Kristin Cavallari sure knows how to pick ’em!
Over the years, the reality star dated quite a few hunky guys, including her Laguna Beach co-star Stephen Colletti, singer/actor Nick Lachey, and most recently, NHL hottie Nate Thompson. You sadly won’t find Chris Evans or Justin Bobby‘s names on the list, though! She debunked those rumors earlier this year! LOLz! But don’t worry! There are still plenty of other big-name celebrities in her dating history! There are even some huge shockers! Ch-ch-check out all her past romances below…
Related: Kristin Cavallari & Harry Jowsey Tell The Whole Truth Behind ‘D**k Pic’ Story!
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Stephen Colletti
Ahh, young love! When Kristin rose to fame as a teenager in 2004 on the MTV show Laguna Beach, she famously was in an on-and-off relationship with her co-star Stephen Colletti! They began dating a year before the series started filming, but once cameras were up? Drama ensued, all thanks to the love triangle with Lauren Conrad! And because she cheated on him a few times, including once with their co-star Talan Torriero. Oof.
After two seasons, Kristin and Stephen broke up for good. Although their love didn’t make it out of high school, they managed to maintain a friendship. They even had a Laguna Beach recap podcast called Back to the Beach with Kristin and Stephen.
Talan Torriero
As mentioned above, Kristin wasn’t only romantically involved with Stephen on Laguna Beach! She also got with Talan! During a November 2022 episode of Back to the Beach, the podcast host admitted she was “hooking up” with her co-star! And Kristin wasn’t the only one! Lauren was, too! Those two were so messy back then! LOLz!
Matt Leinart
Eventually, Kristin took a break from dating her castmates and moved on to Matt Leinart during Season 2 of Laguna Beach. She was a senior in high school, and he played football at the University of Southern California. Their relationship didn’t last long, though! They broke up after six months but remained close afterward! She shared on the Back to the Beach pod:
“I’m actually still good friends with Matt. Matt is the nicest human being on the planet. He’s such a great guy. But yeah, I dated him when I was 18, my second half of my senior year. He was a five-year senior at USC. He was on top of the world that year. I was so excited about it, clearly, like, no chill whatsoever. But it was a big deal for me.”
They didn’t work out, but at least she gain a longtime friend after the relationship!
Brody Jenner
Kristin dated Brody Jenner shortly after her time on Laguna Beach. They met through Talan and were together on and off for almost a year until they broke up in 2006. She told People at the time:
“It’s just hard right now because I am working all the time. We’re still good friends though.”
They later rekindled their romance on The Hills — though Kristin admitted it was all fake! She spilled on Bethenny in 2012:
“I dated Brody when I was 18, right after Laguna Beach, actually, and that’s it. And then on the show, on The Hills, they had us ‘dating’ for a few episodes.”
Hey, producers needed the drama!
Nick Lachey
Fresh off the breakup with Jessica Simpson in 2006, Nick Lachey rebounded with Kristin — but only for a short amount of time! On her Let’s Be Honest podcast in November 2024, she was around 18 or 19 when they began dating. Unfortunately, Kristin struggled to deal with all the media attention (and comparisons to the ex-wife) that came with being the new girlfriend of the 98 Degrees member! She said:
“This was a wild time in my life, because I was, overnight, on the cover of every tabloid. I had so many paparazzi following my every move, waiting outside of my house. He had just gotten a divorce from Jessica Simpson. So this was, like, the biggest thing in 2006. It was a wild ride.”
Although their romance was short-lived, she doesn’t seem to harbor ill will toward him (unlike toward some of her other exes)! She appeared on his Big Morning Buzz show in 2014, where they laughed over how they both had kids named Camden now. Great minds think alike, huh?
Nick Zano
Following her fling with Lachey, Kristin began dating another Nick that same year — What I Like About You star Nick Zano! And things were serious between the duo, even though they were only together for a short time! She ended up getting his initials tattooed on her wrist! Kristin may have thought it was a good idea at the time, but once they broke up in December 2007? Not so much! She reportedly got the ink removed. Lesson learned! Don’t get a tattoo tribute to your boyfriend of less than a year!
Miguel Medina
While Kristin was fake dating Brody on The Hills, she was actually involved with someone else on the show — a cameraman named Miguel Medina! During an episode of the reality show Very Cavallari, she revealed they secretly were involved during her time on the MTV series. The crew had no clue about Kristin and Miguel’s romance until the paparazzi got pictures of them at an airport in Canada. She said:
“We dated for a few months and nobody knew. And I was dating Brody on the show and like, meanwhile, Miguel was, like, filming it.”
Awkward! Kristin continued:
“Nobody knew because I’m a professional and we kept it under wraps. But, it was fun.”
