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:
Stephen Colletti
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.”
Talan Torriero
The Laguna Beach costars hooked up in the early days of the reality series.
Matt Leinart
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.
Brody Jenner
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.
Nick Lachey
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.
Nick Zano
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.
Chris Evans
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.
Justin Bobby Brescia
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.
Miguel Medina
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.”
Jay Cutler
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.
Jeff Dye
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.
Chase Rice
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.”
Mark Estes
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.
