Kristin Cavallari's Dating History in 14 Clicks: From Stephen Colletti to Mark Estes

Kristin Cavallari started dating in high school, and she detailed her love story with Stephen Colletti on the hit show Laguna Beach in 2004. Their on-again, off-again romance began in 2001 until they broke up for good in 2004.

While starring in the reality TV series, Cavallari reportedly cheated on Colletti with their costar Talan Torriero, who was linked to Lauren Conrad then.

As the affair rumors spread like wildfire, Cavallari spoke about the reported hookup.

"I know that we had talked about maybe I did with Talan," she said on their "Back to the Beach with Kristin and Stephen" podcast. "Other than Talan, I don't think I ever cheated on you with anybody else."

At 18, Cavallari found herself dating football player Matt Leinart when Season 2 of Laguna Beach started filming.

"Matt is the nicest human being on the planet. He is such a great guy," she recalled on her podcast without mentioning Leinart's last name. "He was a five-year senior at USC. He was on top of the world that year."

Cavallari and Brody Jenner had a whirlwind romance for nearly a year between 2005 and 2006. Things eventually fizzled out, but they reconnected on the 2021 show The Hills: New Beginnings.

"She really pulls things out of people; she's so good at that. She's such a pro in this industry and in reality television," said Jenner. "I mean, she's been doing it since she was a little kid, forever. So she just adds a lot to it."

Following Nick Lachey's split from Jessica Simpson, the 98 Degrees member was linked to the blonde beauty for a short time. The dating buzz died down shortly after their short-lived romance.

Cavallari reportedly hooked up with Captain America star Chris Evans in 2008, but she later clarified they were not an item.

"No, we're just friends," she told Us Weekly. "I've known Chris for awhile, just through mutual friends. I've known him for a few years, actually."

On The Hills, Cavallari developed a love triangle involving Justin Bobby Brescia and Audrina Patridge. It was later revealed the scenario was fabricated for the cameras.

"There really wasn't much for me to say to her. I was finished with Justin and I really didn't care if Kristin and Justin were hanging out — especially because I knew it was just for the show," Patridge said.

She added, "Still, production was adamant that we get an explosive scene. So adamant, in fact, that they blocked in my car with production vans and wouldn't let me drive away until I fought with her. I was furious! This was way beyond anything they'd done in the past to get the scene they wanted. I literally couldn't leave."

Cavallari revealed to Patridge and Heidi Montag on Very Cavallari that she dated MTV cameraman Miguel Medina in 2010.

"We dated for a few months and nobody knew," she admitted. "I was dating Brody on the show and like, meanwhile, Miguel was filming it."

While Cavallari's relationships did not last long, she fell in love again with Jay Cutler in 2010. Their romance led to their wedding after three years of dating, only to call it quits in April 2020.

"With great sadness, after 10 years together we have come to a loving conclusion to get a divorce," Cavallari wrote on Instagram.

"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," she went on. "This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family."

Their divorce filing cited "irreconcilable differences" and "inappropriate marital conduct" as the reason behind their split. They also acquired a joint custody agreement after ending their marriage.

Cavallari was pictured kissing Jeff Dye in October 2020 after her divorce. A source said they were only dating casually at the time. They marked more PDA-filled outings, though things seemingly ended quietly after a few months.

In August 2021, Cavallari was linked to Chase Rice and started casually dating him. Two months after the buzz emerged, she took to Instagram to reveal that it was not "in a full-on relationship" as "no one was serious."

Speaking on the "Let's Be Honest" podcast in November 2023, Cavallari called Tyler Cameron the "hottest guy" she had ever been linked to. She did not share when they had a fling, but they worked together on an Uncommon James campaign in 2022.

Cavallari's current beau is Mark Estes, who is one of the Montana Boyz on TikTok.

The pair went Instagram official in February, with Cavallari posting a photo from their vacation in Los Cabos, Mexico.

"They've been dating longer than people think and have kept it very private," a source told People of the relationship. "They're serious enough now that they were ready to go public. They're really happy together. He's been so great to her and is just a really nice guy."