Bobby Flay and Kristin Cavallari Recall Their Awkward Encounter in the DMs

Celebrity chef Bobby Flay, 59, and reality star Kristin Cavallari, 37, recently shared an amusing misunderstanding from their social media history during the latest episode of Cavallari’s Let’s Be Honest podcast. The conversation revealed how a simple dinner invitation led to an unexpected rejection.

“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 recounted. “I said, ‘I’m going to be in Nashville for one night. Can I take you to dinner?’”

Cavallari immediately interpreted the message as a romantic overture, responding with refusal. “I was like, ‘I’m over dating right now.’ I was burnt out on dating or something,” she explained. Flay remembered her saying she was “already” seeing someone, to which he clarified, “I just want to go to dinner with you.”

The Laguna Beach alum acknowledged her hasty assumption: “I think the ‘take you to dinner’ thing is more where it was like, ‘Oh, that seems like a date.’” She suggested alternative phrasing: “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.’” Flay accepted the feedback gracefully, saying, “my bad” for the miscommunication. “Listen, it worked out. It’s all good,” Cavallari added. “We ended up going to dinner. It was fine.”

During the podcast, they also discussed modern dating challenges, with Flay sharing insights about his approach to romance in the digital age. “My ex-girlfriend, who is the loveliest person in the world, we were put together by a mutual friend,” he explained. “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.’” Cavallari praised this as a “great move,” noting it’s a “great way to gauge” a possible connection.

Currently, both celebrities find themselves single. Cavallari recently ended her relationship with TikTok star and Montana Boyz member Mark Estes in September due to concerns with their 13-year age gap, while Flay and Pérez concluded their three-year relationship in June. The chef has been married three times: to Debra Ponzek from 1991 to 1993, Kate Connelly from 1995 to 1998 — and with whom he shares daughter Sophie Flay — and actress Stephanie March from 2005 to 2015. He was also romantically linked to Heléne Yorke from 2016 to 2019.

When questioned about future marriage prospects, Flay hesitantly 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 remains open to partnership, adding, “I would be interested in a life partner. But I don’t think it necessarily needs the documentation.”