Kristin Cavallari’s Dating History: From Reality TV Romances to Post-Divorce Love
Stephen Colletti
During her teenage years on MTV’s Laguna Beach, Cavallari shared a tumultuous romance with co-star Stephen Colletti that captivated viewers. Following the show’s conclusion, their relationship dissolved after appearing together for two seasons.
The former flames maintained a friendship over the years, collaborating in 2022 to create Back to the Beach with Kristin and Stephen – a podcast revisiting their MTV days. During a July 2022 recording, they disclosed their off-camera relationship had begun a year prior to filming.
Talan Torriero
At age 18, Cavallari embarked on a brief romance with NFL athlete Matt Leinart during her final high school semester. Despite their short-lived connection, the reality star praised her “first quarterback” during a January 2023 podcast episode, describing him as exceptionally kind-hearted.
Brody Jenner
The television personalities rekindled their early-2000s connection during The Hills era, sparking speculation about renewed romantic possibilities. Jenner later commended Cavallari’s vibrant personality during a 2021 interview about their The Hills: New Beginnings reunion.
“She brings incredible energy to every scene,” Jenner remarked to PeopleTV. “Her presence is always electrifying.”
Justin “Justin Bobby” Brescia
While Brescia’s complicated relationship with Audrina Patridge dominated The Hills storylines, Patridge later suggested in her memoir that Brescia developed authentic feelings for Cavallari despite their staged interactions. Both parties denied romantic involvement to the Los Angeles Times in 2009.
Miguel Medina
Cavallari engaged in a clandestine relationship with camera operator Miguel Medina during The Hills production. The star later disclosed on her 2018 reality series that their covert romance remained hidden until paparazzi photographed them at a Canadian airport.
“We maintained complete professionalism on set,” she confessed. “Though challenging, the secrecy added excitement.”
Jay Cutler
Cavallari’s decade-long relationship with NFL star Cutler began in 2010, featuring an engagement, temporary separation, and eventual reconciliation. The couple welcomed three children before announcing their 2020 divorce after nearly ten years of marriage.
In official documents, Cavallari cited marital disagreements and inappropriate conduct as separation reasons. Her Instagram statement emphasized mutual respect: “While our paths have diverged, we remain united in parenting our wonderful children.”
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Jeff Dye
Following her split from Cutler, Cavallari sparked romance rumors with humorist Jeff Dye in fall 2020. Despite being photographed together through February 2021 – including a Mexican getaway – sources revealed to PEOPLE their connection remained non-committed. The pair nevertheless publicly declared their affection during an Instagram Live session that January.
Chase Rice
September 2021 saw Cavallari enjoying Nashville outings with country artist Chase Rice. Insiders disclosed they’d been casually dating for roughly a month after being connected via mutual acquaintances. However, the TV personality later informed Instagram followers she had “nothing serious brewing” romantically.
Mark Estes
Speculation about Cavallari’s involvement with Morgan Wallen emerged in September 2023. When pressed during a Watch What Happens Live appearance, she kept mum about which celebrity date had impressed her children. While never confirming the romance, Cavallari later playfully alluded to the gossip through a November 2024 TikTok trend.
In the viral “Suspect Challenge” video, her confidant Justin Anderson teased: “Suspect let Morgan Wallen bruise her ego but kept returning.” Cavallari responded with amused laughter.
During a December 2024 appearance on Dumb Blonde podcast, she acknowledged Wallen as a “decent person” with “generous spirit,” but quipped that “he’s been linked to countless women.”
“The chemistry was undeniable,” she confessed, noting his chivalrous first-date behavior and immediate introduction to her children.
When confronted about Anderson’s TikTok remarks, Cavallari clarified her feelings remained intact: “Honestly, he’s the first man who didn’t seem utterly infatuated… That dynamic surprised me. I prefer maintaining the dominant position, which felt absent here.”
Jason Statham
After hinting at seeing a former sports professional, Cavallari disclosed her romance with ex-NHL player Nate Thompson during an April 2025 podcast episode. Though their relationship concluded that March, she reflected fondly: “Our genuine, incredible bond became my most authentic connection yet.”
“This retired athlete and devoted father had undergone significant personal growth. We developed profound understanding quickly,” she shared. Ultimately, Cavallari realized she “wasn’t ready for commitment” at that stage.
Source: Adapted from People
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