Chelsea Handler isn’t shying away from spilling the details of a disappointing date she clearly hasn’t forgotten. During her latest appearance on Kristin Cavallari’s “Let’s Be Honest” podcast, Handler was asked about a “bad celebrity date story” she hadn’t told before. Without hesitation, the comedian responded, “Yeah, I went on a date with Bobby Flay....
Chelsea Handler isn’t shying away from spilling the details of a disappointing date she clearly hasn’t forgotten.
During her latest appearance on Kristin Cavallari’s “Let’s Be Honest” podcast, Handler was asked about a “bad celebrity date story” she hadn’t told before. Without hesitation, the comedian responded, “Yeah, I went on a date with Bobby Flay. That was pretty bad.”
According to Handler, a mutual friend “hooked [her] up” with the chef, and the two started “talking on the phone” and “flirting a little bit” before disaster struck. Handler recalled that she was at a hotel with her girlfriends when Flay offered to order them room service, but things went south shortly after.
“He knew the hotel well… He wanted to order room service food for us. He was like, ‘Let me order your food for you. I love that hotel… I’m going to order it,’” Handler told Cavallari, adding, “But then they brought me the bill, and I’m like, ‘What is this guy?’”
“And then [a friend of mine] was like, ‘Oh yeah, he’s really cheap. He’s really cheap,'” she said before making it clear that she “hates cheap.”
She noted, “If you’re penurious, I’m not interested in you. I’m generous, and I like people to be generous with their money.”
Handler and Flay did end up going on a date after the room service incident, but that fell short of expectations as well. “It was just not a match. It was just, like, messy,” the starlet said.
Handler also talked about being single at 51. She explained that she’d rather entertain short flings than long-term commitment. “I am not a long-term person. I just am not interested in anything that comes after the six-month relationship mark,” she said.
She further justified her choice, saying, “I’m not interested in dealing with your family or your issues… Maybe that will change, but I’m not at a place in my life where I want to take on another person’s [issues]… I want to have a good, s*** affair. I don’t want to be a couple. I just want to have somebody that I’m into and buzzing on.”
As for Flay, he is currently dating Food Network star, Brooke Williamson. The two have been together since early 2025.
