Latest Shocking Entertainment News: Chelsea Handler Claims Bobby Flay Left Her With the Bill After Date

Chelsea Handler is recalling her one memorable encounter with Bobby Flay.

“Yeah, I went on a date with Bobby Flay. That was pretty bad,” Handler, 51, said on the Tuesday, May 26, episode of the “Let’s Be Honest” podcast, after host Kristin Cavallari asked if she had a “bad celebrity date story” to share.

Handler continued, “It was just bad. Everything. He ordered me room service. So we were talking — someone hooked us up —- we were talking on the phone, flirting a little bit. I was at a hotel with some girlfriends. I think we were filming for Netflix.”

Handler recalled that the pair were somewhere in the United States, noting that Flay “knew the hotel well.”

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“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.’ Maybe it was Vegas or something. I usually can remember these details. Anyway, he orders me food. He’s going to love this. This is somebody I don’t mind incriminating,” he said. “Three of my girls are in the room with me and he’s like, ‘I’m going to order it.’”

She continued, “But then they brought me the bill. And I’m like, ‘What is this guy?’ And then somebody was like, ‘Oh yeah, he’s really cheap. He’s really cheap.’ And I was like, ‘Oh, I hate cheap.’ … I’m generous and I like people to be generous with their money.”

The pair ultimately went on another date, but Handler did not feel like it went well.

“We did end up going on a date and it was just not a match,” she said. “It was just messy.”

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Us Weekly reached out to Flay’s team for comment.

Handler, for her part, is currently dating a mystery man. In March, the comedian shared a glimpse of the pair’s travels together and shared that they met while sitting at a blackjack table at The Cosmopolitan in Vegas in November 2025.

Flay, 61, has been in a relationship with Top Chef winner Brooke Williamson since 2025. He was previously married to Debra Ponzek from 1991 to 1993, Kate Connelly from 1995 to 1998 and Stephanie March from 2005 to 2015. He shares his daughter, Sophie, with Connelly.

While Flay and Williamson have sparked engagement rumors after she was spotted wearing a ring in 2025, he has denied the idea.

“It’s a commitment ring. I’m not engaged,” Bobby clarified during a November 2025 appearance on Elvis Duran and the Morning Show. “We both don’t want to get married again. It’s OK. So, like, it’s great having a life partner. And so I wanted to give her something significant to make her feel committed. That’s all.”

by Ryan Hudgins

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