Relationship History
Kristin Cavallari’s Relationship History: Jay Cutler, Stephen Colletti & More
Kristin Cavallari’s getting candid on her new E! show, Honestly Cavallari: The Headline Tour.
The longtime reality star filmed her podcast tour and began rolling out episodes on June 4. We’ll see the Laguna Beach alum chat with celeb pals and notable figures in her life — which includes some exes.
After Laguna Beach aired in the early 2000s, Cavallari didn’t take a break from the spotlight, subsequently appearing in The Hills and Very Cavallari. Consequently, the 38-year-old’s love life has made the news for years, from her marriage to former NFL player Jay Cutler, to a rumored love triangle with Southern Charm’s Craig Conover and Austen Kroll.
While Cavallari will touch on the latter topic in her new show — the duo will turn up later in the season — she’s already dishing about past romances and flings two episodes in. In fact, she just revealed that she had a “fun night” with actor Glen Powell during a recent trip to Greece.
If that piqued your curiosity about Cavallari’s past relationships, you’ve come to the right place. Keep reading for a deep dive into the stars she’s been linked to before, from her MTV days onward.
Stephen Colletti
Stephen Colletti, who starred on One Tree Hill, and Cavallari’s on-again-off-again love story began before Laguna Beach, and it was captured on camera for two seasons before they ultimately broke up when Colletti graduated from high school. The pair are still friends, according to a 2018 Us Weekly interview.
Talan Torriero
During Laguna Beach filming, Cavallari and Torriero also had a brief high school romance, though it wasn’t a full-fledged relationship. In a podcast episode with former costar Lauren Conrad, Cavallari dished, “We all were [hooking up with Torriero].” Torriero later responded by lip-syncing to Taylor Swift’s “Anti-Hero” on TikTok.
Matt Leinart
At 18, Cavallari dated Matt Leinart, a then-USC quarterback, during Season 2 of Laguna Beach. It lasted six months, though in 2023, Cavallari said on the “Back to the Beach” podcast that she’s “actually still good friends with Matt.”
Brody Jenner
Another celeb Cavallari was linked to is Brody Jenner. It was genuine when they briefly dated pre-The Hills, but when their relationship made its way to the screen, Cavallari admitted that it was for show. “They pretended that him and Jayde [Nicole] broke up and I was dating Brody, and Jayde and I got into a huge fight because she saw us in a club,” she told E! News. “It wasn’t real at all. They were together the entire time.”
In fact, Cavallari has said that she was really in a relationship with MTV cameraman Miguel Medina at the same time. “We dated for a few months and nobody knew,” she said during an episode of Very Cavallari. “And I was dating Brody on the show and like, meanwhile, Miguel was, like, filming it.”
Nick Zano
What I Like About You actor Nick Zano was linked to Cavallari, who ended up getting his initials tattooed on her wrist. According to E! News, she had it removed once the relationship fizzled out in 2007.
Jay Cutler
In 2010, the reality star entered a relationship with Jay Cutler, a former Chicago Bears quarterback. They got engaged one year later, and after a brief breakup, they got back together, had their first child, and proceeded to tie the knot in 2013. Nearly a decade and two more kids later, the couple separated in 2020.
Jeff Dye
After five months of dating, the reality star and comedian Jeff Dye called it quits in 2021. “We didn’t even really date,” the comic said. “I’m gonna say that publicly. She made me think that I might have a chance with her. She treated me like a little puppy.”
A couple of years later, Cavallari mentioned on her “Let’s Be Honest” podcast that an ex was arrested for a DUI in front of her. Though she didn’t refer to him by name, Dye expressed his outrage at Cavallari sharing the story, saying, “It was very terrible, and it hurt my feelings a lot.”
Craig Conover
It’s not clear when exactly Cavallari dated the Southern Charm star, but she recently confessed on Watch What Happens Live to have dated Conover at some point when he was allegedly seeing Summer House‘s Paige DeSorbo. That relationship was confirmed in October 2021, but they have since broken up.
“So, Craig and I were friends first [and] became romantic for two seconds,” Cavallari said. “The second I caught wind of Paige, I very politely excused myself from the situation.”
Mark Estes
After being spotted with country singer Chase Rice — who Cavallari hasn’t confirmed she was ever in a relationship with — the Laguna Beach alum began dating Montana Boyz TikToker Mark Estes. It lasted for a few months in 2024; according to People, their 13-year age gap played a part in their breakup, but there were no hard feelings.
Morgan Wallen
Cavallari divulged on the “Dumb Blonde” podcast that she and country singer Morgan Wallen were briefly romantic, noting that “he was a true gentleman” on their first date. (The pair were first rumored to have been seeing each other back in September 2023). She then went on to add that the relationship, however, was “a lot,” and she was the one to end it.
Nate Thompson
Calling it “one of the deeper relationships [she’s] had,” Cavallari’s short romance with former NHL player Nate Thompson ended in March. On her podcast, the reality star clarified that things ended because she “just didn’t wanna be in a relationship” at the time.
Thompson also had positive feelings toward Cavallari post-breakup, saying on a podcast that “she’s a really, really good person and great mom and yeah, it was fun.”
