Chelsea Handler has publicly recounted a disappointing date with celebrity chef Bobby Flay, labeling him as cheap and declaring they were not a match. The comedian made the revelation during an appearance on Kristin Cavallari's podcast "Let's Be Honest" on Tuesday.
Room Service Incident
Handler explained that she and Flay were set up by a mutual friend and had been talking on the phone prior to their date. During one conversation, Flay offered to order room service for Handler and her friends at a hotel he knew well. However, when the food arrived, Handler was handed the bill.
"I'm like, 'What?'" Handler recalled. She added that someone then told her, "Oh yeah. He's really cheap." Handler responded, "If you're penurious, I'm not interested in you. I'm generous and I like people to be generous with their money."
Date Was Not a Match
Despite the room service incident, Handler still went on the date with Flay, but she described it as "messy" and concluded, "It was not a match." She did not provide further details about the date itself.
Handler had previously addressed the dating rumors in December 2016 on the Breakfast Club radio show, stating, "I did not date Bobby Flay; I went on a date with Bobby Flay, one time." She also expressed frustration that Flay never cooked for her, saying, "Is he that great of a chef that he didn't have to cook for me? F*** you, Bobby Flay!"
Cavallari Also Rejected Flay
Interestingly, Kristin Cavallari herself had previously turned down Flay. In November 2024, Flay appeared on Cavallari's podcast and recounted how he had messaged her to ask for a dinner date, but she declined, saying she was already seeing someone or burnt out from dating.
Handler did not specify when her date with Flay occurred, but the pair sparked dating rumors in 2016 when they were seen entering a restaurant together. Flay has since been in a relationship with chef Brooke Williamson since March 2025, while Handler went Instagram official with Florida construction executive Joe Largura in March 2026.
