The Glen Powell and Kristin Cavallari hookup revelation captivated fans during a live Atlanta show on Kristin’s Let’s Be Honest podcast tour, where her best friend, Justin Anderson, surprised the audience with details of the encounter. The disclosure on E!’s Honestly Cavallari: The Headline Tour quickly became a lightning rod for public fascination, due to both celebrities’ high profiles and Cavallari’s recent openness about her personal life after her divorce from Jay Cutler.
Unexpected Secrets Revealed During Podcast Tour
Taking the stage in Atlanta, Kristin Cavallari fielded questions from her audience, many eager to learn about her dating life since the end of her marriage to Jay Cutler. After a question on her romantic updates, she described focusing primarily on her children, Camden, Jaxon, and Saylor, following her 2022 split. In her words,
“It’s been a lot with my kids in the last year, I now have them a lot more than I did, so dating hasn’t been the priority. In nine years when my kids are off at college, I’m gonna be all over the world with all the guys doing all the things.”
—Kristin Cavallari, Reality Star
However, the evening swerved dramatically when Justin Anderson, her close confidant and celebrity hairstylist, took the microphone. Amid cheers from the crowd, he revealed that Cavallari had a recent, unexpected date with Glen Powell, an acclaimed actor known for his role in “Top Gun.” As Anderson 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, b—h!”
—Justin Anderson, Celebrity Hairstylist.
Kristin, visibly embarrassed and caught off guard, responded simply, exclaiming Justin’s name in protest as the crowd absorbed the news.
The Night in Greece: More Details Surface
A flashback moment detailed the context of the connection. Justin recounted,
“We were partying in Greece, and then Glen just came up,”
—Justin Anderson, Celebrity Hairstylist. Kristin interjected, clarifying she had not planned the meeting: “Literally ran into me.” Justin elaborated further,
“And then you guys had a really fun night together.”
—Justin Anderson, Celebrity Hairstylist.
Kristin was candid with boundaries, stating,
“I never f–ked him. I’m just putting that out there.”
—Kristin Cavallari, Reality Star. Justin, continuing the playful recounting, added, “You guys dry humped though,” to which Kristin confirmed with a laugh, “Yeah, we did.” The exchange, playful and revealing, underscored the underlying tension and camaraderie between the longtime friends.
Back at the live podcast, Kristin felt the need to make her stance clear to her fans and future media coverage:
“Okay, I have to go on record, when this comes out, I had nothing to f–king do with it!”
—Kristin Cavallari, Reality Star.
Kristin Cavallari’s Relationship Timeline: Revisiting Her Notable Romances
The Glen Powell revelation prompted a broader look at Kristin’s romantic history, marked by numerous high-profile relationships and often public breakups, each marked by intense public scrutiny. From her early days on reality TV to connections with actors, athletes, and musicians, Cavallari’s private life has long been a topic of media fascination.
Stephen Colletti: The First Love Broadcast Nationwide
Kristin’s relationship with Stephen Colletti, castmate on Laguna Beach, was one of her earliest and most significant. Their romance, beginning before the MTV cameras rolled, turned into a televised saga that introduced viewers to the complexities of teenage love. Reflecting on that relationship, Kristin wrote,
“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. 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.”
—Kristin Cavallari, from Balancing in Heels.
Though their romance did not last, they sustained a strong friendship, and Cavallari mentioned his willingness to revisit old ties for appearances on later projects.
Talan Torriero: Off-Camera Hookups and Behind-the-Scenes Drama
Laguna Beach’s Talan Torriero was another key figure during those turbulent years. Recalling the complexity of relationships off-camera, he remarked,
“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.”
—Talan Torriero, Laguna Beach Cast Member.
He further explained,
“I will say that before the show aired, there were already relationships happening, or hookups, if you will.”
—Talan Torriero, Laguna Beach Cast Member. Their on-and-off romance underscored the high school experience under the lens of reality television.
Matt Leinart: Short-Lived Connection with the College Quarterback
After her fallout with Stephen, Kristin’s brief romance with USC quarterback Matt Leinart was referenced in the opening of Laguna Beach’s second season. Their relationship drew whispers and speculation, and despite a fleeting reunion in 2008, they drifted apart without rekindling a deeper connection.
Brody Jenner: From Reality TV Romance to Real-Life Couple
Brody Jenner’s involvement with Kristin began after her time on Laguna Beach and later took on a scripted form on The Hills. As Kristin shared,
“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.”
—Kristin Cavallari, Reality Star, on Bethenny.
The pair maintained an amicable split, with Kristin reflecting,
“It’s just hard right now because I am working all the time.”
—Kristin Cavallari, Reality Star. This mutual respect allowed them to remain friends despite the pressures of constant filming and public attention.
Nick Lachey: Rumor-Fueled Friendship After a High-Profile Divorce
Kristin and Nick Lachey were at the center of romance rumors in 2006, soon after his divorce from Jessica Simpson. Kristin addressed the talk directly:
“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.”
—Kristin Cavallari, Reality Star.
