Kristin Cavallari Pissed After Awkward Reunion With First Boyfriend
Kristin Cavallari's blast from the past did not turn out like she had hoped.
The Laguna Beach alum reunited with her very first boyfriend during the June 11 episode of E!'s Honestly Cavallari: The Headline Tour—and it did not go well.
"I'm going to be pulling up Johnny, my very first boyfriend from Chicago," Kristin explained during a confessional before one of her live Let's Be Honest podcast shows in Illinois. "I've talked about him a couple times on the podcast. We were as in love as you could be at the tender age of 13 and 14."
The 38-year-old noted Johnny was "nervous" about being a guest since he isn't in the public eye and they hadn't seen each other in 15 years.
"For people who don't do this, it's f--king nerve-wracking," Kristin added. "So, I even appreciate him getting up."
Plus, the reality star thought it would be fun to catch up with the man she lost her virginity to.
"Johnny was actually coming to the Chicago show anyway," she elaborated in a confessional. "I was like, 'Wait a minute, this could be really fun.' We all know how it is to get over your first love, it's very difficult. And I do wonder if I've sort of, like, changed the narrative in my mind all these years. To have his perspective is gonna be awesome."
But when Johnny was finally pulled up on stage, the encounter was more combative than Kristin expected.
After Kristin told the audience of their relationship, "I would wake up in the morning and I would have poems on my window," Johnny interrupted with a different recollection. "You'd wake up next to me. That's the podcast version," he retorted. "To be clear, you would actually greet me in outfits just like this. I saw you come out in this and it's hard."
The awkward comment threw Kristin off, but the worst was still to come. Johnny then accused Kristin of having a wandering eye.
"Before you left, you were sampling Barrington, [Ill.]," he added. "You broke my heart actually because you hooked up with my best friend [Tommy]."
A shocked Kristin denied the claim. "I don't even remember Tommy," she shot back. "I hooked up with Tommy?!"
Needless to say, Kristin wasn't happy with Johnny trying to make her look like the bad one in the relationship.
"Johnny is a massive letdown," the mother of three lamented in a confessional. "It honestly breaks my heart because for all of these years I have held my relationship with Johnny in this high regard. And then he got up on stage and he was a completely different person."
"He was the only person I gave the questions to beforehand because obviously he doesn't do this stuff.," she continued. "He knew exactly what I was going to say, so, to me, it just feels premeditated, like he wanted to come out there and tear me down. These memories that I've had with Johnny all of these years are now just completely ruined. "
The next day, Kristin was still fuming over the uncomfortable interaction.
"You wanna trash me in front of my f--king audience?" she ranted to BFF Justin Anderson. "It's f--ked up! It's really f--ked up. I hate Johnny."
A calmer Kristin then revealed the surprising text she received from Johnny after the show.
"'You were amazing last night,'" she read to Justin. "'Thanks for such a fun escape from reality, definitely needed that. You're gonna absolutely crush the rest of your tour. No doubt about it.'"
And after her former Laguna Beach costar and former boyfriend Talan Torriero pulled a similar stunt during another live show, Kristin was done with the men of her past.
"I actually don't even care about looking like an idiot in front of the audience," she admitted to Justin. "This is a much bigger thing for me. It's the theme of my whole life. With Talan, it's like, 'Okay, it's expected.' Then Johnny, it was like, 'Oh my god!' Like, no guy has ever taken accountability in my life, ever."
Now, Kristin no longer entertains that type of behavior from men.
"I've allowed these men into my life and I can see it a mile away now," she reflected. "It's a nice reminder of how far I've come."
See Kristin's tour continue when Honestly Cavallari: The Headline Tour airs Wednesday at 10 p.m. on E!.
In the meantime, keep reading to look back at Kristin's star-studded dating history.
You never forget your first love...especially when MTV's cameras are around to document every high and low in the dramatic relationship. Viewers got to see Kristin Cavallari and Stephen Colletti's love story play out on Laguna Beach for two seasons, with the pair, who began dating the year before the show began filming, and Lauren Conrad delivering one of TV's great love triangles.
"We loved hard and fought hard. My relationship with Stephen went from our own high school romance to the fodder of a hugely successful television show," Kristin wrote in her 2016 book, Balancing in Heels. "Stephen was the most important thing in my life, and there was nothing I cared about more. I hated fighting with him on camera because it felt like I was airing all our dirty laundry."
While their romance couldn't make it out of high school intact, the two have remained friends, with Kristin once telling E! News he was down to make an appearance on Very Cavallari.
Speaking to E! News in 2022, Laguna Beach's resident lothario Talan Torriero admitted that while everyone was focused on the LC-Stephen-KCav triangle, "The reality is there were so many other storylines going on behind the scenes. Not even with myself, but with Kristin or even with Lauren. Lauren had other boyfriends while she was high school, some really cool dudes that I know that never wanted to be on the show or were on the show."
As for his hot-and-cold romance with Kristin, "I will say that before the show aired, there were already relationships happening, or hookups, if you will," Talan clarified. "I didn't hang out with Lauren until later, like in my second season or something. Kristin, junior and senior year, on and off."
In the season two premiere of Laguna, Stephen is devastated when he learns Kristin has moved on after he left for school, dating "Matt, this guy at USC."
This guy at USC would turn out to be Matt Leinart, USC's star quarterback who would go on to play in the NFL. Matt never ended up appearing on the MTV hit and his romance with Kristin was short-lived.