The podcaster was annoyed their romance was exposed “a week before we wrapped the show,” but she ultimately has no regrets about anything:
“I dated a cameraman, yeah. Sure did.”
No shame!!
Jay Cutler
Kristin was only married once, and it was to Jay Cutler! After her relationship with Medina ended, she began dating the former Chicago Bears quarterback in 2010. They had a whirlwind romance, getting engaged after only eight months together. But according to her 2016 book Balancing in Heels, she broke up with him in July 2011 because “a few things needed to change.”
They didn’t stay away from each other, though. Kristin and Jay reconciled that same year and announced they were expecting their first child, Camden Jack Cutler, in January 2012. They went on to get married in June 2013 and have two more kids: Jaxon Wyatt and Saylor James.
Although Kristin and Jay seemed like a solid couple, we learned they were anything but! She announced they were divorcing after 10 years together in April 2020, citing both “irreconcilable differences” and “inappropriate marital conduct” in the divorce documents. A source claimed to Us Weekly they often would “accuse each other of cheating” during their “antagonistic” marriage. Yikes. And their post-divorce, co-parenting relationship hasn’t gotten any better, either! She really hates raising kids with Jay, calling him a “pathological liar” with “zero f**king consistency.” Damn.
It’s safe to say no one should ever, ever expect these two to get back together! Kristin and Jay are over for good!
Jeff Dye
Her first post-marriage rebound! Kristin sparked romance rumors with comedian Jeff Dye after they were spotted making out in Chicago in October 2020. The two got serious fast, with the two exchanging “I love yous” during an Instagram Live session in January of the following year. A month later, they posted matching love notes on their Instagram Stories for Valentine’s Day. However, their spark fizzled! They broke up in March 2021 after only five months together. A source for Entertainment Tonight said at the time:
“Kristin wasn’t ever looking for anything serious. She enjoyed Jeff’s company and he made her laugh, which she loved, but she never really saw anything long-term happening between them, especially with co-parenting being such a new thing for her right now. She’s focusing on the growth of her business and her kids. A serious relationship was never top of mind, at least for right now.”
In October 2023, Jeff wanted to get back together with Kristin. The 42-year-old actor even met up with her for a coffee date to broach the possibility of a second shot… but he got arrested for driving under the influence after fleeing the scene of a traffic collision right in front of her! So, any chance of a reconciliation went out the window! Granted, Jeff isn’t interested in her anymore! Not after Kristin then publicly blasted his DUI story to the whole world!
TBH, Jeff should’ve know Kristin is brutally honest about everything and anything! This was going to get out! Speaking of honesty…
Craig Conover
We need to discuss the bombshell Kristin dropped about the Southern Charm star in 2025! You may recall rumors that she was in a love triangle with Craig Conover and Austen Kroll circulated after her divorce from Jay in 2020. Kristin insisted she was only “friends” with the two guys at the time. However, she partially lied! She didn’t have a thing with Austen. They were truly pals! She did date Craig, though!
During an episode of Watch What Happens Live in June, Kristin confirmed she was with the Bravolebrity at the start of his relationship with Paige DeSorbo! He dated both of them at the same time! When Kristin “caught wind” Craig was also involved with the Summer House star, she “politely excused” herself:
“There was a picture of Craig and Paige in New York — I’ll never forget it — and it looked like they were sort of together. That was the first time anyone had seen them. That was the first time I had heard about it. I saw that picture, and I texted him and I said, ‘Hey, let’s just be friends.’”
And Kristin plans to remain just that, pals! Even though they are both single this year, she is not going down that path again!
Chase Rice
In September 2021, Kristin was seen packing on the PDA with country singer Chase Rice during a date at Losers Bar and Grill in Nashville — just days after her Jay stepped out with Jana Kramer. Remember those two together? Wild! But back to Kristin and Chase, an insider told People they were introduced through a mutual pal. They hit it off. The source shared that Kristin and Chase were together for “a little over a month” by the time their romance became public, and they were “having fun.”
Well, the fun ended quickly! By mid-October, Kristin revealed to her Instagram followers that there was “no one serious” in her life, and she was “not dating anyone.” So, that marked the end of the Chase romance!
Morgan Wallen
So remember when Kristin spilled that she had a romance with Morgan Wallen? Back in 2024, she opened up to Bunnie Xo that she and the country music star were f**k buddies in Nashville. The mom of three called him a “good guy” with a “big heart,” though she recognized he is “a player.” However, she didn’t care! She just wanted to have a good time between the sheets! And she did have a really good time with him! LOLz!
