Kristin Cavallari Dating History: Pro Athletes, Reality Stars and More (2025)

From reality stars to NFL athletes, Kristin Cavallari has had her fair share of high-profile romances over the years.Cavallari rose to fame on MTV’s Laguna Beach in 2004, at which time she was dating high school sweetheart Stephen Colletti. The pair’s real-life romance and alleged love triangle with Lauren Conrad was central to the show’s story line.After her split from Colletti, Cavallari romanced another classmate, Talan Torriero. However, it was her relationship with Jay Cutler, which began in 2010, that led to marriage.The twosome welcomed sons Camden and Jaxon and daughter Saylor during their nearly seven-year marriage. However, they called it quits in 2020.Cavallari’s love life has continued to make headlines in the years that have followed. “I’ve gone through phases of going on a million first dates, and I’ve gone through phases where I’m not dating at all,” she exclusively told Us Weekly in September 2023. “At the moment, it’s not my priority, but I’m open to it.”Scroll down to look back at Cavallari’s star-studded dating history:

Remember when? Cavallari and Colletti took their romance from the halls of their high school to reality TV in 2004. Though their relationship didn't last long, the Balancing in Heels author remembered that they "loved hard and fought hard."

The Laguna Beach costars hooked up in the early days of the reality series.

Following her flings with her MTV castmates, Cavallari moved on with Leinart, then a star quarterback at USC. He later went on play professionally for the Arizona Cardinals in 2006, Houston Texans in 2010, Oakland Raiders in 2012, and Buffalo Bills in 2013.

Before their onscreen relationship in The Hills, the reality stars dated when Cavallari was 18 years old. Their romance fizzled out after nearly a year of dating.

The former 98 Degrees singer and the California native briefly dated in 2006 after Lachey's big split from Jessica Simpson. Nearly 10 years later, the former couple joked about how their sons share the same name during an interview on VH1's Big Morning Buzz.

Cavallari was so serious about the What I Like About You alum that she reportedly got his initials tattooed on her wrist after they started dating in 2006. One year later, however, they pulled the plug on their romance.

After the New York Post reported in 2008 that Cavallari and the Captain America star had hooked up in Miami, the jewelry designer reassured Us that they were just friends. "I've known Chris for a while, just through mutual friends," she said at the time.

Cavallari continued to shut down the years-long dating rumors during an April 2025 episode of her “Let’s Be Real” podcast, telling fans, “Chris Evans and I had a similar friend group, and I think that we were at an event one night as a group, like, there was a group of us there. We saw each other socially. I never dated Chris Evans, ever, ever, ever. Didn't even go on one date with him. Literally, nothing ever happened. And there's been these rumors for years that we dated. Well, we never dated.”

After Laguna Beach went off the air, Cavallari returned to reality TV as part of The Hills in 2009 and quickly landed in a love triangle with Brescia and Audrina Patridge. When the series celebrated its 10th anniversary, however, Patridge claimed the relationships were fabricated.

Cavallari clarified that she and Brescia never dated during an April 2025 episode of her “Let’s Be Real” podcast. “Not one time did I see him outside of filming. I think the only time I kissed him was when they asked me to kiss him on camera,” she stated. “And listen, back in the day, I was like, ‘Yes, I'm a team player.’ I was getting paid for The Hills like I would a scripted show. … [I] never saw him outside of filming. I never dated him.”

Cavallari later opened up about "fake dating" during her reality TV days and blew her costars minds when she revealed that she was secretly dating the MTV cameraman in 2010. "We dated for a few months and nobody knew," she told Patridge and Heidi Montag when they reunited on Very Cavallari. "I was dating Brody on the show and like, meanwhile, Miguel was filming it."

After her relationship with Medina lost its spark, Cavallari fell in love with the former Chicago Bears quarterback in 2010. They tied the knot in Nashville three years later, but confirmed "with great sadness" that they were calling it quits in April 2020. A source later told Us that the pair would often "accuse each other of cheating" during their "antagonistic" relationship.

The comedian was linked to Cavallari in October 2020 after the pair were spotted kissing in Chicago. “Kristin and Jeff’s relationship is super hot and fiery right now,” a source told Us in November 2020, pointing out that the relationship is a “casual dating situation.” The following month, the duo were seen packing on the PDA during a trip to Mexico. Us confirmed in March 2021 that Dye and Cavallari pulled the plug on their romance.

Us confirmed in August 2021 that Cavallari was “casually” dating the country singer. Two months later, the Little James founder commented on her relationship status via an Instagram Q&A, revealing that she had been dating “in a general sense,” but wasn’t in a full-on relationship. “No one serious though — I’ve just been having fun,” she said in October 2021. “I haven’t wanted a boyfriend. But I’m currently not dating anyone.”

Cavallari became Instagram official with the model in February 2024 after spending time together in Mexico. “He makes me happy 🤍,” she captioned a cozy picture with Estes, who is 13 years her junior.

Us confirmed in September 2024 that Cavallari and Estes split after seven months of dating.

Cavallari hinted that she was dating a professional athlete by referring to herself as a “f***ing WAG through and through” during a December 2024 episode of the “Dumb Blonde” podcast. Though she didn’t share his name, Cavallari shared that her new romantic interest was in his 40s, had kids from a previous relationship and retired from his sport “a couple of years ago.”

That same month, a source exclusively told Us that Cavallari was “going out with someone, but its not serious,” and that she was dating “multiple people” following her and Estes’ split.

Shortly after Cavallari shared that she had returned to dating apps on a March 2025 episode of her “Let’s Be Honest” podcast, she confirmed the identity of her “deep” fling was former NHL star Nate Thompson.

“I don't even care. I said his name on [my podcast] tour,” she told her podcast listeners in April 2025. “I really think he's such a great guy.”

Noting that the pair were “mostly long distances” throughout their brief relationship, Cavallari went on to state that she’s looking for someone with “compatibility” and “chemistry.”

“I understand what I'm looking for is rare. I get that. … I'm just not gonna settle for anything less than exactly what I want,” she said.

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