As a die-hard admirer of both Kristin Cavallari and Glen Powell, I can’t help but share the thrill when I learned about their recent, seemingly serendipitous meeting. Now, while they didn’t actually lock lips, let’s just say there was a spark in the air that had fans like me dancing with joy!
On the debut of TopMob’s newest show, “Honestly Cavallari: The Headline Tour,” the reality star’s close friend, Justin Anderson, revealed details about her recent high-profile romance with a celebrity.
At her “Let’s Be Honest” podcast event in Atlanta, Kristin addressed queries from her bustling audience, one of whom inquired about the current state of her romantic relationships, given her 2022 divorce from ex-husband Jay Cutler. Together, they have three children: Camden (12), Jaxon (10), and Saylor (9).
The former star of “Very Cavallari” confessed during the June 4 episode that it’s been quite busy taking care of her kids in the past year. She now spends more time with them than before, which has made dating less important for her. However, she joked that when her children leave for college in nine years, she plans to travel extensively and have numerous adventures with various partners around the world.
It was then that Justin exposed his close friend by disclosing her short-lived affair with a specific film actor.
The popular hairstylist revealed that she had gone on a date with Glen Powell, causing her to feel a bit guilty. As the audience erupted in applause, she excitedly exclaimed, “It’s ‘Top Gun’ guy! Oh, I’ve been wishing for this!
And extremely embarrassed Kristin simply responded by shouting, “Justin!”
In a flashback, the pair went into deeper detail about the past hookup.
Justin described how we were having a great time in Greece, and suddenly Glen appeared. But as he put it, Glen didn’t just show up – he literally ran into Kristin,” she added.
Justin continued, “And then you guys had a really fun night together.”
However, the Laguna Beach alum clarified, “I never f–ked him. I’m just putting that out there.”
Afterward, Justin casually mentioned another intriguing point: “We simulated dry humping, didn’t we?” To this, Kristin chuckled and agreed, “Absolutely, we did!
At the live event, Kristin assured her fans that the incident was not meant to be disclosed.
The person stated, ‘I must make a formal statement.’ Addressing her listeners, she continued, ‘Once this matter is released, I have no connection whatsoever to it!’
Keep reading for a look back at the rest of Kristin’s star-studded dating history.
Don’t forget to catch more stunning revelations from Kristin on “Honestly Cavallari.” It airs every Wednesday at 10 p.m., only on TopMob.
The special bond you share with your first love is hard to forget, especially when a camera crew from MTV is present to capture every up and down in your dramatic relationship. During the broadcast, fans were able to witness Kristin Cavallari and Stephen Colletti’s romantic journey unfold on Laguna Beach for two seasons. The trio, which included Lauren Conrad, created one of television’s most memorable love triangles as they navigated their relationships while being filmed.
Kristin expressed in her 2016 book, Balancing in Heels, that she deeply cherished and battled fiercely in her relationship with Stephen. This bond, which originated from our shared high school romance, became the basis for a wildly popular television series. For Kristin, Stephen was the central focus of her life, and there was nothing she valued more. She detested arguing with him on camera because it seemed like they were exposing all their personal conflicts.
As their romantic connection didn’t survive beyond high school, we’ve managed to stay friends. In fact, I shared with TopMob News that I wouldn’t mind making a guest appearance on Very Cavallari.
In an interview with TopMob News in 2022, I, Talan Torriero, a resident of Laguna Beach, shared some untold truths about our beloved series. Contrary to popular belief, the LC-Stephen-KCav triangle wasn’t the only storyline worth noting. There were numerous other intriguing plotlines happening off-screen, even with characters like Kristin and Lauren. In fact, while she was in high school, Lauren had other boyfriends who were quite impressive individuals, some of whom chose not to be part of the show or were briefly featured on it.
Regarding his turbulent relationship with Kristin, Talan explained that there were connections, or encounters if you prefer, prior to the show’s debut. “I didn’t start spending time with Lauren until later, in my second season, for instance,” he said. “Kristin and I had our ups and downs during our junior and senior years.
In the opening episode of the second season of Laguna, I found myself reeling as I discovered that Kristin had moved forward in my absence, finding companionship with a fellow student named Matt from USC.
This is a more personalized and conversational way to express the original statement while maintaining its essence.
It was eventually this individual from USC who became well-known as Matt Leinart, their star quarterback who later played professional football in the NFL. However, he didn’t make it onto the MTV show and his relationship with Kristin didn’t last long.
In 2008, a brief flurry of speculation about reconciliation arose when Kristin and Matt were seen together in Las Vegas, but they never formally reunited officially.
In the subsequent seasons of “The Hills,” Kristin and Brody Jenner portrayed a relationship that was not genuine, but they had actually dated earlier, around the time when Kristin’s tenure on “Laguna Beach” concluded. They got to know each other when introduced by Talan.
She confessed during an interview on Bethenny in 2012 that she went out with Brody when she was 18, following the show Laguna Beach. However, their relationship was only portrayed as ongoing for several episodes on The Hills.
In 2006, they officially ended their relationship, which had been intermittent for nearly a year. She explained to People magazine that it was difficult due to her busy work schedule, but they remain close friends.
In the beginning of 2006, Kristin and Nick Lachey, who was a member of the band 98 Degrees, fueled romance speculation as they were seen together. This encounter took place a year after his well-known separation from Jessica Simpson, his then-spouse.
At that point, Kristin dismissed the gossips, stating to People magazine, “There’s simply nothing to discuss, no ongoing events. He’s a great individual, but I must emphasize that we’re merely friends.
