Craig Conover and Kristin Cavallari Clear Up Their Relationship Timeline

Craig Conover and Kristin Cavallari are setting the record straight on their years-long connection, following a recent reunion that reignited fan curiosity. The “Southern Charm” star and the Uncommon James founder recently joined forces with Austen Kroll for the Boston leg of Cavallari’s “Let’s Be Honest” podcast tour, prompting fresh looks at their past.

From DMs in 2020 to “Summer House” rumors in 2021, here’s how the duo is clarifying their timeline amid speculation of romance and friendship.

Kristin Cavallari and Craig Conover’s Podcast Reunion Sparks Timeline Recap

Conover and Cavallari have finally put the romance rumors to rest, cementing their status as friends after a headline-filled journey.

The latest chapter unfolded when Cavallari hosted Conover and Kroll onstage during her podcast tour’s second night in Boston, a moment she dubbed “lots of laughs” on her Instagram Story. The trio posed for photos alongside Cavallari’s longtime friend Justin Anderson, with Kroll reposting fan snaps to his own account.

According to Kroll, this public reunion comes after their friendship began five years ago when Cavallari messaged Conover ahead of a Nashville visit.

“Honestly, she slid into Craig’s DMs and was like, ‘I’m coming into town,’ so we all went to dinner,” Kroll revealed on “Watch What Happens Live” in December of 2020.

The group clicked instantly, sparking a bond that’s lasted through years of rumors. Cavallari dismissed romance talk from the beginning when she wrote on Instagram, “I didn’t realize I wasn’t allowed to have FRIENDS that are guys.”

From Rumored “Summer House” Fling to Friendship Confirmation

Speculation peaked in 2021 when “Summer House” season 6 (filmed that year, aired 2022) saw Lindsay Hubbard question Conover about a rumored fling with Cavallari. Conover admitted to girlfriend Paige DeSorbo he’d “hooked up with her before,” while Kroll later claimed jealousy over Conover “making out” with her.

Cavallari refuted the chatter on Instagram, insisting, “I’ve never dated either one of them,” and vowing no future romance. She clarified further on WWHL in September 2023, admitting, “I may have been drunk one night and kissed Craig,” but denying anything with Kroll.

She attributed past hype to a “drunk night” of dancing that “got blown out of proportion.” Fast-forward to 2025, and Cavallari told Andy Cohen on WWHL she remains “still friends with them,” with plans to dine with Kroll in Nashville soon. Conover, now split from DeSorbo, and Kroll have kept the friendship alive, as evidenced by their latest podcast cameo.

Fans can catch Conover and Kroll on “Southern Charm” season 10, airing Thursdays on Bravo and streaming next day on Peacock, while Cavallari’s tour docuseries hits E! on June 5.