However, the period marked a new level of tabloid fever for Kristin, who described the relentless attention as,
“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.”
—Kristin Cavallari, Reality Star. Lachey’s own notoriety contributed to the media’s obsession with their interaction.
“This was, like, the biggest thing in 2006,”
she later remarked—Kristin Cavallari, Reality Star.
Nick Zano: The Actor Romance That Led to Permanent Ink
Kritin’s relationship with actor Nick Zano quickly turned serious, leading her to commemorate it with a tattoo of his initials. Their love faded by December 2007, and Cavallari soon removed the tattoo, a symbolic end to that chapter.
Miguel Medina: A Hidden Relationship During ‘The Hills’
While filming The Hills, Kristin kept a secret romance with MTV cameraman Miguel Medina, hidden even from close castmates like Heidi Montag and Audrina Patridge. She later disclosed,
“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.”
—Kristin Cavallari, Reality Star.
Kristin recounted the moment the secret unraveled:
“Paparazzi got us at the airport a week before we wrapped the show. That’s how we got caught.”
—Kristin Cavallari, Reality Star.
Jay Cutler: Marriage, Parenthood, and Moving On
Kristin’s next highly publicized relationship was with Jay Cutler, famed quarterback for the Chicago Bears. The couple’s whirlwind romance included a brief engagement break, with Kristin reflecting in her book that
“a few things needed to change.”
Together, they welcomed Camden, Jaxon, and Saylor, marrying in 2013. By April 2020, Cavallari and Cutler announced a divorce, leading to significant changes in her sense of self.
“The scariest thing that I’ve ever done is get a divorce. 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.”
—Kristin Cavallari, Reality Star, to The School of Greatness Podcast.
Jeff Dye: Post-Divorce Fling with the Comedian
Following her split from Cutler, Kristin briefly dated comedian Jeff Dye. Despite public displays of affection, a source close to the reality star confirmed,
“It was never that serious to begin with.”
—Unnamed Insider, to E! News. Dye, in turn, shaped the narrative with a personal reflection,
“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.”
—Jeff Dye, Comedian.
Chase Rice: A Fun but Fleeting Connection with the Country Star
In August 2021, Kristin was linked to country musician Chase Rice. At the time, an E! News insider shared,
“At the moment, it’s still casual. It’s new. She’s been to one of his shows already and they’re having fun.”
—Unnamed Insider to E! News. Their time together was brief, and soon thereafter, Kristin publicly stated she had resumed single life.
Morgan Wallen: Honesty About a Dalliance with the Country Singer
By late 2024, a new episode of the Dumb Blonde podcast revealed Kristin’s connection with Morgan Wallen. She described the country star in glowing yet blunt terms, mentioning his prowess and gentleman-like behavior.
“The first date that we went on, he was a true gentleman, and he was like, ‘I’ll pick you up, I’ll pick the place,’ like, just f–king handled business.”
—Kristin Cavallari, Reality Star. The charming details continued,
“He kissed me in the rain, and it was the sweetest thing.”
—Kristin Cavallari, Reality Star.
Mark Estes: TikTok Romance Impacted by Age Gap
Montana Boyz’s Mark Estes, whom Kristin called “the best boyfriend” she’s had, represented a significant relationship, but ultimately a challenging age difference led to its end. She explained the heartbreak and logic behind her decision:
“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.”
—Kristin Cavallari, Reality Star.
She further explained her perspective:
“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.”
—Kristin Cavallari, Reality Star.
Nate Thompson: A Deep Connection with the Retired NHL Player
As recent as April 2025, Kristin confirmed on her podcast that she had dated retired NHL player Nate Thompson. About the relationship, she shared,
“He’s someone who has done a lot of work on himself, and we really connected on such a deep level,”
and called it,
“one of the deeper relationships I’ve had.”
—Kristin Cavallari, Reality Star.
Nate Thompson mirrored her sentiments and gave his own take on their relationship:
“We had a good time. Life is gonna life and it just didn’t work out.”
—Nate Thompson, Retired NHL Player.
The Public Fascination: Why Kristin Cavallari’s Relationships Remain Under the Spotlight
The Glen Powell and Kristin Cavallari hookup revelation has added a sensational new chapter to Cavallari’s already extensive romantic history, drawing sharp attention from her fans and media alike. Whether relating to high school boyfriends like Stephen Colletti and Talan Torriero, musicians such as Morgan Wallen and Chase Rice, actors including Glen Powell and Nick Zano, or athletes like Jay Cutler and Nate Thompson, Cavallari’s love life often intertwines with celebrities, intensifying public intrigue.
Through each relationship, and especially after candid admissions during live events and podcasts, Cavallari’s journey highlights both the rewards and the scrutiny that come with living so much of one’s personal life in the public eye. As Honestly Cavallari: The Headline Tour continues and fans eagerly anticipate more revelations, the impact of these disclosures shows no sign of fading, ensuring that the Glen Powell and Kristin Cavallari hookup revelation will remain a hot topic among entertainment watchers and reality television enthusiasts alike.
