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7 Shocking Updates On Kristin Cavallari And Jay Cutler’s Post-Divorce Life: The Custody Battle, New Engagements, And 'Slander' Claims

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The highly-publicized divorce of reality star Kristin Cavallari and former NFL quarterback Jay Cutler continues to make headlines, with the former couple navigating a complex and often contentious post-marital life. Their relationship, which was chronicled on the E! reality series Very Cavallari, ended in 2020, but the drama surrounding co-parenting and financial settlements remains a hot topic, especially with new, fresh details emerging in late 2025. This article dives deep into the most recent updates, including a public feud over the divorce money and their dramatically different dating lives today, as of December 2025.

The core of their ongoing story revolves around their three children and their individual paths to finding new love. While one has moved on to an engagement, the other is openly discussing a dating "dry spell." Furthermore, a recent, highly-publicized dispute over the financial terms of their separation has brought their post-divorce relationship back into the spotlight, proving that even years after the split, the final chapter is far from written.

Kristin Cavallari and Jay Cutler: A Complete Profile and Biography

Before their tumultuous divorce, Kristin Cavallari and Jay Cutler were one of the most visible celebrity couples in both reality television and professional sports. Their careers have evolved significantly since their time together, with both finding new ventures in media and entrepreneurship.

Kristin Cavallari: Reality Star, Designer, and Entrepreneur

  • Full Name: Kristin Elizabeth Cavallari
  • Born: January 5, 1987, in Denver, Colorado
  • Career Highlights: Rose to fame at age 17 on the MTV reality series Laguna Beach: The Real Orange County (2004). She later starred in the spin-off The Hills and her own E! reality show, Very Cavallari (2018–2020).
  • Current Ventures: Founder and CEO of the lifestyle brand Uncommon James, which specializes in jewelry, home goods, and skincare. She is also the host of the popular podcast, Let's Be Honest.
  • Children: Sons Camden Jack (b. 2012), Jaxon Wyatt (b. 2014), and daughter Saylor James (b. 2015).

Jay Cutler: NFL Quarterback and Media Personality

  • Full Name: Jay Christopher Cutler
  • Born: April 29, 1983, in Santa Claus, Indiana
  • Career Highlights: Former American professional football quarterback who played 12 seasons in the National Football League (NFL). He was drafted by the Denver Broncos in 2006 and is best known for his time as the starting quarterback for the Chicago Bears (2009–2016). His career stats include 35,133 passing yards and 227 touchdowns.
  • Current Ventures: Host of the podcast Uncut with Jay Cutler and is involved in various business projects, including his own supplement brand.
  • Children: Sons Camden Jack, Jaxon Wyatt, and daughter Saylor James.

The Public Feud Over the Divorce Settlement: 'Borderline Slander'

One of the most surprising and recent developments in the Cavallari-Cutler saga is a public dispute over the financial details of their divorce, which was finalized in 2022. The controversy began when Kristin Cavallari suggested on her podcast that she received no financial settlement from Jay Cutler.

In a strongly worded response on his own Take It Outside podcast in August 2025, Jay Cutler vehemently refuted her claims. He stated that Kristin's assertion that she "didn't get a dime" was "reckless" and "borderline slander," making it clear that a substantial financial settlement was indeed part of their final agreement. This public back-and-forth highlights the deep-seated tension that still exists between the ex-couple, despite their attempts to maintain a civil front for their children.

The dispute centers on the division of marital assets accumulated during their seven-year marriage. While the exact details of the settlement remain private, Cutler's public statement confirms that the reality star did receive funds, directly contradicting her on-air comments.

Co-Parenting Challenges and the New Custody Agreement

Since their separation, the former couple has been vocal about the difficulties of co-parenting their three children. Kristin has frequently described the dynamic as "inconsistent" and "challenging" over the years.

However, a significant legal update occurred in late 2024 when Kristin shared news of a new custody agreement on her Let's Be Honest podcast. Under the new terms, Kristin Cavallari has retained primary physical custody of the children—Camden, Jaxon, and Saylor. This structural change was described by Cavallari as a positive step toward establishing a more stable and predictable routine for the children, moving away from the previous, more fluid arrangement.

This new agreement is a crucial entity in their current relationship, as it legally defines their interactions and responsibilities. The shift underscores the reality that while the romantic relationship is over, the co-parenting partnership—however difficult—is a permanent fixture in their lives.

Dramatically Different Dating Lives in 2025

The dating lives of Kristin Cavallari and Jay Cutler have taken markedly different, yet equally public, trajectories in 2025.

Jay Cutler: Engaged to Samantha Robertson

Jay Cutler has officially moved on and is now engaged. He went Instagram official with his partner, Samantha Robertson, in September 2023. Robertson, who is a mother herself, has been widely accepted as Cutler's new chapter, with the engagement marking a serious commitment two years after his divorce was finalized.

Robertson has been described as a successful businesswoman, and their relationship has been notably more private than Cutler’s marriage to Cavallari, which was heavily documented on reality television. This new relationship seems to signal a desire for a more low-key life away from the intense media scrutiny of his previous marriage.

Kristin Cavallari: The 'Dry Spell' and the Mystery Date

In contrast, Kristin Cavallari has been very candid about her struggles returning to the dating pool. In the first half of 2025, she openly discussed her "lack of" sex life, calling her dating dry spell "really sad." She has been on a journey of self-discovery and prioritizing her children and business, Uncommon James, over a serious relationship.

However, her dating life recently "picked back up." On her podcast, she teased details about a recent date with a new man, whom she described as a "big deal," though she refused to reveal his identity. She has also had to actively shut down rumors, denying that she is dating a specific "A-lister," clarifying recent headlines that have surfaced in the media. Cavallari maintains that she is enjoying the dating game but is not rushing into anything serious, a stark contrast to her ex-husband's new engagement.

The ongoing narrative of Kristin Cavallari and Jay Cutler remains one of two high-profile individuals navigating the complexities of modern co-parenting while each pursuing happiness on their own terms. From public financial disputes to new custody arrangements and divergent romantic paths, their story continues to captivate fans who followed their journey from the beaches of Laguna Beach to the fields of the NFL.

kristin cavallari and jay cutler
kristin cavallari and jay cutler

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