Did Craig Conover hook up with Kristin Cavallari while starting another relationship with Paige DeSorbo? The world may never know, but Kristin did try to glean the truth from Craig recently on her new series, Honestly Cavallari: The Headline Tour.
For a while, Kristin denied all rumors involving Craig. However, several weeks ago, she appeared on Watch What Happens Live. Here, Kristin admitted that they did hook up, and there likely was an overlap event involving her and Paige.
Kristin also noted that she had already grilled Craig about her suspicions in her new series. She wants viewers to watch her headline tour, so she gave no further details on WWHL. But now that this episode featuring Craig has aired, we have several additional notes to add to this storyline. And these details made Craig madder than the honeybee he rode in on, as overheard in a hot mic moment after he walked off her stage.
Kristin Cavallari Wants To Have Paige DeSorbo On Her Podcast After Craig Conover Breakup
Kristin Cavallari and Craig Conover’s history explained
Before discussing what happened on her headline tour, allow us to Juvenile ourselves by backing our asses up and explaining how we got here in the first place. In 2020, Kristin, Craig, and his Southern Charm castmate, Austen Kroll, started hanging out. Shortly after, Paige and Craig also got close.
Around this time, images of the friendship between Kristin, Craig, and Austen went viral. After, speculations about a potential hookup involving Kristin and one of these men emerged. Kristin denied this claim, but most viewers remained unsure, speculating for two additional years that maybe she and Austen were the subjects matching these assertions.
In 2022, Craig visited Paige on her series, Summer House. As Season 6 aired, we all walked through the early stages of their relationship. Then, Lindsay Hubbard dropped a bomb that shocked everyone. She revealed that this claim was legit but that it was Craig, not Austen, who had been hooking up with Kristin in 2020.
Paige was annoyed. As was Kristin, who did not love hearing her name spoken poorly about in this series. Taking control of the situation, Paige explained that Craig was bothered by Kristin, as Kristin denied these claims online. Paige also recalled that Craig admitted that he and Kristin had “f*cked,” but as Craig stressed, he did not cheat on Paige with Kristin.
Craig Conover suffered a hot mic moment after his chat with Kristin Cavallari
Now that the truth is out there and everyone has finally admitted that this hookup narrative is real, one detail remains. Did Craig hook up with Kristin while starting something else with Paige? Was there any overlap between these two women? As Kristin confessed recently on WWHL, she suspects that an overlap was indeed at play.
Taking matters into her own hands, Kristin invited Craig and Austen to film for her headline tour, Honestly Cavallari. Before their appearances, Kristin admitted that she was not “expecting Craig” to come clean on her stage by admitting that he had lied to her and Paige about this overlap chronology. Regardless, Kristin planned on giving Craig “a hard time about it” anyway.
Once these boys took the stage, Kristin asked Austen, “Did anything ever happen between the two of us?” Austen replied, “You and me? No.” Turning to Craig, Kristin quipped, “Craig, we started hanging out, and Austen was taking the heat for it.”
“No one ever really knew what was going on. We had all met at that time and just hit it off, and we all had a blast,” Craig responded. As Kristin continued her line of questioning, Craig (somewhat) revealed the truth, clarifying that there was an overlap, but not as much as everyone thought. According to Craig, once he and Paige turned monogamous, he and Kristin “stopped talking.”
Following their interview, Craig walked off stage, telling Austen, “This is about the dumbest thing I’ve ever done in my life. The whole f*cking thing was Paige. F*ck that.”
Cue Austen, reminding his buddy that he was still wearing a mic.
Craig Conover and girlfriend Natalie Buffett update (June 2025)
Before walking off the stage and getting caught with his mic around his chest, Kristin, Craig, and Austen played a game of truth or dare. Following a dare that asked Kristin to kiss Craig, Craig rejected Kristin, citing, “My Raya date is more than just a Raya date. So, I can’t.”
Following the show, Kristin joined Craig and Austen backstage. Here, Craig told her that had he not been “dating someone, I would have kissed you on stage. But I was like, ‘No one knows I’m dating someone,’” seemingly suggesting that Kristin had forced him to expose his relationship status to the masses.
Filming for the Honestly Cavallari tour took place a while ago. This Raya girlfriend that we just heard about last night on E! is already a thing of the past. However, we do now know that her name is Natalie Buffett.
Sadly, Craig and Natalie are already dunzo, a word that Kristin herself coined eons ago, following her car breaking down in 2004 on Laguna Beach. As Craig recently noted, he was not ready to date anyone new. But he did not realize this at the time they started dating.
Maybe he should call Kristin? Too soon?
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