Chelsea Handler and Food Network Star’s Romance That Never Was

In another time, Chelsea Handler and Bobby Flay might have supplied the Food Network with a few entertaining cameos. Despite briefly flirting with the celebrity chef, however, Handler recently revealed that the potential romance was doomed from the start—and her story makes it easy to understand why.

During a May 2026 appearance on “Let’s Be Honest with Kristin Cavallari”, Handler said mutual friends once attempted to set her up with Flay. At first, both seemed open to the idea. While Handler was staying at a hotel with friends, she and Flay had a flirty phone conversation, during which he offered to order their food. “He’s like, ‘Let me order your food for you, I love that hotel,'” Handler recalled. She agreed, thinking it might be a charming gesture from a potential love interest. The problem? Flay didn’t pay. After the meal arrived, Handler and her friends were given the bill.

The unexpected check was already a turnoff, but Handler said the situation became even worse when someone told her Flay was widely known to be “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 explained. Handler is known for supporting causes she cares about and treating loved ones to experiences such as vacations with her $35 million net worth. Flay, meanwhile, is reportedly worth nearly twice as much, at around $60 million—making the incident even less appealing to her.

The room-service mishap did not end the possibility entirely. Handler told Kristin Cavallari that she eventually went on an actual date with Bobby Flay, but the relationship still went nowhere. “It was just not a match. It was just like, it was messy. Messy,” she said with a laugh. Handler did not share additional details, though Cavallari clearly enjoyed hearing the name behind the story. “I love you for giving a name. Oh, Bobby!” she joked.

Handler had already signaled that she was perfectly comfortable identifying Flay. Before telling the room-service story, she quipped, “He’s gonna love this,” and added that he was someone she did not mind incriminating. Flay is not the only former crush she has discussed publicly. In 2020, Handler told “The View” that she had asked Andrew Cuomo out, and that he initially agreed before ghosting her. She jokingly encouraged the hosts to ask Cuomo about it when he was scheduled to appear on the show the following day. Months later, however, Handler was likely relieved they never went out. After disturbing allegations against Cuomo emerged in 2021, she said she no longer had a crush on him.

By 2026, Handler had seemingly moved on to a far better match. During an appearance on “Jimmy Kimmel Live”, the comedian revealed that she had been traveling around the world with a lover she met while gambling in Las Vegas. He had even lent her money after she ran out during the night. For anyone who believes that life has a way of working out as it should, Chelsea Handler’s romantic history offers a compelling example.