What Could Have Been: Chelsea Handler & This Food Network Star's Doomed Connection

In another place and time, we might have gotten a few good Chelsea Handler cameos on the Food Network. JK, despite flirting with Bobby Flay at one point, Handler revealed that they were doomed right from the get-go, and we definitely see why she felt that way. 

When Handler appeared on "Let's Be Honest with Kristin Cavallari" in May 2026, she revealed that at some point, mutual friends tried to get her and Flay together. It seems as though initially both of them were kind of into it, and she shared that at one point while she was at a hotel with friends, they were having a flirty phone conversation, and he decided to flex his food knowledge on her. "He's like, 'Let me order your food for you, I love that hotel,'" Handler recounted. She agreed, and TBH, that could have been a great way to make a good impression on a potential love interest. That is, if he'd paid. However, he didn't, and after the food he'd ordered for Handler and her friends arrived, they handed her the bill. Smooth, Flay. Real smooth. 

While that would probably be a turn-off for most people, Handler added that what made it worse was someone telling her it was well-known that he was "cheap." "I was like, 'Oh, I hate cheap.' Like ... if you're penurious, I'm not interested in you. I'm generous, and I like people to be generous with their money," she said. Sure enough, Handler is known to donate generously to causes close to her heart and is partial to treating her loved ones to things like vacations with her $35 million net worth,  so given that Flay is said to be worth nearly double that at $60 million ... we don't blame her for getting the ick. 

Despite the disastrous room service debacle, Chelsea Handler told Kristin Cavallari that she did end up going out with Bobby Flay at a later date anyway. However, let's just say things didn't fare much better. "It was just not a match. It was just like, it was messy. Messy," she laughed. Handler didn't offer further details, but evidently putting his name out there hadn't been something Cavallari expected, because she laughed, "I love you for giving a name. Oh, Bobby!"

Well, for what it's worth, Handler had said earlier on in the conversation that she had no problem name-dropping him. At the start of the room service story, she'd quipped, "He's gonna love this," before making it clear she wasn't bothered either way. "This is somebody I don't mind incriminating," she joked. Of course, Flay isn't the only former crush Handler has called out. Some may remember that in 2020 she told "The View" she'd asked Andrew Cuomo out and that he'd agreed ... and then ghosted her. Handler jokingly asked the hosts to ask Cuomo about it, as he was scheduled to appear on the show the very next day, but a few months later, it's safe to say she was pretty glad they never did go out. In 2021, after disturbing allegations about Cuomo surfaced, Handler declared that she no longer had a crush on him. 

Fast-forward to 2026, and the comedian revealed on "Jimmy Kimmel Live" that she'd been traveling the world with a lover, whom she met while gambling one night in Vegas, and who had helpfully given her money when she'd run out. Anyone who doubts the cliché that things work out exactly as they're meant to, we give you Chelsea Handler.