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Kristin Cavallari and Mark Estes’ Complete Relationship Timeline

Feature Kristin Cavallari and Mark Estes Complete Relationship Timeline
Kristin Cavallari and Mark Estes Courtesy of Kristin Cavallari/Instagram

Kristin Cavallari and Mark Estes’ romance may have surprised the internet, but they’re still going strong.

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.

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 for more of Cavallari and Estes’ relationship timeline:

Kristin Cavallari s Complete Dating History From Reality Stars to NFL Athletes 109

Related: 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.”

Kristin Cavallari and Mark Estes Complete Relationship Timeline 3
Courtesy of Kristin Cavallari/Instagram

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 3 111

Related: 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.”

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