Kristin Cavallari’s dating history: Stephen Colletti, Jay Cutler, more

Kristin Cavallari has been dating in the public eye since she was 17 years old.

The “Laguna Beach” alum shot to fame when reality TV cameras entered her high school, and her dating life quickly began making headlines.

From her teenage romance with Stephen Colletti, to her nine-year marriage to Jay Cutler, look back at everyone Cavallari has dated through the years.

Stephen Colletti

Kristin Cavallari’s first high-profile romance was with Stephen Colletti. Getty Images for IMG

Cavallari and Colletti’s high school romance was documented on the hit reality show “Laguna Beach” in 2004.

Their ups and downs have been memorialized on the MTV series, which ran for three seasons until 2006, but the relationship didn’t last.

The former couple reunited years later when they began hosting a rewatch podcast, “Back to the Beach.”

She told Page Six in May 2022 that the former flames got “really close” while working together again.

Their romance was documented on “Laguna Beach.” FilmMagic

“But no, I mean, you know, there’s nothing romantic happening with us,” Cavallari insisted.

She also apologized to her ex after cheating on him during their tumultuous on-again, off-again romance.

“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–ked up, and I’m sorry,” she said in a 2023 episode.

Talan Torriero

While filming the reality show, she was also romantically involved with Talan Torriero. WireImage for Kohl's

Cavallari cheated on Colletti with their co-star Talan Torriero, who was also having a fling with Lauren Conrad at the time.

“I don’t remember cheating on you. I know that we had talked about maybe I did with Talan,” she told her former boyfriend on their podcast.

“Other than Talan, I don’t think I ever cheated on you with anybody else,” she added.

Torriero was also involved with their co-star Lauren Conrad. WireImage

When Conrad appeared as a guest on the pair’s podcast, the “Hills” star admitted she was also “hooking up with Talan.”

Cavallari laughed, “We all were.”

Matt Leinart

She dated future NFL player, Matt Leinart, in her late teens. J. Vespa

The Uncommon James founder dated football player Matt Leinart when she was 18.

She began romancing the USC quarterback while filming the second season of “Laguna Beach,” however she didn’t divulge his surname at the time.

“Matt is the nicest human being on the planet. He is such a great guy,” she recalled on her podcast.

“He was a five-year senior at USC. He was on top of the world that year.”

After their relationship, Leinart went on to the NFL, where he played for the Arizona Cardinals, Buffalo Bills, Houston Texans and Oakland Raiders.

Brody Jenner

Cavallari and Brody Jenner dated before starring on “The Hills” together. FilmMagic They briefly re-connected in 2021 while filming “The Hills” reboot. John Shearer

Cavallari and Conrad share another high-profile ex: Brody Jenner.

Before “Laguna Beach” spinoff series “The Hills” began, Cavallari dated the son of Caitlyn Jenner for about a year. Their relationship eventually fizzled out.

They reconnected over a decade later when she made a brief appearance on “The Hills: New Beginnings” reboot in 2021.

“She really pulls things out of people; she’s so good at that. She’s such a pro in this industry and in reality television. I mean, she’s been doing it since she was a little kid, forever. So she just adds a lot to it,” Brody said of his ex at the time, noting it felt like “no time” had passed.

Nick Lachey

She briefly romanced Nick Lachey. Kristin Cavallari/Twitter

The TV star was briefly linked to 98 Degrees member Nick Lachey after his infamous split from Jessica Simpson in 2006.

Though their romance was short-lived, the pair seem to be on good terms.

When she was a guest on Lachey’s “Big Morning Buzz” show in 2014, they shared a laugh over the fact that they both —unknowingly — had children named Camden.

Nick Zano

Cavallari hit the red carpet with her short-lived beau, Nick Zano. WireImage

Cavallari also had a short-lived romance with “What I Like About You” star, Nick Zano, from 2006 to 2007.

At the time, Page Six reported that the California native got a tattoo of his initials on her wrist.

When asked about the ink, Cavallari “got really giggly and started blushing,” a spy told us in 2007.

After they called it quits, she got the tattoo removed.

Justin Bobby Brescia

Cavallari’s on-screen romance with Justin Bobby was mostly for show, it was later revealed. Alamy Stock Photo

One of Cavallari’s most prominent storylines on “The Hills” was her love triangle with Justin Bobby Brescia and Audrina Partridge.

However, Partridge later claimed it was all fabricated for the cameras, telling People in 2022 that Brescia “worked with the show to manufacture a relationship with Kristin to keep him in the public eye.”

“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 added.

