Chelsea Handler didn’t hold back when it came to her dating history.
The comedian revealed on Kristin Cavallari’s Let’s Be Honest podcast that she once had a “bad” date with celebrity chef Bobby Flay.
Handler explained that the two were introduced through mutual friends and began chatting on the phone.
Their flirtation led to Flay offering to order room service for Handler and her girlfriends while they were staying at a hotel he knew well.
“He wanted to order food for us,” Handler recalled. “He was like, ‘Let me order your food for you. I love that hotel.’”
But when the food arrived, Handler said she was shocked to be handed the bill.
“And I’m like, ‘What?’” she remembered. “Then somebody was like, ‘Oh yeah. He’s really cheap.’ And I was like, ‘Oh, I hate cheap.’”
Despite the awkward start, Handler did go on a date with the Beat Bobby Flay star, but she admitted it was “not a match,” describing the experience as “messy.”
Handler, known for her blunt humor, added, “If you’re penurious, I’m not interested in you. I’m generous and I like people to be generous with their money.”
The revelation came after Flay himself appeared on Cavallari’s podcast in 2024, where he admitted she once rejected his flirty DMs.
At the time, he clarified he only wanted to meet her for dinner “as friends.”
Currently, Flay is in a relationship with fellow chef Brooke Williamson, while Handler continues to share her unfiltered takes on love and life with fans.
2026-05-26 20:11:00
