Kristin Cavallari's Dating History: A Complete Guide (2024)

From reality stars to NFL athletes, Kristin Cavallari has had her fair share of high profile romances over the years.The TV personality rose to fame on MTV's Laguna Beach, which documented the dramatic lives of a handful of teens growing up in California. When the reality series began in 2004, it followed her on-off romance with Stephen Colletti, and the love triangle between them and costar Lauren Conrad became a central theme of the show.In her 2016 memoir, Balancing in Heels, the Uncommon James founder reflected on the way her relationship changed when the high schoolers were thrust into the spotlight. "Stephen was the most important thing in my life, and there was nothing I cared about more," she wrote. "I hated fighting with him on camera because it felt like I was airing all our dirty laundry."Throughout her time on Laguna Beach, Cavallari got involved with two more reality personalities: Talan Torriero and Matt Leinart, who would later go on to play in the NFL. Each relationship was short-lived, but the reality stars remained close over the years.As she grew more and more famous, rumors about Cavallari's love life began to make headlines. The Very Cavallari star was linked to huge names like Nick Lachey and Chris Evans in the mid-2000s, but later denied that she was anything more than friends with the Hollywood hunks.[sendtonews type="float" key="m0JMycKAAU-3113094-14453"]It wasn't until 2010 that Cavallari found a true love with Jay Cutler. The pair dated for three years before tying the knot in Nashville in July 2013. Over the next seven years, the pair weathered a number of ups and downs, eventually causing them to "come to a loving conclusion to get a divorce" in April 2020."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," the former couple wrote in a joint statement on their individual Instagram accounts at the time, referring to their three children: sons Camden and Jaxon, and daughter Saylor.Though a source explained to Us Weekly that "nothing scandalous or suspect" occurred between them, Cavallari and Cutler's split quickly turned messy, with the fashion designer seeking primary custody of their children and claiming the retired athlete took part in "inappropriate marital conduct."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.

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 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 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.”

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