Kristin Cavallari and Mark Estes’ romance initially surprised the internet.
The Laguna Beach alum sparked dating speculation in February 2024 when she was spotted alongside Estes in Mexico, per a snap obtained by TMZ. Cavallari made headlines later that month when she debuted her relationship with the Montana Boyz member, who’s 13 years her junior. “He makes me happy 
,” Cavallari wrote via Instagram at the time.
Despite the public chatter about their May-December romance, a source exclusively told Us Weekly in March 2024 that Cavallari “doesn’t care” what people think when it comes to his age.
Cavallari and Estes’ relationship also got the stamp of approval from her inner circle. “After seeing them together, they realize Kristin and Mark have a genuine connection, and they see how happy he makes her,” another insider shared at the time.
A third source, however, confirmed to Us seven months later that Cavallari and Estes split.
Prior to her relationship with Estes, Cavallari was married to former NFL player Jay Cutler for seven years before they separated in 2020, finalizing their divorce two years later. They share sons Camden and Jaxon as well as daughter Saylor, whom they welcomed in 2012, 2014 and 2015, respectively.
Scroll down to revisit Cavallari and Estes’ full relationship timeline:
A Complete Guide to Kristin Cavallari’s Dating History
September 2023
Cavallari and Estes’ love story began after she saw him on TikTok.
“Back in like September, I’m scrolling and I come across this boy group, I guess you could call them, The Montana Boyz,” she said on her “Let’s Be Honest” podcast. “So I go, ‘Holy s—t, who are these guys? Because they’re so hot. Specifically this one, who I’m gonna refer to as ‘Montana.’”
Cavallari said she received a message from the Montana Boyz’ account that said “I love you,” and she invited the group to be on her podcast.
She noted that months went by and they began talking. “That attraction was always there, but when I met him, I was like, he’s actually a really nice, good guy,” she said. “He’s very sweet from the jump. He was so sweet to me.”
February 2024
After sparking dating rumors while vacationing in Mexico, Cavallari and Estes took their relationship public when she posted a selfie of the pair on Instagram.
One day after hard-launching her romance with Estes, Cavallari shared a spicy message via her Instagram Story. “You can be as naughty as you want just don’t get caught,” the note read.
She later explained that posting about the romance via Instagram wasn’t always part of the plan.
“I would say it was a little early to hard launch someone, 100 percent. However, what we’ve been talking about, I feel very different with this man,” Cavallari said during an episode of her “Let’s Be Honest” podcast. “But also, I got a call from my publicist that TMZ was going to write an article about us. … I’ve been in this business for 20 years. The media has always controlled the narrative to a large degree. And part of me was like, ‘I want to take it in my own hands.’”
Kristin Cavallari Through the Years: From ‘Laguna Beach’ to Mother of 3
March 2024
Cavallari explained that her relationship with Estes wasn’t something that she was originally intending. “Me dating a 24-year-old is not something that I was searching out. It’s not something that I at all ever thought would ever happen,” Cavallari said on her “Let’s Be Honest” podcast. “I understand what it looks like to the outside world. I really do. I get that. He is not a typical 24-year-old.”
Cavallari revealed that she had introduced her new beau to her children, gushing that her kids were “big fans” of Estes right off the bat. “I think, more than anything, my kids are really excited for me,” she said.
Cavallari also addressed the age gap criticism, noting that “age is just a number.” She added, “It’s what you’ve been through in your life, how you were raised. There are just so many factors that go into maturity other than age.”
She admitted that “the age thing was a hang-up” at first. “Now, I don’t give a f–k and I’m all in with this guy, and I don’t care what anybody thinks,” she said.
The criticism also didn’t seem to phase Estes. “She makes me happy, I make her happy,” he told E! News during an interview with fellow Montana Boyz members Kaleb Winterburn and Kade Wilcox. “That’s what’s important.”
He added, “I’m not too worried about the critics, honestly.”
April 2024
Cavallari admitted that she “mulling over” the idea of having a kid with Estes during an episode of her “Let’s Be Honest” podcast. “If he ends up being The One, like, I would have a kid,” she shared. “It’s become pretty serious, this relationship, I would say.”
Estes, for his part, told Entertainment Tonight that he and Cavallari were “just kind of going with the flow right now,” adding, “But we definitely have had the talk, obviously.”
In an exclusive interview with Us, Estes — who snuggled up with Cavallari at Stagecoach that same month — described their relationship as “as serious as it gets.’
June 2024
Estes joined Cavallari and her three children for a family vacation. “Bahamas with my favorite people 
,” she captioned an Instagram carousel of trip pics, which included shots of her and Estes snuggling up on a boat and her sitting on his lap while laughing.
August 2024
Estes and Cavallari twinned in monochrome white looks while posing for sweet pics in front of a sunset. Estes captioned the Instagram pic with the Greek translation for “I love you.”
September 2024
Us confirmed that Cavallari and Estes broke up. On September 27, the Hills alum appeared at Alex Cooper’s live “Unwell” podcast taping and revealed that the split was recent.