Initially, she tried to avoid the unexpected, intensely bright focus that was on her. Later on, she confessed this was just an attempt to evade the spotlight.
She stated that this period in her life was incredibly chaotic, as she suddenly found herself on the front page of all tabloids. During this time, she experienced an overwhelming number of photographers constantly tracking her actions, lingering outside her home. This was mentioned during a November 2024 episode of her “Let’s Be Honest” podcast.
After wrapping up his “Newlyweds” chapter with Jessica, she remarked, “This was undeniably the most notable event in 2006.” She described it as an exhilarating journey.
Not long after her relationship with Brody ended, Kristin started seeing actor Nick Zano, who is well-known for his role in the WB sitcom “What I Love About You.
The relationship between them was quite intense, as Kristin went as far as getting their initials inked on her wrist.
But when the pair called it quits in December 2007, Kristin had the tattoo removed.
As Kristin was portraying romantic relationships with Brody and Justin Bobby Brescia in the show, she was discreetly seeing someone off-camera during her tenure on The Hills.
Back in 2010, Kristin was in a secret relationship with MTV camerman Miguel Medina. Even her fellow cast members Heidi Montag and Audrina Patridge were unaware of this romantic connection.
In an episode of “Very Cavallari,” I shared a secret: for several months, I had been seeing someone special away from the public eye. While portraying my relationship with Brody on the show, I was actually dating Miguel simultaneously as he filmed our interactions.
Later, she explained that due to the paparazzi capturing them at the airport a week prior to wrapping up the show, their relationship became public knowledge. Essentially, they were discovered.
Following her split with Miguel, Kristin attracted the attention of Jay Cutler, who was then the quarterback for the Chicago Bears. After just one year together, Jay made a significant move by proposing in 2011. However, Kristin called off the relationship a few months later, explaining in her book “Balancing In Heels” that “certain aspects required adjustment.
After carefully setting up the Xs and Os, the couple welcomed their son Camden into the world in August 2012, got married in June 2013, and expanded their family with son Jaxon in May 2014 and daughter Saylor in November 2015. Despite appearing to be a strong team, Kristin has recently opened up about the inner workings of their relationship since they announced their separation in April 2020.
She shared on the “School of Greatness” podcast in 2022 that the most terrifying experience she’s had was going through a divorce. However, she also admitted that it was the best decision she ever made, as it set her on a path to self-discovery and learning more about who she is now, focusing on self-love.
After her divorce from Jay, Kristin explored comedy with comedian Jeff Dye based in Los Angeles. However, even though they expressed mutual affection during a January 2021 Instagram Live (“It was never that serious to begin with”), an informant shared with TopMob News in March that their relationship had ended. The source indicated that Kristin was simply enjoying herself.
In November 2024, the comedian stated that they didn’t truly date. However, he admitted openly that she led him to believe there could be potential between them. He compared her behavior towards him as if she was treating a small puppy.
By August 2021, Kristin had discovered a fresh duet collaborator in country artist Chase Rice. An informant shared with TopMob News that it was all quite casual, brand new at the time. “She’s even attended one of his concerts already and they’re enjoying themselves,” the source added.
However, as time passed (approximately several weeks), it became clear that Nashville locals had been indulging in solitary performances. Kristin herself announced on Instagram that she was currently single, stating, “I don’t have a partner at the moment.
Although details about most of Kristin’s romantic history remain unknown, it was in late 2024 that she admitted to a past relationship with the country musician Morgan Wallen – a chapter in her love story.
In one of Bunnie XO’s Dumb Blonde podcast episodes from December, Kristin stated, “He was an excellent bed partner.
And he’s got some smooth moves out of the bedroom as well.
On our initial date, he truly exhibited chivalrous behavior, she remarked. Furthermore, he said something like, ‘I’ll come to get you, I’ll choose the location,’ effectively taking care of things smoothly. And following our visit to that place, ‘He kissed me in the rain,’ she disclosed, which was incredibly sweet and romantic.
Despite Kristin labeling Mark Estes as the best boyfriend she’s ever known on TikTok as Montana Boyz, she openly admitted that the significant 13-year age difference between them posed challenges for her.
In October 2024, she revealed on her podcast that she ended things with Mark as she felt in the long run it wasn’t suitable. It wasn’t due to a lack of love or any negative event; there was no cheating, no harsh words, nothing like that. Breakups without obvious reasons can be particularly challenging, I believe.
Essentially, she pointed out, “He must live and learn over the long term, because he’s still young and these years are significant. They shape who we become. At his age, 24, I had barely scratched the surface of my life experiences. Those years are pivotal; they help us discover ourselves. It’s important for him to do the same.
In April 2025, Kristin admitted on her podcast that when she hinted about dating a retired athlete back then, she was indeed talking about the ex-NHL player.
She explained that he’s put a great deal of effort into personal growth, and their bond runs incredibly deep. Regarding their relationship, she described it as one of the most profound connections she’s experienced.
In the evening, Nate spoke about their relationship during his podcast, _Energy Line_, mirroring Kristin’s heartfelt compliments.
He enthusiastically agreed, “She’s really great company,” he said. “We enjoyed each other’s company. Sometimes, life takes unexpected turns and unfortunately, things didn’t pan out between us.
Don’t miss the premiere of Honestly Cavallari: The Headline Tour Wednesday, June 4, at 10 p.m. on TopMob.
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2025-06-05 06:17