Details About The Relationship Between Kristin Cavallari And Craig Conover

Most of us know Craig Conover from Bravo's "Southern Charm," or from when he joined the casts of the network's series, "Summer House" and "Winter House." Bravo fans know plenty about Conover's relationship with "Summer House" sweetheart, Paige Desorbo. What some might not know much about, however, is Conover's past relationships. Desorbo isn't the star's first time romancing a reality TV star. Rumors have swirled that he got cozy in the past with none other than "Laguna Beach" leading lady, Kristin Cavallari. As it turns out, this unlikely reality TV pair did have a fling, but what exactly happened is a case of he said, she said.

It seems reality stars always run in the same circles even if they're not on the same series. Consequently, Cavallari struck up a friendship with "Southern Charm" stars, Conover and Austen Kroll. In 2020, Kroll told Us Weekly just how the friendship began. "She came to town with her friend Justin and the four of us [with Craig] had dinner. We've all been in contact ever since. We're in this, like, big old group chat, and the group chat is active." The rest was history, and the friend group made in reality TV heaven remained long after the first meeting. Still, that doesn't mean that everything that went on in this trio was platonic. It seems that one of the "Southern Charm" boys managed to charm Cavallari but what went down has never been entirely confirmed.

Leave it to "Watch What Happens Live" host, Andy Cohen, to get to the bottom of Bravo romance rumors. He asked Kristin Cavallari about the rumors when she appeared on the show in September 2023. He asked about Austen Kroll, saying, "What is it there? Did you guys date? Hook up? Friends? Friends with benefits?" Cavallari referenced a 2020 Instagram post featuring the pals partying that, in her words, "got all blown out of proportion," per People. She confirmed that nothing romantic occurred between her and Kroll.

As for Craig, though, "I may have been drunk one night and kissed Craig," Cavallari admitted. While this may have been the first time she fessed up to her fling with Conover, it's not the first time she addressed the rumors. In 2021, she took to her Instagram story to set things straight. "My one and only love triangle was documented in high school," the star said, via People, referring to the famous drama on "Laguna Beach" with her fellow stars, Stephen Colletti and Lauren Conrad. Her relationship with Conover and Kroll, she assures the world, is nothing like that. "I've never dated either one of them. I can guarantee that I'm not going to date either one of them. It's possible for a grown woman to be friends with a grown man, and for that to be it," she explained. Still, despite her words, Conover's take was a bit different.

In October 2021, Craig Conover made things official with "Summer House" costar, Paige DeSorbo. Just a few months later, an episode of "Summer House" premiered in which Conover told DeSorbo, "I've hooked up with her before" about Kristin Cavallari (via Us Weekly). This episode was filmed in July 2021. Conover also implied that despite her claims otherwise, Cavallari had had some kind of romance with Austen Kroll, adding that his friend "hates that I was making out [with Kristin.]"

At the time, Cavallari denied any kind of romance with Conover. Yet, in a later episode from that season, DeSorbo discussed text messages between her soon-to-be boyfriend and Cavallari. "I guess she texted him like, 'You are not going to make me look like an idiot with her.' And like, 'If you want her, like, go have her. Just don't make me look stupid,'" DeSorbo said. As for Conover's response, she said, "he was like, 'OK, but you went on Instagram and lied.' Like, 'You can't say you were never going to date either of us. We f***ed.'"

So, while Cavallari eventually admitted to a drunken makeout with Conover, they were never in complete agreement about how far things went. Yet, it seems that now, it's all water under the bridge. On "Watch What Happens Live" in September 2023, Cavallari said that the trio is "still friends," per People.