Did Bobby Flay Ask Kristin Cavallari On A Date? Inside The Silly Mix-Up

Bobby Flay hasn't had the best luck when it comes to romance. The celebrity chef has been married three times and has an extensive dating history that includes relationships with high-profile celebrities like actress Helene Yorke and a rumored romance with his Food Network co-host Giada De Laurentiis. Flay also once went on a date with comedian Chelsea Handler, who hilariously called him out when he didn't cook for her. In a hilarious mixup, "Laguna Beach" alum Kristin Cavallari turned him down for a date, even though he wasn't interested in her like that.

During an appearance on Cavallari's "Let's Be Honest" podcast in October 2024, Flay brought up an old DM exchange between the pair that they both seemingly misread. At the time, Flay was in Nashville for work, where Cavallari has real estate, and wanted to get dinner with someone. "So, I DM'd you," he said, recounting that he wrote: "I'm going to be in Nashville for one night. Can I take you to dinner?" In his mind, he thought he was just asking a friend to dinner. But, Cavallari read it differently and responded with, "'I literally started seeing somebody" per Flay. Addressing the past interaction, Cavallari agreed that "I shouldn't just assume that you wanted to take me on a date," but added "The 'take you to dinner' feels like a date." The good news is they did eventually go to dinner as friends and "had the best time," according to Cavallari.

Bobby Flay's botched dinner attempt with Kristin Cavallari seemingly taught him to be more mindful about the language he uses when messaging a woman. His three marriages also taught him an important lesson — that marriage is no longer his end goal. On the same episode of "Let's Be Honest," Cavallari pressed him as to whether "marriage was off the table" for him, to which he responded, "Probably, yes," later adding that "it hasn't been the best situation." Flay explained that he "would be interested in a life partner for sure" but didn't think it needed documentation: "Once you sign a document that says, 'You are now together,' there's something that changes," he said. 

Flay hasn't been married since 2015, when he and his third wife Stephanie March reached a divorce settlement. Since then, he dated Helene Yorke from 2016 to 2019 and Christina Perez from 2021 to 2024. Following his breakup with Perez, he told People in July 2024 that he was just taking it easy. "I'm just relaxed right now," he said when asked if was starting to date again. "I mean, I don't really have anything to say about that. It's still kind of new for me."