NEWSChelsea Handler Drags 'Cheap' Bobby Flay for Being One of Her Worst Celebrity Dates: 'It Was Not a Match'
'I’m generous and I like people to be generous with their money,' Chelsea Handler expressed.
May 26 2026, Published 10:43 a.m. ET
Chelsea Handler spilled the tea on the awkward experience she had with Bobby Flay.
The comedian dished about their connection on the Tuesday, May 26, episode of Kristin Cavallari's "Let's Be Honest" podcast when the host asked about any "bad" celebrity dates she's been on.
Chelsea Handler and Bobby Flay Flirted Before They Went Out
Chelsea Handler named Bobby Flay when asked to share a 'bad' date story.
Handler, 51, revealed someone once got her and Flay, 61, in touch, and the two started "talking on the phone [and] flirting a little bit."
At the time, she was staying at a hotel with some friends, and since the chef "knew the hotel well... he was like, ‘Let me order your food for you. I love that hotel.'"
However, when the food arrived, so did the check, and the comic had to pay for everything the Beat Bobby Flay star ordered.
'It Was Not a Match'
The chef ordered Chelsea Handler and her friends room service but made the comedian pay the bill.
"And I’m like, ‘What?' And then somebody was like, ‘Oh yeah. He’s really cheap,’" Handler recalled. "And I was like, ‘Oh, I hate cheap.'"
"If you’re penurious, I’m not interested in you. I’m generous and I like people to be generous with their money," she explained.
Handler wound up giving him a second chance and the two went out in-person, but "it was not a match. It was just like, messy," she said.
Handler is currently single but recently raved over a romance she had with a younger guy.
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Bobby Flay Once Took Kristin Cavallari Out to Dinner
Kristin Cavallari initially shut down Bobby Flat when he invited her to get dinner in Nashville, Tenn.
Funny enough, Cavallari, 39, had her own experience with the father-of-one, which they discussed when he appeared on her podcast in 2024.
"I DMed you and I said to you … ‘I’m going to be in Nashville for one night, can I take you to dinner?' And you literally said something to me like, ‘I’m already dating somebody,’" he recalled, to which the reality star replied, "Or I was like, ‘I’m over dating right now.’ I was burnt out on dating or something.”
The Pair Had 'the Best Time'
The reality star admitted she assumed Bobby Flay was asking her out in a romantic way when she first declined.
"No, you said, ‘I’ve already started seeing somebody!’ And I said, ‘I just want to go to dinner with you,’” he continued.
"It was like foot in mouth," the mom-of-three confessed, admitting she assumed the Food Network star meant for it to be a romantic outing. "I think the ‘take you to dinner’ thing is more where it was like, ‘Oh, that seems like a date.'"
The two ended up going on a platonic dinner date, with the podcast host revealing she had "the best time."
