Bobby Flay & Kristin Cavallari Had Awkward DM Dating Encounter – Here’s What Went Down

Celebrity chef Bobby Flay and Laguna Beach alum Kristin Cavallari have been reminiscing about an embarrassing situation regarding DMs and a dating mix-up.

Flay appeared on Cavallari’s Let’s Be Honest podcast on Tuesday, October 29, where he recalled messaging the reality star online to ask if he could take her out to dinner. This led to Cavallari rejecting Flay as she assumed he was asking her out on a date.

“I DMed you and I said to you… ‘I’m going to be in Nashville for one night, can I take you to dinner?’” Flay shared. “And you literally said something to me like, ‘I’m already dating somebody.'”

Cavallari remembered it differently, explaining, “Or I was like, ‘I’m over dating right now.’ I was burnt out on dating or something.”

Flay, however, was certain on what The Hills star said. “No, you said, ‘I’ve already started seeing somebody!’ And I said, ‘I just want to go to dinner with you!'”

Cavallari admitted it was a “foot in mouth” moment and said she shouldn’t have assumed Flay was asking her out on a date. “I think the ‘take you to dinner’ thing is more where it was like, “Oh, that seems like a date,'” she stated.

Despite the cringe-worthy mix-up, Cavallari said she and Flay eventually met up and had “the best time.”

Cavallari was previously married to Chicago Bears quarterback Jay Cutler from 2013 to 2020. The former couple share three children. More recently, the Very Cavallari star dated TikTok star and Montana Boyz member Mark Estes; however, the pair broke up in September due to concerns with their 13-year age gap.

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Meanwhile, People reported that Flay separated from his girlfriend of three years, Christina Pérez, in July. The Food Network star has been married three times: to Debra Ponzek from 1991 to 1993, to Kate Connelly from 1995 to 1998, and to actress Stephanie March from 2005 to 2015. He shares a daughter with Connelly.

When Cavallari asked Flay if marriage is “off the table completely,” he replied, “Is it off the table? If you asked me today, I’d say probably, yes. I don’t know.”

He continued, “For me, it hasn’t been the best situation. That said, I don’t feel like I need to do it again. I have an amazing daughter who is 28 years old. I’m not having any more kids as far as I know.”

However, he admitted he “would be interested in a life partner. But I don’t think it necessarily needs the documentation.”