The pair briefly sparked reconciliation rumors when they were spotted together in Vegas in 2008, but Kristin and Matt didn't officially huddle up again.
While they would later fake a romance for The Hills' later seasons, Kristin and Brody Jenner did date years prior shortly after her tenure on Laguna Beach ended when they were introduced by Talan.
"I dated Brody when I was 18, right after Laguna Beach, actually, and that's it," she spilled on Bethenny in 2012. " And then on the show, on The Hills, they had us 'dating' for a few episodes."
Though they were on and off for almost a year, the pair were officially dunzo in 2006. "It's just hard right now because I am working all the time," she told People. "We're still good friends though."
Kristin and 98 Degrees singer Nick Lachey sparked romance rumors when they were spotted together in early 2006, a year after his high-profile split from then-wife Jessica Simpson.
Kristin shot down the rumors at the time, telling People, "There's nothing to talk about, there's nothing going on. He's a nice guy, but I'd have to say we're just friends."
Though, as she later admitted, she was simply trying to escape the sudden, glaringly hot attention.
"This was a wild time in my life, because I was, overnight, on the cover of every tabloid," she shared on a November 2024 episode of her Let’s Be Honest podcast. "I had so many paparazzi following my every move, waiting outside of my house."
Fresh off the end of his Newlyweds era with Jessica, "This was, like, the biggest thing in 2006," she added. "It was a wild ride."
Shortly after her romance with Brody fizzled out, Kristin began dating actor Nick Zano, best known for the WB sitcom What I Like About You.
Things were pretty serious between the two, with Kristin even getting his initials tattooed on her wrist.
But when the pair called it quits in December 2007, Kristin had the tattoo removed.
While Kristin was faking romances on-screen with Brody and Justin Bobby Brescia, she was actually secretly dating someone behind-the-scenes during her time on The Hills.
In 2010, Kristin was dating MTV camerman Miguel Medina, managing to keep their relationship a secret even from her co-stars Heidi Montag and Audrina Patridge.
"We dated for a few months and nobody knew," she revealed to her former co-stars in an episode of Very Cavallari. "And I was dating Brody on the show and like, meanwhile, Miguel was, like, filming it."
She then went on to say their relationship was exposed toward the end of their time working together because "paparazzi got us at the airport a week before we wrapped the show. That's how we got caught."
Shortly after she wrapped her romance with Miguel, Kristin caught the eye of then-Chicago Bears quarterback Jay Cutler. While the athlete made a big play a year into their romance, proposing in 2011, Kristin ended the relationship a few months later, sharing in her book Balancing In Heels, that "a few things needed to change."
Having properly diagrammed the Xs and Os, the pair welcomed son Camden in August 2012, married in June 2013 and went on to add to their squad with son Jaxon in May 2014 and daughter Saylor in November 2015. Though they seemed to be a solid team, Kristin has come clean about their locker room dynamic since they announced the end of their marriage in April 2020.
"The scariest thing that I've ever done is get a divorce," she said on The School of Greatness podcast in 2022. "But it's been the best thing that I've ever done and that has really jumpstarted my journey on self-love and figuring out who I am now."
Following her divorce from Jay, Kristin tried to find the funny with Los Angeles-based comedian Jeff Dye. But despite exchanging those three little words during a January 2021 Instagram Live, "It was never that serious to begin with," an insider told E! News that March, announcing their split. "She was having fun."
At least one of them was. "We didn't even really date," the comic recounted in November 2024. "I'm gonna say that publicly. She made me think that I might have a chance with her. She treated me like a little puppy."
By August 2021, Kristin found a new duet partner in country singer Chase Rice. "At the moment, it's still casual. It's new," the insider told E! News at the time. "She's been to one of his shows already and they're having fun."
But weeks later, it appeared the Nashville residents were enjoying solo acts, with Kristin sharing on Instagram, "I'm currently not dating anyone."
While the rest of Kristin's love life is still unwritten, she came clean about one chapter in late 2024—her dalliance with country singer Morgan Wallen.
"He's a great f--k buddy," Kristin said on a December episode of Bunnie XO's Dumb Blonde podcast. "He was good in bed."
And he's got some smooth moves out of the bedroom as well.
"The first date that we went on, he was a true gentleman," she added, "and he was like, 'I'll pick you up, I'll pick the place,' like, just f--king handled business." And after scoring a private room after the venue they visited, "He kissed me in the rain," she revealed, "and it was the sweetest thing."
Though Kristin dubbed Montana Boyz TikTok star Mark Estes “the best boyfriend" she's ever had, she had to be honest about how much she struggled with their 13-year age gap.
“I broke up with Mark because I just know long term it’s not right,” she shared on her podcast in October 2024, shortly after announcing the end of their seven-month romance. “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.”
Ultimately, though, “I just know long term he needs to experience life,” she explained. “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.”
Months after teasing that she had been “dating” a retired athlete, Kristin confirmed she was referring to the former NHL player on her podcast in April 2025.
“He's someone who has done a lot of work on himself, and we really connected on such a deep level,” she said, describing the romance as “one of the deeper relationships I've had.”
Later that day, Nate addressed the relationship on his own podcast, Energy Line, echoing Kristin’s high praise.
“She’s a cool person,” he gushed. “We had a good time. Life is gonna life and it just didn’t work out.”
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