Worst date in America?
Chelsea Handler recalled a “bad” dating experience she had with celebrity chef Bobby Flay.
During an appearance on Kristin Cavallari’s “Let’s Be Honest” podcast Tuesday, the former reality star asked the comedian to share a “bad celebrity date story” that she hasn’t told before.
“Yeah, I went on a date with Bobby Flay. That was pretty bad,” Handler, 51, claimed.
“He ordered me room service. So, we were talking — someone hooked us up — we were talking on the phone, flirting a little bit,” the “Chelsea Lately” alum added.
“I was at a hotel with some girlfriends … he knew the hotel well. He wanted to order me room service, food for us. He’s like, ‘Let me order your food for you. I love that hotel.’”
Handler said Flay, 61, ordered their food but the hotel ended up bringing her the bill.
“And I’m like, ‘What?’ And then somebody was like, ‘Oh yeah. He’s really cheap.’ And I was like, ‘Oh, I hate cheap,’” she recalled.
“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 said she later went on a date with the “Beat Bobby Flay” star.
“Then we did end up going on a date … it was not a match,” she said, adding, “It was just like, messy.”
In November 2024, Flay revealed on Cavallari’s podcast that she 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 “Hils” alum, 39, claimed she actually responded by saying that 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.
