really cheap’ chef who took her on ‘pretty bad’ date: ‘It was not a match’

Handler doesn't have to worry about cheap behavior from her current boyfriend, who readily gave her $1,000 when they first met.

By Shania Russell

Shania Russell

Shania Russell is a news writer at *, *with five years of experience. Her work has previously appeared in SlashFilm and Paste Magazine.

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May 26, 2026 11:44 a.m. ET

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Chelsea Handler. Credit:

Michael Kovac/Getty

- Chelsea Handler reveals the "really cheap" celebrity chef who took her on a "pretty bad" date.

- On a new episode of the *Let's Be Honest *podcast, the comedian recounts how Bobby Flay made a bad first impression on her.

- Handler previously denied being in a relationship with Flay after the duo were photographed together in 2016.

Chelsea Handler is putting an A-list chef on blast.

The comedian has revealed the big dating faux-pas that she absolutely can't abide: a man who isn't willing to spend money. During a visit to Kristin Cavallari’s *Let’s Be Honest *podcast on Tuesday, Handler didn't hesitate to share her "bad celebrity date story," involving a certain Food Network alum who didn't impress her at dinner.

"I went on a date with Bobby Flay, that was pretty bad," Handler dished.

She explained that the duo were connected by a mutual friend and spent a while chatting in the lead-up to their date.

"We were talking on the phone [and] flirting a little bit," Handler said. "I was at a hotel with some girlfriends… He knew the hotel well and he's like — he wanted to order room service, food for us. He was like, ‘Let me order your food for you. I love that hotel.'"

Handler said the *Worst Cooks in America* alum ended up ordering food for her and three friends — but when the food arrived, the comedian was shocked to be handed the bill.

Chelsea Handler; Bobby Flay.

Michael Kovac/Getty; Jesse Grant/Getty

"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.'"

She added, "If you’re penurious, I’m not interested in you. I’m generous and I like people to be generous with their money."

Handler ultimately let the room service blindside slide and later met the chef for a dinner date, but "it was not a match."

While didn't reveal any specifics about the meal they shared, Handler laughed as she added, "It was just, like, messy."

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Handler and Flay sparked romance rumors in 2016, when they were spotted walking into a restaurant together. The buzz eventually died down and Handler addressed the whispers during a visit to the *Breakfast Club** *radio show that December, denying that they were ever a couple.

"I did not date Bobby Flay; I went on a date with Bobby Flay, one time," Handler clarified. She then admitted to feeling "short-changed" because the celebrity chef never actually cooked for her. "Is he that great of a chef that he didn't have to cook for me? F--- you, Bobby Flay!"

The same interview saw Handler dish about several of her other exes, including a two-month relationship with rapper 50 Cent.

"I liked him. He was really sweet," Handler said. "He just came after me and wouldn't let up, so I was like, 'Alright, fine.' And then I was like, 'Now go away.'"

Handler is now in a relationship with Florida construction executive Joe Largura. The couple went Instagram official in March, after Handler shared a photo dump from her recent travels, in which Largura was heavily featured.

Chelsea Handler and Joe Largura.

Chelsea Handler/Instagram

As for concerns about her new beau being cheap, Handler cleared that mystery up in their very first conversation. During a recent interview with *Las Vegas Review-Journal*, the comedian revealed that the couple met while playing blackjack in Las Vegas— during which Largura had no troubles parting with his cash.

"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," Handler told the publication of their first interaction. "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."

Handler said she won "immediately" and paid him back, with interest. The next morning, she got a mysterious text that read, "I had so much fun with you last night," only to learn that her friend had slipped Largura her number.

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Handler then invited him to join her on a vacation to Antarctica that she had already booked for Thanksgiving. "He bought a ticket and met me there," she said.

The pair ended up ringing in her 52nd birthday together under the Northern Lights.

“I’m still going strong with this guy," she said. "It’s hot, and a woman like me needs a big move like that."

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