Kristin Cavallari remembers closing Bobby Flay’s dinner invitation

Kristin Cavallari had an awkward moment with Bobby Flay before they became friends.

“You and I had a situation… I literally came to Nashville for one day for a meeting. I thought, ‘Who do I know in Nashville?’ So I sent you a DM,” Flay, 59, recalled during an appearance at Cavallari’s Podcast ‘Let’s be honest’ on Tuesday, October 29. “I said, ‘I’m going to be in Nashville for one night. Can I take you out to dinner?’”

Cavallari, 37, was quick to shut him down.

“I thought, ‘I’m dating now.’ I was burned out on dating or something,” she said.

Flay remembered the Laguna Beach alum told him she was “already” seeing someone.

“I said, ‘I just want to go out to dinner with you,’” Flay continued, adding that the duo “had the best time” when they went out to dinner.

However, the entire experience became an important lesson for Flay in general.

“You taught me something I didn’t know before. You said, ‘The words you used made me feel (like it was a date)’,” the chef said. “I didn’t think about it that way.”

Cavallari admitted that she “shouldn’t just assume” that’s what Flay wanted take her on a date.

“I think the right thing to do is say, ‘Hey, I’m going to Nashville for a day.’ If you’re free, I’d like to go out for dinner,” she said, giving Flay advice on how the situation could have gone differently. “I think the ‘take you out to dinner’ thing is more like, ‘Oh, that looks like a date.'”

Flay was open to Cavallari’s advice and said “my bad” for the miscommunication.

‘Listen, we did it. It’s all good,” Cavallari said. “We ended up going out to dinner. It was fine.”

Flay further discussed how he approached dating his ex-girlfriend Christina Perez because everything now goes “via technology”.

“My ex-girlfriend, the sweetest person in the world, we were put together by a mutual friend,” he began. “I texted her and said, ‘Do you have time for a phone call?’ Some people who work for me are in their 30s and say, “That never happens, everything is always done by text message.”

Cavallari complimented Flay on his “great move”, explaining that it is a “great way to gauge a possible connection”.

Flay and Pérez were together for more than three years before People confirmed in June that they had split. Flay was previously married three times Debra Ponzek from 1991 to 1993, Kate Connelly (with whom he shares daughter Sophie Flay) from 1995 to 1998, and actress Stephanie March from 2005 to 2015. There was also a romantic connection with him Helen Yorke from 2016 to 2019.

During Tuesday’s podcast, Flay and Cavallari discussed dating at length, as the chef is back on the dating scene. (Cavallari is also single and has separated from friend Mark Estes last month.)

“I’ve been on television basically my entire adult life. So I like to keep as much as possible in my personal life to myself,” Flay admitted. “That said, it seems like there are people who are interested in what I do in my personal life. I don’t know exactly why. It’s not that exciting.”