Chelsea Handler says a mutual friend set her up with Bobby Flay, but a room-service plan turned into an awkward “cheap” bill moment—followed by another messy date that wasn’t a match.
Chelsea Handler still sounds like she remembers every detail.
On Kristin Cavallari’s “Let’s Be Honest” podcast, the comedian was asked about a “bad celebrity date story” she hadn’t told before. Handler didn’t pause. “Yeah, I went on a date with Bobby Flay. That was pretty bad.”
The setup, Handler said, came from a mutual friend who “hooked [her] up.” She and Flay started “talking on the phone” and “flirting a little bit” before it ever turned into an actual hangout.
Then came the night itself. Handler said she was at a hotel with her girlfriends when Flay offered to order them room service. In Handler’s telling, he knew the hotel well and leaned into it, saying, “Let me order your food for you. I love that hotel… I’m going to order it.”
It should’ve been a smooth move. Instead, it landed like a trap—at least to Handler. She recalled that after the meal, they brought her the bill, and she was left staring at it thinking, “What is this guy?”
Handler said the explanation arrived fast, too. A friend told her, “Oh yeah, he’s really cheap. He’s really cheap,” and Handler made her position unmistakable. “I hate cheap.”
She added, “If you’re penurious, I’m not interested in you. I’m generous, and I like people to be generous with their money.”
Even with that room-service incident in the rearview, Handler and Flay did end up going on a date. That one, she said, still didn’t click. “It was just not a match. It was just, like, messy,” she told Cavallari.
The conversation also touched on Handler’s current relationship philosophy. She talked about being single at 51 and said she prefers short flings over 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.
Handler went further about what she does and doesn’t want. explaining. “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 Bobby Flay, he’s not single these days—he’s currently dating Food Network star Brooke Williamson. Handler’s story may have ended in messy disappointment for her, but for Flay, the timeline has moved on: he and Williamson have been together since early 2025.
Chelsea Handler Bobby Flay Kristin Cavallari Let’s Be Honest podcast room service bill Brooke Williamson Food Network celebrity dating