The Shocking Truth About Kristin Cavallari And Glen Powell's 'Secret' Greek Hookup

The celebrity dating world is rarely dull, but the recent bombshell dropped by Kristin Cavallari in June 2025 has sent shockwaves through Hollywood. The reality star and entrepreneur revealed juicy details about a secret romantic encounter with A-list actor Glen Powell, a story that has been bubbling under the surface for some time. This exclusive, fresh information, unveiled on her new reality series, confirms a steamy, albeit brief, connection between the two stars during a trip to Greece, providing fans with an unexpected glimpse into Cavallari's private dating life.

The revelation has sparked intense curiosity, not just about the details of their rendezvous, but about the possibility of a future relationship between the Uncommon James founder and the *Top Gun: Maverick* heartthrob. While the details are salacious, Cavallari has been clear about her current focus, making the full context of their fling even more intriguing for fans following their respective careers and relationship timelines.

Full Profile: Kristin Cavallari and Glen Powell's Biography and Career Milestones

To fully appreciate the intersection of their lives, it is essential to understand the separate, high-profile careers of both Kristin Cavallari and Glen Powell. Their combined star power represents a significant cultural moment, blending reality TV royalty with blockbuster Hollywood success.

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Kristin Cavallari: Reality TV Icon to Business Mogul

• Full Name: Kristin Elizabeth Cavallari
• Born: January 5, 1987, in Denver, Colorado.
• Major Career Milestones:
  • 2004–2005: Rose to fame as a main cast member on the MTV reality series *Laguna Beach: The Real Orange County*.
  • 2009–2010: Continued her reality TV career on the spin-off series *The Hills*.
  • 2017: Launched her successful jewelry and lifestyle brand, Uncommon James.
  • 2018–2020: Starred in her own E! reality show, *Very Cavallari*, which documented her life as a businesswoman and her marriage to former NFL quarterback Jay Cutler.
  • 2020: Published her first cookbook, *True Comfort*, following her 2016 book, *Balancing in Heels*.
  • June 2025: Premiered her new reality series, *Honestly Cavallari: The Headline Tour*, where the Glen Powell hookup was revealed.
• Notable Entities: Stephen Colletti, Lauren Conrad, Audrina Patridge, Jay Cutler, Uncommon James, Laguna Beach High School, *The Hills*, *Very Cavallari*.

Glen Powell: Hollywood's New Leading Man

• Full Name: Glen Thomas Powell Jr.
• Born: October 21, 1988, in Austin, Texas.
• Major Career Milestones:
  • 2003: Began his career with a small role in *Spy Kids 3-D: Game Over*.
  • 2015–2016: Gained recognition for his role as Chad Radwell in the Fox horror-comedy series *Scream Queens*.
  • 2016: Received critical acclaim for his performance as astronaut John Glenn in the biographical drama *Hidden Figures*.
  • 2022: Achieved global stardom as Lt. Jake "Hangman" Seresin in the critically and commercially successful film *Top Gun: Maverick*.
  • 2023: Starred as Ben in the romantic comedy *Anyone But You* alongside Sydney Sweeney, which became a box-office hit.
  • 2024: Starred in the disaster film *Twisters*.
• Notable Entities: Tom Cruise, Sydney Sweeney, Austin, Texas, Richard Linklater, *The Dark Knight Rises*, *The Expendables 3*, John Glenn, *Scream Queens*, *Twisters*.

The Juicy Details: What Really Happened Between Cavallari and Powell in Greece?

The highly-anticipated premiere of *Honestly Cavallari: The Headline Tour* in June 2025 delivered on its promise of headline-worthy revelations. The bombshell was dropped not by Cavallari herself, but by her long-time best friend and celebrity hair stylist, Justin Anderson.

During a candid moment on the show, Anderson unexpectedly revealed to the live audience that Cavallari "recently went on a date" with the *Top Gun* star. This prompted Cavallari to reluctantly spill the full story about her romantic run-in with Glen Powell while they were both vacationing in Greece.

The "Dry-Humping" Confession

The most shocking detail of the story was Cavallari's own description of the encounter. She confirmed that while they did not have full intercourse, they did engage in a steamy session, which she explicitly referred to as "dry-humping." This candid description immediately went viral, capturing the attention of fans and media outlets alike, who were fascinated by the casual yet intimate nature of the celebrity hookup.

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The encounter, which occurred while both stars were out partying in Greece, was a fleeting, passionate moment. The fact that the story was kept a secret for so long, only to be revealed on a live show by her closest friend, adds a layer of drama and authenticity that has become a hallmark of Cavallari's reality television career.

Current Status and Future Prospects: Are They Dating Now?

Despite the undeniable chemistry and the steamy nature of their Greek rendezvous, Kristin Cavallari has been very clear about the current status of her relationship with Glen Powell—and her overall dating life—as of late 2025. The answer to whether they are an item is a definitive "No."

Focus on Family Over Flings

Cavallari, who finalized her divorce from Jay Cutler in 2022, has repeatedly stated that she is not actively seeking a committed relationship at this time. Her primary focus remains on her three children and her burgeoning business empire, Uncommon James.

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She has explained that she is enjoying her single life and the freedom it affords her, a sentiment she reiterated shortly after the Powell revelation. She is not interested in dating Glen, or any other celebrity, at the moment. In a refreshingly honest statement, she noted that she plans to wait until her children are older before seriously pursuing a new partner.

Glen Powell's Relationship Status

Glen Powell's dating life has also been a subject of intense media scrutiny, particularly following the massive success of *Anyone But You* and the viral chemistry he shared with co-star Sydney Sweeney. While he has been linked to several high-profile women, his current relationship status is often kept private, adding to the intrigue surrounding the Cavallari hookup. The revelation serves as a reminder that both stars are currently unattached and enjoying their freedom, which occasionally leads to these kinds of spontaneous, European adventures.

The Impact of the Revelation on Celebrity Dating Culture

The story of Kristin Cavallari and Glen Powell is more than just a celebrity gossip item; it reflects a broader shift in how public figures discuss their private lives. Cavallari's willingness to be so candid about a casual, non-committal sexual encounter, even using the term "dry-humping," is a testament to the new era of reality TV and podcast culture, where oversharing is often rewarded with higher engagement and "topical authority."

By bringing the story to light on *Honestly Cavallari: The Headline Tour*, she controls the narrative, turning a private moment into a key storyline for her new show. This strategic move ensures the conversation stays centered on her, driving buzz for her brand and her projects. While a long-term romance with the Austin-born actor may not be in the cards, the brief, steamy chapter in Greece will undoubtedly remain a fascinating footnote in the dating histories of both Kristin Cavallari and Glen Powell.

The public is left to wonder if their paths will ever cross again, perhaps leading to a second, less-secretive rendezvous. For now, however, both stars are firmly focused on their professional pursuits, leaving the dry-humping in Greece as a fun, memorable headline for the summer of 2025.