Cavallari began dating Stephen Colletti when she was a sophomore at Laguna Beach High School and he was a junior, according to E! News. The first season of Laguna Beach began filming in the spring of 2004, after they'd been dating for at least a year. Cavallari was finishing up her junior year of high school and Colletti his senior year.

Over the summer of 2004, Cavallari and Colletti found themselves in a love triangle with Lauren "LC" Conrad, which caused them to constantly break up and make up. At the end of Season 1, Colletti left for San Francisco State University. The two tried to make a long-distance relationship work, but they fizzled out before winter break. In Season 2, Colletti tried to win Cavallari back and nearly succeeded on Valentine's Day in 2005... but Cavallari decided they were better off as friends.

In August 2020 — just a few months after announcing her decision to divorce from Jay Culter — Cavallari broke the internet when she posted a current-day picture of herself and Colletti hugging, which she captioned, "2004 or 2020?!" However, she later assured fans she and Colletti aren't rekindling things. "Stephen and I have remained really good friends over the years. I love him to death, but no we're not dating," she told People. "That's the last thing on my mind right now."

As Laguna Beach fans may recall, Cavallari occasionally hooked up with fellow cast member Talan Torriero when she and Colletti were on the outs, but things never got serious between the two.

During the Season 2 premiere of Laguna Beach, it was revealed that Cavallari had begun dating "Matt, this guy at USC" while Colletti was away at college. As it turns out, Cavallari's mystery man was Matt Leinart, USC's star QB who later went on to play in the NFL. However, the relationship only lasted for a few months before Cavallari and Leinart went their separate ways.

The pair briefly sparked reconciliation rumors when they were reportedly spotted together in Vegas in 2008, per E! News, but little else was heard about the exes after that.

After filming for Laguna Beach Season 2 wrapped in 2005, Cavallari began dating Brody Jenner, who she met through Torriero. The couple dated on-and-off-again for nearly a year before calling it quits in August 2006. "Yes, Brody and I broke up," Cavallari confirmed to People soon after. "It's just hard right now because I am working all the time. We're still good friends though."

Year later, Cavallari and Jenner reportedly got back together on the Laguna Beach spin-off, The Hills, but according to Cavallari, the reconciliation was totally fabricated for TV. "Brody Jenner at the time was dating Jayde Nicole," Cavallari explained during a December 2013 appearance on Bethenny. "I dated Brody when I was 18, right after Laguna Beach, actually, and that's it ... They pretended that him and Jayde broke up and I was dating Brody, and Jayde and I got into a huge fight because she saw us in a club. It wasn't real at all. They were together the entire time."

Shortly after her romance with Brody fizzled out, Cavallari reportedly began dating actor Nick Zano, who's best known for the WB sitcom What I Like About You. Things got so serious between the two that Cavallari reportedly got his initials tattooed on her wrist, though — after she and Zano reportedly split in December 2007 — the reality star reportedly got the tattoo removed. "It is kind of painful," a source for E! News reportedly claimed in January 2008, "but she wants that thing off." Cavallari has never commented on their reported relationship or breakup.

While on The Hills, Cavallari seemingly romanced both Brody Jenner and Justin Bobby Brescia on-screen, but IRL, she was dating someone behind the scenes. During a February 2020 episode of Very Cavallari, the reality star told her fellow Hills alums Heidi Montag and Audrina Patridge about her secret romance with cameraman Miguel Medina in 2010. "We dated for a few months and nobody knew," she explained. "And I was dating Brody on the show and like, meanwhile, Miguel was, like, filming it."

The secret romance wasn't made public until paparazzi spotted Cavallari and Medina at the airport together in June 2010, but Cavallari didn't comment on the dating speculation at the time. It's unclear when or why the two split.

According to Cavallari, her publicist first contacted her about Cutler in 2009, saying the Chicago Bears QB wanted to fly her out to Chicago for a date. As she was filming The Hills at the time, she passed. Then, a year later, she ended up going to a Chicago Bears preseason game, having totally forgotten about Cutler's invitation. The two ended up finally meeting and the attraction was instantaneous. As Cavallari later wrote in her 2016 book, Balancing in Heels, "We hung out two nights later, and that began a swift and intense romance."

After just about eight months of dating, Cutler proposed over Easter weekend while he and Cavallari were vacationing in Mexico. Less than three months later, while in the midst of planning their spring 2012 wedding, Cutler reportedly called off the engagement. At the time, a source for Us Weekly reportedly claimed Cavallari was "blindsided" by the decision, but the reality TV star later claimed she was the one to end things in her 2016 book. "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.

It wasn't long before the two reconciled, and by November 2011, the couple confirmed that their relationship and their engagement were back on, with Cavallari tweeting, "This time its official... Jay and I are engaged again." Cavallari and Cutler finally tied the knot in June 2013, and after just about seven years of marriage and a decade together, they announced their decision to divorce in April 2020. Luckily, it seems like things are amicable between the two as they continue to co-parent their three kids: Camden, Jaxon, and Saylor.

Six months after announcing her divorce from Cutler, Cavallari sparked dating rumors with comedian Jeff Dye after TMZ released a video of the two seemingly kissing in Chicago in October 2020. At the time, a source for E! News reportedly claimed the relationship was casual. "Their relationship is very easygoing, and Kristin is not thinking long-term right now and isn't trying to get serious right away," the source reportedly claimed. "She has three children and knows it will have to be a slow process."

Since then, the two have reportedly been spotted on several occasions, though they have yet to comment on their rumored relationship. Most recently, Cavallari and Dye were reportedly seen together in Studio City, California, per Page Six.

Wherever Cavallari and Dye stand, I just hope they're enjoying themselves!