Joshua Goldman
Joshua Goldman
min read · June 6, 2025 · Entertainment

Cavallari's Candid Confessions: Love, Hookups, and Hollywood Secrets!

Kristin seen here September 10, 2023

KRISTIN CAVALLARI EXPOSES HER DIRTY LITTLE SECRETS!

The lovely Kristin Cavallari, 38, has been making waves in the reality TV world with her new show "Honestly Cavallari: The Tour." But what fans really want to know is about her romantic exploits. And boy, does she deliver!

In a juicy conversation on Andy Cohen's Watch What Happens Live, Kristin spills the beans about her brief but torrid romance with Southern Charm's Craig Conover. When asked about the relationship, Kristin coyly replied, "We were friends first [and] became romantic for two seconds." But that was just the beginning of the drama.

But now, she's coming clean about a fling she had with Southern Charm's Craig Conover. Craig seen here with ex-girlfriend Page DeSorbo on October 14, 2022

It seems that Kristin had no idea that Craig was already dating Paige DeSorbo, 32. "The second I caught wind of Paige, I very politely excused myself from the situation," she confessed to Andy Cohen. Ouch! Looks like someone got burned!

But it gets even juicier! When asked if there was any overlap in their relationships, Kristin revealed that Craig had posted a picture with Paige in New York, which made her realize he was already taken. "I saw that picture, and I texted him and said, 'Hey, let's just be friends.' Like, I don't wanna get in the middle of this," she explained.

The whole ordeal happened in 2023, but it's clear that Kristin still has feelings for Craig. When a fan asked about her relationship with Southern Charm's Austen Kroll and Conover, Kristin laughed and said, "We were all really good friends for a while... and we had a drunk night and we all posted some stupid Instagram dancing around." But when pressed by Andy Cohen about whether she'd ever kissed Craig, Kristin sheepishly admitted, "I may have been drunk one night and kissed Craig."

The Honestly Cavallari: The Tour star, 38, opened up about the romance to Andy Cohen , 57 on Wednesday's Watch What Happens Live

But that's not all! In the premiere episode of her new show, Kristin also confessed to a steamy encounter with Hollywood heartthrob Glen Powell. "Justin, my best friend, spilled the tea on our date," she said, laughing. "We were partying in Greece when Glen literally ran into me." Ooh la la!

And what happened next? Well, let's just say that Kristin and Glen got a little too close for comfort. When Justin asked if they had "dry humped," Kristin playfully smiled and said, "Yeah, we did."

When the news of her date with Glen came out, Kristin took to social media to defend herself, saying, "I have to go on record, when this comes out, I had nothing to f*ing do with it!" But fans know better - after all, there's no such thing as a secret in the reality TV world!

Kristin this week admitted to going on a date and 'dry humping' Hollywood superstar Glen Powell (pictured)

In conclusion, it seems that Kristin Cavallari is living her best life, hooking up with Hollywood heartthrobs and Southern Charm studs alike. Who knows what's next for this beautiful blonde? One thing's for sure: we can't wait to see what drama she brings on her new show!