Kristin Cavallari, a familiar face in the public dating scene, has experience navigating relationships under the spotlight. The mother of three has had connections with several well-known figures, including her lengthy marriage to former NFL quarterback Jay Cutler.
Most recently, she ended a seven-month relationship with TikTok star Mark Estes in September 2024. The Laguna Beach alum also stirred interest with a TikTok video on November 17, where she hinted at a previous romance with country singer Morgan Wallen.
On her podcast Let’s Be Honest in November 2024, Cavallari revealed she is cautiously reentering the dating scene but is now seeking a more committed relationship.
“I’m serious, my next boyfriend is going to be my next husband,” she declared. “I can’t keep dating indefinitely. I am dating, but I need to find something lasting.”
Reflecting on Cavallari’s Romantic History Provides Insight into Her Past Relationships.
Stephen Colletti was an important figure during Cavallari’s teenage years on the early 2000s MTV series Laguna Beach, where they had an on-again, off-again romance.
After concluding two seasons of the show, the couple eventually parted ways but have remained in touch. They even co-hosted a podcast in 2022 titled Back to the Beach with Kristin and Stephen, during which they disclosed that their relationship predated MTV’s filming by a year.
While it appeared she was exclusively involved with Colletti, Cavallari later confessed to a romantic connection with cast member Talan Torriero.
In a November 2022 episode of Back to the Beach, she and Conrad confirmed they were “hooking up” with Torriero, who humorously acknowledged this with a TikTok video lip-syncing Taylor Swift’s “Anti-Hero.”
At 18, Cavallari dated former NFL quarterback Matt Leinart. Though their relationship lasted only half a year during her senior year of high school, she described him as a close friend and praised him as “the nicest human being on the planet” during a January 2023 podcast episode.
A brief relationship with Brody Jenner occurred while Cavallari was in her early twenties. They later rekindled their friendship on The Hills, where they hinted at a potential romance.
When Cavallari made a guest appearance on The Hills: New Beginnings in 2021, Jenner remarked to PeopleTV’s Reality Check about her contributions to the show, saying, “She’s a pleasure to be around, but she’s a firecracker.”
Even though Justin “Justin Bobby” Brescia’s involvement with Audrina Patridge was often highlighted during The Hills, Patridge speculated about his interest in Cavallari as well.
In her memoir Choices: To the Hills and Back Again, she suggested that Brescia’s relationship with Cavallari began as fabricated but evolved into genuine feelings. Both Cavallari and Brescia denied being in a romantic relationship during a 2009 interview with the Los Angeles Times.
Cavallari also briefly dated cameraman Miguel Medina while filming The Hills. In an episode of her 2018 reality show Very Cavallari, she disclosed that their romance was kept secret from the crew until they were caught by paparazzi at an airport in Canada. “Nobody knew because I’m a professional, and we kept it under wraps,” she shared on the show. “But it was fun.”
Her relationship with Jay Cutler began in 2010. They became engaged in 2011, but Cavallari later revealed in her 2016 book Balancing in Heels that she ended the engagement due to a need for changes. Later that year, they reconciled and announced their first child, Camden Jack Cutler, was on the way in January 2012.
The couple married on June 7, 2013, and welcomed two more children: Jaxon Wyatt Cutler and Saylor James Cutler. In April 2020, Cavallari announced their divorce after a decade of marriage, citing “irreconcilable differences” and “inappropriate marital conduct” in her divorce filing.
“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 stated in an Instagram post. “This is just the situation of two people growing apart.”
Following her split from Cutler, Cavallari was seen getting cozy with comedian Jeff Dye in October 2020. The two were photographed together until February 2021, including a trip to Mexico. However, sources indicated that their relationship lacked exclusivity, despite them exchanging “I love you’s” during an Instagram Live in January 2021.
In September 2021, Cavallari was seen on a date with country singer Chase Rice in Nashville. A source informed PEOPLE that the two had been together for “a little over a month” after meeting through a mutual friend. However, she later told her Instagram followers that she had “no one serious” in her love life.
Cavallari’s relationship with Mark Estes began with a strong social media announcement in February 2024, but ended in September 2024.
She attributed their split to their 13-year age difference, stating, “He’s been the best boyfriend I’ve ever had,” adding that long-term, he needed more life experiences and that she began to feel the age difference.
Rumors about a romance with Morgan Wallen circulated in September 2023. During a Watch What Happens Live appearance, she declined to identify the celebrity her children were fond of.
Although she never confirmed dating Wallen, she hinted at their connection with a TikTok video in November 2024. In this clip, which was part of the “Suspect Challenge” trend, her friend Justin Anderson humorously stated: “Suspect let Morgan Wallen hurt her feelings and she kept going back,” to which Cavallari laughed.
On Bunnie XO’s podcast Dumb Blonde in December 2024, Cavallari discussed the rumors surrounding her and Wallen once more. While she described Wallen as a “good guy” with a “big heart,” she humorously claimed, “He’s been with every woman on the planet.”
Regarding their date, she mentioned, “He was good in bed,” and noted that he had been a “true gentleman” on their first outing and met her children that evening.
When Bunnie XO brought up Anderson’s comments about Wallen, Cavallari clarified that he hadn’t truly hurt her feelings, sharing, “He was the first guy in my life that wasn’t just completely enamored with me … It really threw me. I love having the upper hand, and I feel like with him I didn’t have the upper hand.”
In the same TikTok video, Anderson playfully suggested that Cavallari had a secret hookup with actor Jason Statham, stating: “Suspect’s hottest hookup that she’s never told anybody about was with Jason Statham.”
Cavallari merely laughed at the claim, while Statham, who has been in a long-term relationship with supermodel Rosie Huntington-Whiteley, has yet to comment on the alleged affair.
