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Kristin Cavallari finally owns up to Craig Conover fling, suggests there was an ‘overlap’ with Paige DeSorbo

June 5, 2025
in News
Kristin Cavallari finally owns up to Craig Conover fling, suggests there was an ‘overlap’ with Paige DeSorbo
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Kristin Cavallari finally pulled back the curtain on her long-rumored romance with Craig Conover.

The “Honestly Cavallari: The Headline Tour” star owned up to the fling during Wednesday’s “Watch What Happens Live With Andy Cohen.” She even dished on the timeline, implying that the reality TV star dated her and Paige DeSorbo at the same time.

Host Andy Cohen bluntly asked Cavallari, 38, whether there was “overlap.”

Kristin Cavallari
Kristin Cavallari implied she and Paige DeSorbo briefly dated Craig Conover at the same time. Stephanie Diani/E! Entertainment via Getty Images
“Watch What Happens Live” host Andy Cohen asked her Wednesday about “overlap” in the romances. Watch What Happens Live with Andy Cohen/Youtube
Craig Conover in NYC
The “Hills” alum said she and Conover’s friendship only “became romantic for two seconds.” Christopher Peterson / SplashNews.com

The “Hills” alum clarified that she “politely excused” herself from Conover’s life when she “caught wind” the Bravolebrities were seeing each other.

“There was a picture of Craig and Paige in New York — I’ll never forget it — and it looked like they were sort of together,” Cavallari recalled. “That was the first time anyone had seen them. That was the first time I had heard about it.

“I saw that picture, and I texted him and I said, ‘Hey, let’s just be friends,’” she continued.

She subsequently saw a photo of the “Southern Charm” star and DeSorbo looking “sort of together.” paige_desorbo/Instagram
Cavallari then asked Conover via text to be “just … friends.” Farreno Ferguson/Bravo

Cavallari noted that, prior to this, she and the “Southern Charm” alum, 36, had been “friends” who “became romantic for two seconds.”

Conover and Cavallari’s friendship began in 2020 following her divorce from Jay Cutler.

The “Laguna Beach” alum also became close with Austen Kroll at the time — and denied dating the fellow reality stars the following year.

Craig Conover and Paige DeSorbo
Conover went on to date DeSorbo from 2021 to 2024. PGA TOUR
Kristin Cavallari via Instagram
Cavallari made more dating confessions on “WWHL.” Instagram/@krisitncavallari

“These two guys who I have been linked to for the past year are my friends,” she wrote via Instagram in 2021. “That’s it. It’s possible for a grown woman to be friends with a grown man.”

In 2023, however, she admitted on “WWHL” that she “may have been drunk one night and kissed Craig.”

By that time, Conover was with DeSorbo, 32.

Glen Powell in NYC in April 2025
Cohen asked her about “dry hump[ing]” Glen Powell on a Greece vacation. GC Images
Kristin Cavallari via Instagram in April 2025
Cavallari confirmed they left their pants on for the hookup. Kristin Cavallari/Instagram

The couple dated for three years before calling it quits in November 2024.

Cavallari, for her part, had a months-long relationship with Mark Estes in 2024 and has since made headlines for hookups with country singer Morgan Wallen, NHL player Nate Thompson and more.

She also revealed a “dry hump[ing]” session with “Top Gun” star Glen Powell in Greece during her show’s premiere Wednesday — but insisted to Cohen, 57, that they kept their pants on.

The post Kristin Cavallari finally owns up to Craig Conover fling, suggests there was an ‘overlap’ with Paige DeSorbo appeared first on Page Six.

Tags: Bravocraig conoverkristin cavallariPaige DeSorboreality starsSouthern CharmSummer Housethe hillsWatch What Happens Live
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