Kristin Cavallari's Dating History: Ex-Boyfriends and More

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Stephen Colletti

Kristin and Stephen dated on-and-off from 2001 to 2005.

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Talan Torriero

As Laguna Beach fans might remember, Kristin, Talan and Stephen had a bit of a love triangle going on. She would often date Talan during the periods she and Stephen were on the outs.

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Matt Leinart

During season 2 of Laguna Beach, Kristin revealed she moved on from Stephen with a guy named Matt who played football at the University of Southern California. Matt was the quarterback for USC at the time and later went on to play in the NFL. He and Kristin only dated for a few months and he never appeared on the show.

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Brody Jenner

Kristin and Brody dated for nearly a year from 2005 to 2006.

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Nick Lachey

After Nick and Jessica Simpson called it quits in 2006, he and Kristin had a brief fling.

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Nick Zano

Kristin and the actor dated from 2006 to 2007 before calling it quits. According to multiple outlets, Kristin got Nick’s initials tattooed on her wrist while they were together.

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Jay Cutler

Kristin and Jay dated for eight months before getting engaged. Then, in July 2011, the couple split up for three weeks — and Kristin even gave Jay her engagement ring back!

“A few things needed to change, and I knew the only way Jay would see how serious I was, was if I ended the relationship,” she wrote in her 2016 novel, Balancing in Heels: My Journey to Health, Happiness, and Making it all Work. Kristin and Jay eventually tied the knot in 2013 but called it quits in April 2020.

The former flames celebrated their 10-year relationship with a cryptic post that sparked reconciliation rumors in January 2021. “The world is full of users. 10 years. Can’t break that,” the pair captioned their posts. However, neither Jay nor Kristin addressed the speculation.

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Jeff Dye

According to In Touch, Kristin and Jeff “started off as friends” before their relationship “turned into something more.”

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Chase Rice

Kristin was linked to country music star Chase Rice in August 2021 with a source telling Us Weekly the two had been spotted “on a couple of dates.”

Just two months later, however, she took to Instagram to set the record straight. “I’ve just been having fun. I haven’t wanted a boyfriend. But I’m currently not dating anyone,” she said via her Instagram Stories.

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Tyler Cameron

Romance rumors between Kristin and Tyler first stared swirling in April 2022 when they were spotted smooching on camera for what turned out to be an Uncommon James video shoot.

“Tyler is the sweetest human being on the planet, such a great guy, I was so impressed with him,” Kristin told Entertainment Tonight at the time. “I hired him to play my love interest in a campaign video. There is nothing going on. Great guy, [but] we are not dating, I promise.”

Months later, they sparked dating speculation once again when spending New Year’s Eve together.

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Mark Estes

Kristin and Mark – known as one of the Montana Boyz on TikTok – went public with their relationship with a selfie from a romantic Mexican getaway. The handsome couple share a 13-year age gap, which fans were quick to point out in the comments section of her post.