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From TikToker To NHL Star: The 5 Biggest Surprises In Kristin Cavallari's Dating History

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Kristin Cavallari's dating life has been a constant source of public fascination since her days on Laguna Beach. The mother-of-three, reality TV star, and entrepreneur has navigated the complex world of post-divorce romance with candor, making headlines in late 2024 and early 2025 for her surprising shift in partner preference, moving from a much younger TikTok star back to a mature, established athlete.

The star of *The Hills* has been remarkably open about her journey, using her popular podcast, Let's Be Honest, to share the intimate details of her relationships, including the real reason behind her high-profile 2024 breakup and the exciting new chapter she is currently embarking on.

Kristin Cavallari: The Full Biography and Profile

Kristin Cavallari is a multi-hyphenate star whose career has spanned reality television, fashion, and business. She first gained fame as a high school student on the hit MTV reality series, Laguna Beach: The Real Orange County, which chronicled her relationships with co-stars Stephen Colletti and Talan Torriero.

  • Full Name: Kristin Elizabeth Cavallari
  • Date of Birth: January 5, 1987
  • Age (as of December 2025): 38
  • Hometown: Denver, Colorado, U.S.
  • Notable Education: Laguna Beach High School
  • Children: Three (with ex-husband Jay Cutler) - Sons Camden Jack and Jaxon Wyatt, and daughter Saylor James.
  • Ex-Husband: Jay Cutler (Former NFL Quarterback), married 2013, divorced 2020.
  • Career: Reality TV Star (*Laguna Beach*, *The Hills*, *Very Cavallari*), Fashion Designer, Entrepreneur (Founder of Uncommon James jewelry and Little James clothing), Author.
  • Podcast: Let's Be Honest with Kristin Cavallari

The Mark Estes Era: The 13-Year Age Gap and The Breakup

One of the most talked-about chapters in Kristin Cavallari's recent dating history was her relationship with Mark Estes. Their romance became official on Valentine's Day 2024 when Cavallari went Instagram official with the 24-year-old model and social media personality while vacationing in Mexico.

The relationship immediately drew public attention due to the significant 13-year age difference, with Cavallari being 37 at the time. Mark Estes is best known as a member of the Montana Boyz, a viral TikTok content creation crew known for their "cowboy influencer" aesthetic.

The 'Best Boyfriend' Who Needed to 'Experience Life'

Despite the age gap, Cavallari was initially effusive about the relationship, describing Estes as "the best boyfriend" she had ever had during an October 2024 episode of her podcast.

However, the romance was short-lived. After about seven months of dating, Cavallari confirmed they had broken up. She was candid about the reason for the split, explaining that it was solely due to the age difference and not a lack of love or a bad incident.

“I just know long-term he needs to experience life,” Cavallari explained, stating that she broke up with Mark because she knew long-term the relationship was not right for his stage of life.

Back to Athletes: Who is Kristin Cavallari Dating Now?

Following her split from Mark Estes, Kristin Cavallari has made a significant and intentional shift in her dating strategy, seeking out men who are older, more established, and have children of their own, aligning with her life stage as a mother of three.

In a late December 2024 update, Cavallari confirmed she is officially dating someone new and would not be single heading into 2025. She revealed that her new partner is a 40-year-old retired athlete who is also a father with children from a previous relationship.

This news signals a return to her comfort zone, as she was previously married to former NFL quarterback Jay Cutler and has a history of dating professional athletes.

The Mystery Man and the NHL Connection

While the name of her new 40-year-old boyfriend was not immediately disclosed in the late 2024 announcements, Cavallari has previously been open about a "deep" connection she had with a man who perfectly fits this description: former NHL player Nate Thompson.

Thompson, who is 40 years old and a father, was revealed by Cavallari on her podcast in April 2024 as the "mystery athlete" she had been seeing. She described the relationship as "the most honest, pure, amazing, quote-unquote fling" she had ever had.

Given the specific details—a 40-year-old retired athlete and a father—many speculate that the retired NHL star Nate Thompson is the new man in her life, or at least the type of mature, established partner she is now prioritizing. The focus on a man in his 40s with kids suggests Cavallari is looking for a partner who understands the complexities of co-parenting and a post-professional career life.

A Look Back: Kristin Cavallari's Full Dating History (Key Entities)

Kristin Cavallari's love life has been a whirlwind of high-profile relationships, often with athletes and fellow reality stars. Her dating history provides a roadmap of her personal growth and changing priorities.

  • Stephen Colletti (2004): Her on-again, off-again high school sweetheart, famously documented on Laguna Beach. They remain close friends and co-host the *Back to the Beach* podcast.
  • Talan Torriero (2004): Another high school fling that played out on Laguna Beach.
  • Matt Leinart (2004): Briefly linked to the former USC quarterback and Heisman Trophy winner.
  • Brody Jenner (2005-2006): A high-profile relationship that was featured during her time on *The Hills*.
  • Nick Zano (2006-2007): Dated the actor known for *What I Like About You*.
  • Jay Cutler (2010-2020): Her ex-husband and the father of her three children. Their decade-long relationship, marriage, and eventual divorce were a major part of her life and the focus of her show *Very Cavallari*.
  • Jeff Dye (2020): Briefly dated the comedian following her separation from Cutler.
  • Chase Rice (2021): Linked to the country music singer for a brief romance in Nashville.
  • Mark Estes (2024): The TikTok star and model, 13 years her junior, whose relationship ended due to the age gap.
  • Nate Thompson (2024): The retired NHL player and father of two who she described as having a "deep" connection with. He is a key entity in her shift toward dating older, established men.

The Key Takeaway: A Focus on Maturity and Alignment

Kristin Cavallari's journey through dating in 2024 highlights a clear evolution in her priorities. While the relationship with Mark Estes was a fun, passionate moment in her life, she ultimately prioritized long-term compatibility and maturity. Her decision to end the romance with the younger Estes to pursue a relationship with a 40-year-old retired athlete underscores her commitment to finding a partner who is aligned with her life as a successful entrepreneur and a dedicated mother. The reality star is now focused on a serious, stable future, proving that for her, true connection trumps celebrity status or social media fame.

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