Looking Back at Kristin Cavallari's Star-Studded Dating History

Before her 10-year relationship with Jay Cutler, Kristin Cavallari had a star-studded dating history that included Chris Evans, Stephen Colletti and more

By Tierney Bricker Apr 27, 2020 6:30 PMTags
Watch: Kristin Cavallari & Jay Cutler Divorcing After 10 Years Together

Kristin Cavallari and Jay Cutler are dunzo. 

"With great sadness, after 10 years together we have come to a loving conclusion to get a divorce," Kristin announced on Instagram on Sunday. "We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of."

Kristin and Jay share three kids together—Camden Jack Cutler, Jaxon Wyatt Cutler and Saylor James Cutler—with a source telling E! News, "They have tried to work it out for years. The kids definitely kept them together at times."

The couple first started dating in 2010, which came after several high-profile romances for Kristin, whose love life has garnered attention ever since she starred on Laguna Beach as a high school junior.

And Jay actually isn't the first NFL quarterback Kristin, 33, dated, with the Very Cavallari star briefly dating a Heisman Trophy winner during her time on the MTV reality hit. (Sorry, Stephen!)

Kristin Cavallari and Jay Cutler: Romance Rewind

So which A-listers did Kristin spark romance rumors with post-Laguna Beach? And who was she secretly dating during her time on The Hills? Find out by looking back on Kristin's star-studded dating history...

Stephen Colletti

You never forget your first love...especially when MTV's cameras are around to document every high and low in the dramatic relationship. Viewers got to see Kristin and Stephen's love story play out on Laguna Beach for two seasons, with the pair, who began dating the year before the show began filming, and Lauren Conrad delivering one of TV's great love triangles.

"We loved hard and fought hard. My relationship with Stephen went from our own high school romance to the fodder of a hugely successful television show," Kristin wrote in her 2016 book, Balancing in Heels. "Stephen was the most important thing in my life, and there was nothing I cared about more. I hated fighting with him on camera because it felt like I was airing all our dirty laundry."

While their romance couldn't make it out of high school intact, the two have remained friends, with Kristin once telling E! News he was down to make an appearance on Very Cavallari.

Matt Leinart

In the season two premiere of Laguna Beach, Stephen is devastated when he learns Kristin has moved on after he left for school, dating "Matt, this guy at USC."

This guy at USC would turn out to be Matt Leinart, USC's star quarterback who would go on to play in the NFL. Matt never ended up appearing on the MTV hit and his romance with Kristin was short-lived.

The pair briefly sparked reconciliation rumors when they were spotted together in Vegas in 2008, but Kristin and Matt never got back together.

Brody Jenner


While they would later fake a romance for The Hills' later seasons, Kristin and Brody did date years prior shortly after her tenure on Laguna Beach ended when they were introduced by her co-star Talan Torriero

"I dated Brody when I was 18, right after Laguna Beach, actually, and that's it," she spilled on Bethenny in 2012. " And then on the show, on The Hills, they had us 'dating' for a few episodes."

The pair dated on and off for almost a year before calling it quits in 2006. "It's just hard right now because I am working all the time," she told People at the time. "We're still good friends though."

Nick Lachey

Kristin and the 98 Degrees singer sparked romance rumors when they were spotted together in early 2006, a year after his high-profile split with Jessica Simpson.

But Kristin shot down the rumors, telling People, "There's nothing to talk about, there's nothing going on. He's a nice guy, but I'd have to say we're just friends."

Years later, when Nick interviewed Kristin for VH1's Big Morning Buzz, they joked about their sons sharing the same name, Camden.

Nick Zano

Shortly after her romance with Brody fizzled out, Kristin began dating actor Nick Zano, best known for the WB sitcom What I Like About You.

Things were pretty serious between the two, with Kristin even getting his initials tattooed on her wrist. 

But when the pair called it quits in December 2007 and they were officially dunzo, Kristin had the tattoo removed.

Chris Evans

Back in 2008, Kristin was reportedly dating the future Captain America after The New York Post claimed they were spotted "hooked up" at the opening of Cabana One at the Mayfair Hotel in Miami.

Once again, Kristin had to shoot down rumors about her own dating life, telling Us Weekly, "I hear that too! No, we're just friends. I've known Chris for awhile, just through mutual friends. I've known him for a few years, actually."

Miguel Medina

While Kristin was faking romances on-screen with Brody Jenner and Justin Bobby, she was actually secretly dating someone behind-the-scenes during her time on The Hills.

In 2010, Kristin was dating MTV camerman Miguel Medina, managing to keep their relationship a secret even from her co-stars Heidi Montag and Audrina Patridge.

"We dated for a few months and nobody knew," she revealed to her former co-stars in a recent episode of Very Cavallari. "And I was dating Brody on the show and like, meanwhile, Miguel was, like, filming it."

She then went on to say their relationship was exposed toward the end of their time working together because "paparazzi got us at the airport a week before we wrapped the show. That's how we got caught."

After their romance ended, Kristin began dating Jay. 

Catch up on Very Cavallari right now.