Christine Cavallari Discusses Romance with Craig Conover

Christine Cavallari has opened up about her past relationship with Craig Conover.

During an episode of “Watch What Happens Live with Andy Cohen,” she shared some interesting insights about the timeline of their connection. Cavallari also hinted that she had been dating Conover while seeing Page DeSorbo as well.

Cohen, the host, directly asked Cavallari about her romantic situations. “Was there any overlap?” he inquired, noting her age of 38.

Cavallari revealed that she became aware of some mutual pictures of Conover and DeSorbo in New York, which, she recalls, was surprising for her. “I’ll never forget that moment; it was the first I heard about them together,” she said.

Upon seeing those images, she texted Conover to suggest they should “just be friends.”

Reflecting on their friendship, Cavallari mentioned that the two had a brief romantic period but considered it more of a fleeting moment than anything serious. “It became romantic for just a couple of seconds,” she noted.

Post-divorce from Jay Cutler in 2020, Cavallari and Conover formed their friendship. Interestingly, she also addressed rumors about her dating life, stating in 2021, “These two guys I’ve been linked to are just my friends. A grown woman can be friends with a grown man.”

However, she later acknowledged in a 2023 segment that there might have been a night when things escalated between her and Conover: “I might have been drunk one night and kissed Craig.”

By then, Conover was in a serious relationship with DeSorbo, who is now 32. They had dated from 2021 until late 2024, a three-year stretch before parting ways.

Cavallari, for her part, had a brief romance with Mark Estes the following year. She also captured media attention for rumored links with country singer Morgan Wallen and NHL player Nate Thompson.

In a lighter moment, she humorously shared that she had a playful encounter with actor Glen Powell while on vacation in Greece, confirming that they kept things relatively PG, saying they “left their pants on.”