Kristin Cavallari Is Dating a Younger Man — Let's Take a Look at Her Relationship History

If you’re a superfan of MTV’s hit show The Hills, chances are you’ve been keeping up with Kristin Cavallari. We all know her for being dubbed as a “maneater” and famously feuding with Lauren Conrad. Kristin has been in and out of the tabloids over the years, and the main focus has always been her dating life.

While her dating history first started on Laguna Beach: The Real Orange County with Stephen Colletti, she has had her share of star-studded relationships with a slew of men. While some romances were more drama-filled than others, they have made quite the conversation pieces for fans of the star. From rumored fake relationships to making things official with a tattoo, Kristin's love life is just as interesting as you could imagine. Keep reading to get all the details.

If you think back to the drama that took over the small town in Orange County, Kristin and Stephen's relationship was a big chunk of it all. While there is no doubt that they made a gorgeous couple, the love triangle between them and Lauren was pretty intense. 

If you remember, Kristin and Stephen's issues in their relationship stemmed from his friendship with Lauren. Kristin felt that Lauren was trying to move in on Stephen whenever they would have a falling out and it didn't help that Stephen was clearly going back and forth between the two ladies. 

However, despite the drama with rumors of infidelity, Kristin and Stephen remained solid once he graduated. But things came to an end as Kristin wanted to be single during her senior year. Thankfully, they still remain close friends to this day.

While Stephen was devastated that his relationship with Kristin was over, it didn't put a stop to her dating life. After all, you can always count on Kristin to have a new boy toy in rotation. And on Season 2 of Laguna Beach: The Real Orange County, viewers heard a lot about Matt —especially since Stephen was upset about her new relationship.

According to ET, "Matt turned out to be Matt Leinart, USC's star quarterback who would go on to play in the NFL." Small world! Kristin frequently used to talk on the show about how hot Matt was and how happy that she was no longer with Stephen.

And naturally, viewers wanted to see Matt make an appearance on the show. However, the time never came. See, the pair eventually split after dating for a few months.

Brody, Brody, Brody! There is a reason why Kristin couldn't get enough of the reality star. After being introduced to him by her former Laguna Beach: The Real Orange County co-star Talan Torriero, the two were joined at the hip. However, there was a lot of controversy that surrounded Brody and Kristin on The Hills.

Cheat Sheet reports, "The only time Brody and Kristin really dated was before the show ever started." And the news came as many rumors persisted that the drama — including the relationships on the show — were fake.

Us Weekly also reported that while Brody did admit that he never really dated many of the women on the show, his relationship with Kristin was the real deal. The only thing is that they never actually dated on the show. "The pair dated prior to her stint on the show and their reconciliation was entirely fabricated for the cameras," the site shared. 

Kristin was never the type of girl to allow a break up to keep her down. And after things between her and Brody ended, she moved forward with the What I Like About You star.

Kristin was reportedly very serious about Nick. The two were frequently photographed with one another and appeared very much smitten with one another.

In fact, Kristin even took things to the next level by getting Nick's initials tattooed on her wrist. But as the saying goes, "All good things come to an end." The couple later split in December 2007 and Kristin later got the tattoo removed. 

Kristin has been very vocal over the years about how fake reality television can be. And while she was linked to people that she never really dated, she actually was coupled up with Miguel, who worked on The Hills. 

While the two were eventually spotted out together, Kristin revealed that she actually kept their relationship a secret in the beginning. "We dated for a few months and nobody knew," she explained on Very Cavallari. "And I was dating Brody on the show and like, meanwhile, Miguel was, like, filming it." Very uncomfortable!

She also explained that they got found out after the paparazzi caught them at the airport. And while they did have a fun run with one another, things came to a natural end in 2009.

There's no denying that Kristin is a tough nut to crack. And while it may be easy for athletes to date pretty much any woman they want, Jay had to put in a lot of work to wear Kristin down.

According to Insider, after initially turning down Jay's request to fly her out to Chicago, the two eventually met when she attended a preseason game in 2009. 

"We hung out two nights later, and that began a swift and intense romance. I flew back to Chicago at least every two weeks," Cavallari wrote in her book Balancing in Heels: My Journey to Health, Happiness, and Making It All Work. 

"When we were apart, we texted constantly, and he wrote me the sweetest love emails. He was the strong, manly man I wanted but had a sweet, romantic side as well," she continued.

Eventually, the couple moved forward with their relationship and got engaged in April 2011. And while Kristin called off the engagement after three months, they got back together in November 2011. 

The two went on to have their first child, Camden, in August 2012. They finally jumped the broom in June 2013. Kristin and Jay welcomed another son, Jaxon, in May 2014 and finally welcomed baby girl, Saylor, to their family in November 2015. 

While the couple continued to be blissfully in love and even shared their life with fans on the show Very Cavallari, things eventually took a turn. Cheating rumors on Jay's behalf persisted with Kristin's friend Kelly Henderson, although he denied stepping out on the star. And eventually, the couple shared news of their divorce in April 2020 on Instagram. 

Divorce should never get in the way of finding love with another, and Kristin is a firm believer in the fact. And while the star took some time to herself after splitting up with Jay, she eventually found a new man.

After being spotted locking lips with Jeff, fans believed that the two were an item. According to US Weekly, they were never an official couple, despite being spotted together engaging in public displays of affection multiple times. The pair split after just five months of casual dating.

Although the two were confirmed to be dating in August 2021, Kristin claimed that they weren't in a real relationship two months later. According to an Instagram Q&A, she was dating in the general sense but wasn't dating seriously.

Kristin posted a picture of herself and Mark Estes enjoying time in Los Cabos, Mexico. The caption said, "He makes me happy 🤍." Mark is 13 years younger than Kristin. He was a football player at Montana State University as well as Montana Tech.

Some fans questioned the age difference between Kristin and her new boyfriend, leaving some backlash in the comments. One Instagram user, @taelor013, commented, "What could a 37 year old and a 24 year old possibly have in common." Another person, @theechelsey, joked, "She's finally posting pics of her kids." Other people came to Kristin's defense, posting about their own age-gap relationships and saying that they do actually work despite the age difference.

Kristin is usually tight-lipped when she starts dating someone, so its a big deal that she posted about Mark on her Instagram main feed. Only time will tell whether they will go the distance.