Kristin Cavallari had an awkward moment with Bobby Flay before they became friends.
“You and I had a situation … I was coming to Nashville literally for one day for a meeting. I was like, ‘Who do I know in Nashville?’ So, I DM’d you,” Flay, 59, recalled during an appearance on Cavallari’s “Let’s Be Honest” podcast on Tuesday, October 29. “I said, ‘I’m going to be in Nashville for one night. Can I take you to dinner?’”
Cavallari, 37, was quick to shut him down.
“I was like, ‘I’m over dating right now.’ I was burnt out on dating or something,” she said.
Flay remembered the Laguna Beach alum telling him that she was “already” seeing someone.
“I said, ‘I just want to go to dinner with you,’” Flay continued, adding that the duo “had the best time” when they did go out to eat.
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However, the entire experience became an important lesson for Flay overall.
“You taught me something I didn’t know. You said, ‘The words that you used made me feel [like it was a date],’” the chef said. “I didn’t think of it that way.”
Cavallari did admit that she “shouldn’t just assume” that Flay wanted to take her out on a date.
“I guess the right thing to do is say, ‘Hey, I’m going to be in Nashville for a day. If you’re free, I’d love to go to dinner,’” she said, offering Flay advice about how the situation could have gone differently. “I think the ‘take you to dinner’ thing is more where it was like, ‘Oh, that seems like a date.’”
Flay was receptive to Cavallari’s advice, saying “my bad” for the miscommunication.
“Listen, it worked out. It’s all good,” Cavallari said. “We ended up going to dinner. It was fine.”
Flay went on to discuss how he approached dating ex-girlfriend Christina Pérez because everything is “through technology” now.
“My ex-girlfriend, who is the loveliest person in the world, we were put together by a mutual friend,” he started. “I texted her and I said, ‘Do you have time for a call?’ Some of the people that work for me are in their 30s, and they’re like, ‘That never happens, everything is always by text.’”
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Cavallari complimented Flay for his “great move,” explaining that it’s a “great way to gauge” a possible connection.
Flay and Pérez were together for more than three years before People confirmed in June they had split. Flay was previously married three times to 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. He was also romantically linked to Heléne Yorke from 2016 to 2019.
During Tuesday’s podcast, Flay and Cavallari discussed dating at length since the chef is back on the dating scene. (Cavallari is also single, having split from boyfriend Mark Estes last month.)
“I’ve been on television basically my entire adult life. So, I like keeping as much as I can in my private life to myself,” Flay admitted. “That said, it seems like there are some people who are interested in what I’m doing in my personal life. I’m not really sure why. It’s not that exciting.”
