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Kristin Cavallari has very much grown up in the spotlight! As a junior in high school, she was part of the cast of the first season of Laguna Beach: The Real Orange County. Throughout the series, her friendships, relationships, and other high school escapades were chronicled. Over the years, Kristin, 37, has been a part of many reality series, including The Hills. She’s also dabbled in acting in small films, such as National Lampoon’s Van Wilder: Freshman Year.
With so much of her life occurring on reality TV, Kristin’s relationships have also garnered much interest over the years. From her romance with her high school boyfriend Stephen Colletti to her marriage to Jay Cutler. In September 2023, a fan asked her about “hints” on a celebrity that she went out with, because her kids were fans during an appearance on Watch What Happens Live. Host Andy Cohen chimed in to mention that she’d already alluded to her kids loving a certain country star. “It’s obviously Morgan Wallen. She just said her kids are big fans of his,” he quipped.
Kristin’s eyes widened, and she laughed at the awkwardness. “I’m not answering that question,” she said, before dodging one of Andy’s follow-up questions. “I’m not dating him.” Andy asked if she went on “a date” with the “Last Night” singer, and she responded, “I don’t know.”
In February 2024, Kristin confirmed she was dating Mark Estes, a model on TikTok.
Look back on Kristin’s romances over the years here.
Stephen Colletti
When the world was introduced to Kristin on Laguna Beach in 2004, she was dating her high school sweetheart Stephen Colletti. The two teens’ on-and-off romance was a huge focal point for the reality series, and the show tracked their relationship and her then-rivalry with Lauren Conrad. Like many high school romances though, Kristin and Stephen ultimately broke up.
Despite breaking up, Stephen and Kristin are clearly on good terms once again! Shortly after Kristin split from Jay Cutler, she posted a photo of the two of them cuddling in 2020, sparking many reunion rumors. While they did not get back together, they have collaborated quite a few times in recent years, including on their Back to the Beach podcast. In a January episode of the podcast, Kristin gave Stephen an apology over a decade in the making, when they reflected on her cheating on him with the next person on this list back when they co-starred on Laguna Beach. “I am more than willing to own up to this right now, because I have blacked it all out of my memory, which is also really f***** up, and I’m sorry,” she said.
Talan Torriero
Kristin cheated on Stephen with their co-star Talan Torriero on Laguna Beach. “I don’t remember cheating on you. I know that we had talked about maybe I did with Talan” she told her ex on the podcast. “Other than Talan, I don’t think I ever cheated on you with anybody else.”
Kristin revealed that they had a bit of a fling at the same time that Talan was also seeing Lauren Conrad. “I was hooking up with Talan,” Lauren said on an episode of the podcast, per Cosmopolitan. Kristin later admitted, “We all were.”
Matt Leinart
During the second season of Laguna Beach, Kristin also briefly dated football player Matt Leinart. At the time, the quarterback was playing college football for the University of Southern California, but after finishing, he went on to the NFL and played with the Arizona Cardinals, Buffalo Bills, Houston Texans, and Oakland Raiders.
On an episode of her and Stephen’s podcast, she had only good things to say about the football star. “Matt is the nicest human being on the planet. He is such a great guy,” she said, per The New York Post.
Brody Jenner
After Laguna Beach ended, Kristin moved on to The Hills, and she started dating someone else from a family that knows a thing or two about reality TV: Brody Jenner. While Kristin has disputed some details about what on The Hills was factual and what was fabricated, the pair did date for about a year. After the split, the two remained on good terms, and Kristin even wished him and his then-fiancée Kaitlynn Carter well in a 2016 interview with Entertainment Tonight.
When the second season of The Hills: New Beginnings premiered in 2021, Kristin made her return alongside Brody to the beloved franchise. At the time, Kristin told HollywoodLife in an exclusive interview that it was “so fun” to go back. “It was like no time has passed,” she said. “I loved seeing everybody and filming. I did one episode and I’m so happy that I was able to go back and have a good time.”
Nick Lachey
Kristin was briefly linked to 98 Degrees singer Nick Lachey in 2006, but their rumored romance was very short-lived. The two clearly remained positive. When the reality star was a guest on Nick’s Big Morning Buzz show in 2014, they shared a laugh about the fact that they both have children named Camden, which Nick didn’t know, per MTV.
Nick Zano
Another one of Kristin’s short-lived romances was with What I Like About You actor Nick Zano in 2006. She clearly liked him a lot and even got his initials tattooed on her wrist, but they split up in 2007. After they broke up, she went about getting the tat removed, per E! News.
Justin Bobby Brescia
During her time on The Hills, Kristin’s love triangle with Justin Bobby Brescia and Audrina Partridge was a huge storyline in 2009. Despite the drama on the show, Audrina claimed that Justin “worked with the show to manufacture a relationship with Kristin to keep him in the public eye” in her memoir Choices: To The Hills and Back Again, per People.
Audrina further explained that a lot of the drama 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,” she said. “Kristin didn’t want to wait around anymore, so she was there trying to calm me down enough to just film the scene and get it over with. We laughed about it off-camera, but on-camera, we yelled and glared and made it work.”
Miguel Medina
While working on The Hills, Kristin got involved with someone else involved in the show, albeit behind the camera, literally. She admitted she was dating cameraman Miguel Medina in 2010, per Us Weekly. She revealed that some of her romance with Brody Jenner was fabricated for the show, and at the time, she was really dating Miguel, per The Things.
Jay Cutler
Kristin started dating NFL player Jay Cutler in 2010, and they eventually got married in 2013. During the course of their marriage, they had three children, but they eventually split up in 2020. Their divorce was finalized in 2022. Kristin reflected on her decision to split up with Jay in a 2021 interview on the Off The Vine podcast. “I just decided I didn’t want to be in a toxic relationship anymore and I had to break it off,” she said.
While Kristin has spoken openly about her and Jay’s split in interviews, the football player explained that he wasn’t interested in speaking ill about her in a Call Her Daddy interview. “If she wants to say stuff, she can say stuff. I’m not going to go down that road about her. I mean, she’s still the mother of my kid,” he said. In that same interview, he denied rumors that he’d cheated on Kristin.
Jeff Dye
Months after Kristin and Jay split, she started dating comedian Jeff Dye. The couple first sparked romance rumors when they were seen making out in Chicago in October 2020. After just five months together though, it was reported that they had split, and their romance wasn’t that serious.
Chase Rice
After things ended with Jeff, Kristin was briefly linked with country singer Chase Rice in August 2021. Still, the relationship was very short-lived and casual. In October of that year, she revealed that she was single in an Instagram Story, responding to a fan who asked if she was dating. “No one serious, though — I’ve just been having fun. I haven’t wanted a boyfriend. But I’m currently not dating anyone,” she wrote.
Mark Estes
On February 27, 2024, Kristin went Instagram official with model and TikTok star Mark Estes, 24. She posted a smiling photo of the two of them posing during a vacation in Mexico and captioned it with, “He makes me happy.” He also took to TikTok to share a video of the two of them rocking swimsuits and lip synching to Gloriana‘s song “(Kissed You) Good Night.” They also shared a kiss and hug as he picked her up.
