The Story Behind Chelsea Handler's 'Bad' Date With Bobby Flay

Bobby Flay may have no intention of getting married again, but the chef seems pretty happy with his current girlfriend and fellow chef, Brooke Williamson. Flay hasn't always been so lucky in love, and he definitely didn't hit it off with Chelsea Handler. The quick-witted comedian had some not-so-nice things to say about the chef on the "Let's Be Honest with Kristin Cavallari" podcast, her main complaint being his frugality. 

According to Handler, a telephone flirtation between the two celebrities escalated when Flay offered to remotely order Handler and her friends room service at their hotel. Emphasis on the word "ordered." The comedian was given a check for the food when she assumed that Flay would be footing the bill. Handler says someone then informed her that Flay was "really cheap," which didn't sit right. Despite the snag, Handler agreed to a real date with Flay, a rendezvous she ultimately characterized as "messy," saying, "It was not a match." Flay has yet to comment on the date, so there's no telling whether he'll take Handler's humorous anecdote in stride. 

Despite his success in the culinary world, Bobby Flay is no stranger to scandals. His divorce from actress Stephanie March in 2015 was particularly volatile — March alleged the chef had cheated and sought to undo a prenuptial agreement established at the beginning of the marriage. The chef was also married two other times, which likely influenced his current opinions about the unnecessary-ness of wedded bliss. He dated a few people in the public eye after his split with March, until his most recent partnership with Brooke Williamson. Flay hand-selected Williamson for "Bobby's Triple Threat", a cooking competition show that aired in 2022. The couple went public with their relationship in March 2025. 

As for Chelsea Handler, it seems her pairing with the celebrity chef was just a fundamental mismatch where money was concerned. On "Let's Be Honest with Kristin Cavallari," Handler said, "I'm generous, and I like people to be generous with their money." The comedian also explained that finding a committed partnership wasn't a priority in her life. The star admitted, "I don't want to be part of a unit. I want to have a good, sexy affair."