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Inside Kristin Cavallari's Dating History

Kristen Cavallari attends Melodies For Minds Fundraising event in Nashville (2024) Jason Davis/Getty Images

Kristin Cavallari is open when it comes to her love life. She had several short-lived romances with fellow reality stars, athletes, and heartthrobs like 98 Degrees singer Nick Lachey and "What I Like About You" star Nick Zano before marrying former NFL player Jay Cutler. After Cavallari's relationship with Cutler crumbled, she reentered the dating scene and was linked to a string of famous men, including country singer Chase Rice. However, a video shared on the "Laguna Beach" alum's TikTok in November 2024 proved that there are some stories in Cavallari's relationship history that even the paparazzi have yet to uncover.

In their take on the "Suspect Challenge" trend, wherein participants playfully roast each other, hairstylist Justin Anderson called her out over some past celebrity flings, claiming that Cavallari's alleged dalliance with Jason Statham was her "hottest hookup." Cavallari was shocked but didn't immediately refute her friend's claim, which left many of her TikTok followers convinced it was true and had them begging her for details. Another reason why some believed Cavallari did hook up with the "Transporter" star was that in the same video, she appeared to confirm a rumor that first surfaced in 2023 that she had a fling with country superstar Morgan Wallen. While no timelines were given, Cavallari's alleged hookup with Statham, if true, may have happened before he got serious with his now-fiancée Rosie Huntington-Whiteley, whom he began dating in 2009.

While she swore off relationships with men in the public eye during a November 2024 podcast episode, Cavallari's dating history is still dominated by celebrities. Here's a look at her relationships through the years.

Cavallari dated and fake-dated several of her costars but did both with Brody Jenner

Kristin Cavallari and Brody Jenner attend PETA's 25th Anniversary Gala and Humanitarian Awards Show in Hollywood (2005) Gregg Deguire/Getty Images

Kristin Cavallari dated quite a few of her reality TV costars, including her "Laguna Beach" castmates Stephen Colletti and Talan Torriero back in the 2000s. However, she also pretended to be in love with some of them for the cameras, which was the case with her "The Hills" costars Justin "Justin Bobby" Brescia and Brody Jenner. But what's interesting about the latter is that Cavallari had both a real and fake relationship with Jenner.

Before she appeared on "The Hills," which aired from 2006 to 2010, Cavallari dated Brody for about one year when she was 18, as she revealed in a 2020 episode of "Very Cavallari." They later reunited on the "Laguna Beach" spinoff series, where they fake-dated — all while Cavallari's actual boyfriend at the time, MTV cameraman Miguel Medina, captured their sweet moments for the show. "We dated for a few months and nobody knew," she said of her relationship with Medina. "And I was dating Brody on the show and like, meanwhile, Miguel was, like, filming it." According to Cavallari, she and Medina kept their romance so low-key that no one caught on until they were seen together by paparazzi shortly before "The Hills" aired its last episode.

Neither the breakup nor the (fake) love triangle left any lasting ill feelings between Cavallari and Brody. After they reunited on the reboot "The Hills: New Beginnings" in 2021, Brody expressed his excitement over getting to work with her again, telling Page Six, "She's so much fun and so cool to hang with. I think we all love her to death."

Cavallari was married to Cutler for almost seven years

Kristin Cavallari and Jay Cutler smile at Uncommon James VIP Grand Opening at Uncommon James in Chicago (2019) Timothy Hiatt/Getty Images

Kristin Cavallari told "A Drink With" in 2013 that she initially turned down her future husband Jay Cutler when he first asked her out in 2009. However, she changed her mind after she finally met him in person and soon fell hard for his charms. The two briefly split in 2011 but quickly reconciled and went on to tie the knot in 2013 and welcome three children. However, their marriage showed some cracks on "Very Cavallari," with the reality star admitting in 2019 that they "definitely have issues." But Cavallari downplayed them, noting they were normal for a marriage. She also stood by Cutler after rumors spread that he allegedly had an affair with her former best friend Kelly Henderson.

However, Cavallari and Cutler ultimately couldn't overcome their marital problems and announced their split in April 2020, with the former citing alleged inappropriate marital conduct as a reason behind her divorce filing, per People. Following the announcement, the pair decided to go on a few dates to see if there were still some sparks left, but they ultimately pushed through with the divorce and finalized it in 2022. Cavallari later described it to podcast host Lewis Howes as "the best thing that I've ever done."

