Mark Estes (2024)
Kristen Cavallari most recently dated Montana Boyz TikToker Mark Estes. They started dating after he slid into Cavallari’s DMs accidentally using the Montana Boyz account. “Yeah, I thought I was on my own account and I DMed her,” Estes told People. “We woke up the next day and [my friend] was like, ‘Who DM’d Kristin?’ I was like, ‘Oh, that was me.’”
The pair first became Instagram official in February 2024 when Cavallari posted a photo of them vacationing in Mexico. “He makes me happy 🤍,” she captioned the post, which Estes re-shared on his Instagram Story.
Estes is thirteen years younger than the Hills alum. She addressed the age gap in an episode of her podcast, Let’s Be Honest. “I want you guys to know that me dating a 24-year-old is not something that I was, like, searching out,” she said. “I understand what it looks like to the outside world, I really do. I get that. [Mark] isnot a typical 24-year-old.”
“If you guys listen to the podcast, you know, I thought 30-year-olds were too young for me. I understand what it looks like to the outside world, I really do. I get that,” she added. “When I met him, I was like, obviously I thought he was the hottest guy I’ve ever seen. There was — that attraction was always there. But when I met him I was like, he’s actually a really nice, good guy. He’s very sweet — from the jump, he was so sweet to me. Like the very first thing he said to me when we were standing there and [had] just met, he was like, ‘You’re, like, really pretty.’”
Unfortunately, the pair called it quits seven months after they went official. Cavallari revealed the reason for their breakup on an episode of her podcast. “It’s hard because I broke up with Mark because I just know, long term, it’s not right,” she said. Their split was “not because of love lost or something bad happened, no one cheated, no one was mean.” She continued, “Mark didn’t do anything. Mark has been nothing but so sweet and so supportive and he’s always been there.”
Instead, she attributed their breakup to his age gap. “I just know, long term, he needs to experience life. He’s young and I started to feel the age a little bit just with life experience,” Cavallari said.
Jay Cutler (2010 – 2020)
Kristen Cavallari and Chicago Bears quarterback Jay Cutler were together for a decade. They met in 2010 and got engaged one year later in 2011. After briefly breaking up, the two reconciled and announced that they were having their first child together. They welcomed their son, Camden Jack Cutler, in 2012.
On June 7, 2013,the couple officially tied the knotin Nashville. “Im officially Kristin Elizabeth Cutler!!!!!” Cavallari tweeted after the celebrations. In the next few years, they welcomed two more children, Jaxon Wyatt Cutler and Saylor James Cutler.
However, things started going downhill for the couple in 2020 when Kristin addressed the rumor that her best friend Kelly Henderson and Cutler were having an affair. “When season 2 was airing, there was a lot of talk on social media about Jay and Kelly having an affair,”Cavallari said during the Season 3 premiere of her reality show, Very Cavallari. “Not for one second have I ever thought that it was true. It wasn’t the actual accusations of them having an affair that made me upset, it was how Kelly went about it.”
Shortly after, Cavallari and Cutlerrevealed that they were divorcing 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. The reality TV star later told People that she and Cutler had been struggling in private for years. “I always thought it was interesting when people would refer to us as ‘couple goals,'” she said. “I was like, ‘If you guys only knew.'”
Brody Jenner (2005 – 2026)
One of Cavallari’s most high-profile exes is Brody Jenner, the son of Caitlyn Jenner. The reality TV star revealed that she started dating Jenner when she was 18, right after Laguna Beach. “And then on the show, on The Hills, they had us ‘dating’ for a few episodes,” she said, according to The List.
Unfortunately, their relationship fizzled about one year after they started dating. The pair reunited ten years later when she appeared on the The Hills 2021 reboot, “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. I mean, she’s been doing it since she was a little kid, forever,” Brody said of his ex at the time. “So she just adds a lot to it.”
Stephen Colletti (2004 – 2005)
Cavallari and Colletti dated on and off during high school while starring in MTV’s Laguna Beach, which aired for three seasons until ending in 2006—about a year before their relationship ended. In 2022, they reunited to launch a podcast called Back to the Beach, where they revisit and discuss episodes of the show.
“I love Stephen so much and it’s been so nice to have him in my life again — and we’ve gotten really close,” she told Page Six in May 2022 about working with Coletti again. “But no, I mean, you know, there’s nothing romantic happening with us,” she clarified.