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Jay Cutler

Cavallari began dating her future husband, Jay Cutler, in 2010. Instagram

Cavallari fell in love with NFL player Jay Cutler in 2010 and he popped the question after just eight months of dating.

She married the former Chicago Bears quarterback in June 2013 and the pair welcomed three children throughout their marriage.

In April 2020, the couple announced in a joint statement that they were calling it quits “with great sadness.”

The “Very Cavallari” star has been candid about her divorce in the following years, even revealing that their separation was “the best thing [she’s] ever done.”

The couple welcomed three children throughout their nine-year marriage. Getty Images

However, she explained that she does not “regret anything at all” and is “thankful for [their] time together” because they share three children together: sons Camden and Jaxon, and daughter Saylor.

Reflecting on her decision to divorce the athlete, Cavallari said it was “really scary” and took her “a few years to actually pull the trigger.”

“It was just time,” she said on the “Call Her Daddy” podcast in 2023.

“Nothing major happened. At the end, it was just time. … It’s the scariest thing. It’s always the saddest thing. I mean, it’s so many emotions, but it can also be the best thing.”

Jeff Dye

Cavallari moved on with comedian Jeff Dye after her separation from Cutler. DIGGZY / SplashNews.com

Following her divorce from Cutler, Cavallari was linked to comedian Jeff Dye.

The pair were seen kissing in October 2020, however it was a “casual dating situation,” a source told Us Weekly at the time.

“Kristin and Jeff’s relationship is super hot and fiery right now,” the insider added.

The following month, the pair jetted to Mexico together, where they were seen packing on the PDA.

However, it seems their romance eventually fizzled out after a few months.

Chase Rice

She casually dated country musician Chase Rice. chaserice/Instagram

Cavallari was briefly linked to country hitmaker Chase Rice in August 2021.

It was reported that the pair were “casually dating,” however the reality TV alum clarified her relationship status on Instagram two months later.

When a fan asked if she was in a relationship, she responded, “No one serious … I’ve just been having fun. I haven’t wanted a boyfriend. But I’m currently not dating anyone.”

Tyler Cameron

The blond beauty revealed she slept with Tyler Cameron. WireImage

In November 2023, Cavallari spoke out about the “hottest” guy she’s ever hooked up with.

“Tyler Cameron and believe it or not, you guys — I know this is really freaking hard to believe — he’s hotter in person,” she said on the “Let’s Be Honest” podcast.

“It’s insane. It’s insane. So yeah, TC for you baby.”

She didn’t divulge when the tryst took place, however the two were seen getting hot and heavy while shooting an Uncommon James campaign in April 2022.

Mark Estes

Cavallari was romantically tied to Mark Estes, who is 13 years younger than her. Instagram/@markestes Cavallari and Estes confirmed their relationship in March 2024. kristincavallari/Instagram

In February 2024, Cavallari went Instagram official with Mark Estes, who is 13 years her junior.

“He makes me happy,” she captioned a photo of the pair posing for a selfie in Los Cabos, Mexico. 

Estes also shared a TikTok video where the two packed on the PDA by kissing, hugging and even clinging to each other.

A source told Page Six at the time that the two “aren’t official yet,” though they’ve “been talking” for several weeks. 

She even introduced her beau to her kids. markestes/Instagram Cavallari later gushed that Estes was the “best sex” she had ever had. Kristin Cavallari/Instagram

“Kristin thinks Mark is super hot. He’s very flirtatious, and she’s loving it,” the insider said. “They were down in Mexico for just a few days but had a lot of fun together. It’s still new.”

Estes is a Montana native who used to play football for Montana State University and Montana Tech and is based in Nashville, Tenn.

The two ended up confirming their relationship by March and went strong for seven months. They even shared some intimate details from their relationship –– including that he wanted kids with her, he met her kids before their first date and that he was the “best sex” she’s ever had –– but they called it quits in September 2024.

“It’s hard because I broke up with Mark because I just know long-term it’s not right, and it’s not because of love lost or something bad happened,” she said on an Oct. 1, 2024 episode of her podcast, “Let’s Be Honest.”

Cavallari broke up with Estes in September 2024. kristincavallari/Instagram Cavallari later confirmed that their age gap played a role in the breakup. kristincavallari/Instagram

“He’s been the best boyfriend I’ve ever had. I just know long-term he needs to experience life, he’s young… I started to feel the age a little bit with life experience,” she confessed.

Cavallari emphasized that their relationship was “very mature” and she does “not regret anything” about their romance.

“It was such a good, happy relationship. And I think with every relationship you learn and you grow from, and I will forever look back at Mark and I with such fond memories and just pure happiness,” she said.