Cavallari went on to repeatedly slam their marriage as "toxic" in interviews, but Cutler preferred to stay mum on the issue. "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 kids," he said on "Sofia with an F."

Cavallari moved on with Jeff Dye after separating from Cutler

Kristin Cavallari smiles at the 2019 Golden Globe Awards (2019), Jeff Dye attends "Better Late Than Never" Premiere Press Screening in Hollywood (2016) DFree & Featureflash Photo Agency/Shutterstock

Months after announcing her split from Jay Cutler, Kristin Cavallari showed everyone she had moved on when she was spotted kissing her new boyfriend, comedian Jeff Dye, in October 2020, TMZ reported. The pair were loved-up for the next five months, enjoying a vacation in Cabo San Lucas and smooching at a Nashville bar. According to E! News, they said, "I love you," to each other during an Instagram Live in January 2021, sparking rumors that they were getting serious. However, just two months later, an insider told E! News that Cavallari and Dye were over. "It was never that serious to begin with. She was having fun," the source said.

Two years later, Cavallari's relationship with Dye returned to the spotlight after he called her out during an interview for talking about his October 2023 DUI arrest on her podcast, accusing her of using it to drum up publicity. Recalling the incident, Dye, who drank the night before, said he'd been on his way to meet up with Cavallari when he crashed his car. He fled the scene and headed to the coffee shop where he was meeting her but got arrested by officers there. The comedian also claimed on "The Adam Carolla Show" that he had hoped to rekindle his romance with Cavallari at the time but that she allegedly led him on.

Cavallari later fired back at her ex during an Instagram Q&A, pointing out that she "never said his name" when she discussed the incident on her podcast. "He thinks he's tearing me apart, but you just gave me so much press for my podcast," she added.

Cavallari fell in love with much younger beau Mark Estes

Despite having been linked to Jeff Dye and Chase Rice after her divorce, Kristin Cavallari didn't hard-launch any relationship until February 2024 when she debuted her romance with Mark Estes, who is 13 years her junior, on Instagram. She posted a since-deleted photo of them and captioned it, "He makes me happy." While their age difference raised some eyebrows, Cavallari and the TikTok star continued to show off their love, filling their feed with photos of them packing on PDA.

Cavallari revealed on her "Let's Be Honest" podcast that she felt immediate attraction when she spotted Estes in a Montana Boyz video on TikTok. After receiving a DM from the group's account that said, "I love you," which Estes later confessed to sending, the two got talking, and Cavallari found herself falling for the much younger man. Estes also made no secret of how much he adored her. "We just clicked," he told E! News.

Unfortunately, they broke up after seven months, though it wasn't due to any third party or fight. Cavallari explained on her podcast that her age gap with Estes and their vastly different life experiences played a huge role. Though she described him as "the best boyfriend I've ever had," she said she "broke up with Mark because I just know long term it's not right," adding: "I just know long term he needs to experience life." The reality star — who once said she's done having kids — added that she hoped Estes would be able to build a "beautiful family of his own" as she did.

Cavallari is dating a mystery man nicknamed Cody

Kristin Cavallari smiles while out in SoHo in New York City (2023) Gotham/Getty Images

Kristin Cavallari had one major takeaway from her breakup with Mark Estes, and that was to pursue a relationship with someone who is around her age, isn't a celebrity, and would be able to teach her life lessons instead of needing her to guide them. She revealed the shift in her preferences and priorities in an episode of her "Let's Be Honest" podcast two months after her split from the TikTok star. Cavallari also confessed that four years after the end of her first marriage, she was tired of playing the field and ready to settle down again, vowing, "My next boyfriend is gonna be my next husband."

While her comments suggested she had yet to find someone she wanted to be in a serious relationship with, Cavallari shared that she was casually dating a man who might fit the bill. She didn't drop his name, only dubbing him as "Cody," but did share a few details about her new suitor. "He's not on social media. He's a businessman, and I love that," she said, adding that she "met him in real life" rather than online like some of her past beaus.

Aside from him not being part of the entertainment industry, Cavallari said she appreciates that Cody "feels a lot older to me" despite being the same age as her. She explained that she'd been "really wanting someone older who I can, like, learn and grow from" following her failed marriages and relationships.

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