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

While diehard Laguna Beach fans will forever ship Kristin Cavallari and her high school boyfriend, Stephen Colletti, the longtime TV personality has had a handful of significant partners since the early 2000s. In fact, Kristin’s longest relationship was with estranged husband Jay Cutler. Unfortunately, the Hills alum announced the pair’s split in April 2020.

“With great sadness, after 10 years together, we have come to a loving conclusion to get a divorce,” Kristin, who shares children Camden, Jaxon and Saylor with the retired NFL player, wrote on Instagram at the time. “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. This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family.”

Since going public with their breakup, Kristin has opened up on a number of occasions about how she’s coping. “I actually sort of look at it as though it was a good thing to go through this in the middle of quarantine because it really forced us to hibernate. You know, we couldn’t leave our houses,” the former E! personality told Morgan Stewart during a September 2021 episode of Daily Pop. “So, in that sense, it was actually nice because it was a lot of time where I was able to reflect and focus on myself and not have to do interviews or see people. I was actually really thankful that we went through it at the time that we did.”

“It was not a decision that I made overnight, obviously,” the Uncommon James founder said in a July 2022 episode of the “She Pivots” podcast. “I really sat on it for a long time,” she added, noting that she is “sick” of talking about her divorce.

“It was the scariest decision I’ve ever made, but it’s been the best decision I’ve ever made for myself,” Kristin said. “And that’s not to say that it hasn’t been really hard the last few years.”

As for the former reality star’s love life, the Colorado native is back in the dating pool. While she and Stephen briefly sparked romance rumors after reuniting in early August 2021, their relationship appears to be strictly platonic as the friendly exes even launched a podcast titled “Back to the Beach” in July 2022.

Since her divorce, Kristin admits that she’s “been on quite a few dates,” adding that she has been using Instagram DMs as a dating app.

“I can’t filter through all of my DMs, but I can see those blue checkmarks, honey!” she said during a July 2022 appearance on the “Not Skinny But Not Fat” podcast. “Sorry, I’m only gonna go for the verified!”

Keep scrolling to learn more about Kristin Cavallari’s complete dating history over the years!

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.

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.

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.

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.