When Let’s Be Honest podcast host Kristin Cavallari asked Handler, 51, to share a “bad celebrity date story” that she hasn’t told before, the comedian immediately named Flay. After “someone hooked [them] up,” the duo “were talking on the phone [and] flirting a little bit,” which led to Flay ordering Handler room service, reports Page Six. “I was at a hotel with some girlfriends,” the comedian recalled. “He knew the hotel well. He wanted to order … food for us. He was like, ‘Let me
order your food for you. I love that hotel’”. Handler claimed Flay, 61, ordered the food — but the hotel brought her the bill. “And I’m like, ‘What?’” she remembered thinking. “And then somebody was like, ‘Oh yeah. He’s really cheap.’ 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,” Handler shared. Despite the food service blunder, Handler later went on a date with the Beat
Bobby Flay star, but “it was not a match”. Handler did not elaborate further, simply saying, “It was just like, messy”. Page Six has reached out to Flay’s spokesman for comment but did not immediately hear back. In November 2024, Flay revealed on Cavallari’s podcast that she once rejected his flirty messages. “I DMed you and I said to you … ‘I’m going to be in Nashville for one night. Can I take you to dinner?’” he said at the time. “And you literally said
something to me like, ‘I’m already dating somebody,’” Flay recalled. The Hills star, 39, claimed she actually responded by saying she was “burnt out” with dating — but Flay doubled down. “No, you said, ‘I’ve already started seeing somebody!’ And I said, ‘I just want to go to dinner with you,’” he replied with a laugh, explaining that he just wanted to meet up as friends. The cookbook author is currently in a relationship with fellow chef Brooke Williamson. This article originally appeared in Page
Six and was reproduced with permission.
Chelsea Handler, Beat Bobby Flay, Kristin Cavallari, Let’s Be Honest, bad date, room service bill, Brooke Williamson, The Hills