Kristin admitted he was “a great f**k buddy” and “good in bed.” Get it, girl! But beyond his bedroom abilities, she also thought Morgan was a “true gentleman” who went all out for the first date. He even took the time to meet her three children! Aww! They went to dinner in a “private room” at a restaurant and kissed in the rain when he took her home. It sounds so romantic!
Unfortunately, Kristin’s f**k buddy didn’t stick around. They didn’t talk for more than a year afterward — and she’s super bummed by how things ended! She explained on Bunnie’s Dumb Blonde podcast:
“He didn’t hurt my feelings. I’ll be honest with you. Morgan was the first guy in my entire f**king life that wasn’t, like, just completely enamored with me, and I was like, ‘What in the f**k is going on?’ It really threw me. … I love having the upper hand and I feel like with him I didn’t have the upper hand.”
LMFAO! At least she had fun!
Mark Estes
The award for Kristin’s hottest boyfriend, hands down, goes to 24-year-old Mark Estes! Sorry Chase and the others! In February 2024, she hard-launched her relationship with the much, much younger TikTok Star, best known for being a member of Montana Boyz, after they were caught on a vacation together in Mexico. They got serious FAST. Mark met her children, and the two even talked about having kids together.
However, their relationship fizzled after seven months. Why? While Kristin did not have a problem with their 13-year-age gap at first, it later became a big issue. She explained on her podcast:
“I broke up with Mark because I just know long term it’s not right. It’s not because of love lost or something bad happened, no one cheated, no one was mean. No one did anything. Those breakups are always the hardest, I think. I just know long term he needs to experience life. He’s young, I mean, he is. I started to feel the age a little bit just with life experience. I look back on when I was 24 and how much life has happened for me between then. Those are crucial years; those are formative years. This is when you find yourself, and he needs to be able to do that.”
Let’s be real. We all saw the breakup coming…
Nate Thompson
Nate was her last boyfriend… for now! In April 2025, Kristin revealed she started dating the retired professional hockey player late last year on the Let’s Be Honest podcast — but did so AFTER they already broke up! She explained they were “mostly long distance,” though Nate “came and stayed with [her] for New Year’s.” According to Kristin, this was “one of the deeper relationships” she ever had. And although they were not a couple for long, they “told each other f**king everything.” However, something was missing from the relationship! While Nate and Kristin had an emotional connection, they lacked physical chemistry:
“I need in the beginning to want to rip your f**king clothes off. I need compatibility and chemistry. I understand that what I’m searching for is rare. … I’m not gonna settle for anything less than exactly what I want.”
Because of that, their romance fizzled! They broke up, but she only had wonderful things to say about Nate! The same goes for him while he told his side of the story that same month! On his Energy Line podcast, the former athlete recalled they met “through Instagram” after the platform showed they “had a mutual friend.” He “reached out,” and they exchanged numbers. The next thing he knew, they were talking, and he was visiting Nashville to see her “a couple of times.” He continued:
“Obviously, we don’t live in the same city, so that dynamic changed things. I went there a couple times and saw her. I was with her for New Year’s. We told each other a lot of things in a short amount of time, and we were pretty open and honest about a lot of stuff.”
From his perspective, Nate felt they “had a connection in the short time that we talked or hung out” but he “wouldn’t have called her my girlfriend.” So, it sounds like this was more of a fling! In the end, he pointed out they “had a good time,” but “things didn’t work out.” Calling Kristin a “really good person” and “very genuine,” he added:
“She hustles. She does her thing, so I got a lot of respect for her and how she handles herself with everything she has to deal with being in the limelight.”
It’s a shame they didn’t last… But at least they ended amicably!
Bonus: Glen Powell
While they were not officially together, this feels important to include! Kristin’s best friend Justin Anderson revealed on the premiere episode of her new reality show Honestly Cavallari: The Headline Tour in June that she “went on a date with” Glen Powell! The hairstylist said:
“She recently went on a date with—she’s gonna be so mad at me actually – with Glen Powell! And I wanted it to happen so badly! Top Gun, bitch!”
Justin explained he and Kristin “were partying in Greece, and then Glen just came up.” According to her, the Scream Queens alum literally “ran into” her, and the sparks flew! Justin continued:
“And then you guys had a really fun night together.”
Get your heads out of the gutter! Ha! Kristin pointed out she “never f**ked him.” However, Justin revealed they “dry humped.” Oh! What a steamy night!
Honestly, we are also manifesting for a Glen and Kristin relationship! They would be a HOT couple! But if it’s not Mr. Top Gun, then who will she date next? Her celebrity crush, Kevin Costner? Who knows?! One thing we can trust Kristin to do, however, is keep us all on our toes when it comes to her love life!
Reactions, Perezcious readers? Let us know in the comments!
[Image via Access Hollywood/YouTube, MEGA/IPA/WENN, Mark Estes/Instagram]
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