Jay Cutler And Kristin Cavallari: 5 Shocking New Updates On Their Lives After Divorce (2025)

The tumultuous relationship and high-profile divorce of former NFL quarterback Jay Cutler and reality star Kristin Cavallari continues to be a source of intense public fascination, even years after their split. As of late 2025, both stars have navigated significant personal and professional changes, moving past the dissolution of their seven-year marriage. The latest news provides a fresh look into their separate lives, revealing a new engagement for Cutler, a major update on their co-parenting dynamic, and Cavallari's surprisingly candid confession about her dating life.

Their journey from a whirlwind romance, marriage in 2013, and the eventual filing for divorce in 2020 has culminated in a carefully managed co-parenting arrangement for their three children. The most recent headlines from mid-to-late 2025 confirm that while they maintain a cordial relationship for the sake of their family, their paths are diverging dramatically, marked by new partners, business ventures like Uncommon James and CUTS Meat, and the ongoing complexities of their post-split financial and custody agreements.

The Complete Profile: Jay Cutler and Kristin Cavallari Biography

The former couple, known for their roles in sports and television, respectively, have built successful careers both together and apart. Their biographies highlight the distinct worlds they occupied before and after their relationship.

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• Kristin Cavallari (Reality Star, Entrepreneur)
  • Born: January 5, 1987 (Denver, Colorado)
  • Career Highlights: Rose to fame on the MTV reality show Laguna Beach: The Real Orange County (2004–2005), followed by The Hills. She later starred in her own E! reality series, Very Cavallari (2018–2020).
  • Business Ventures: Founder and CEO of the successful lifestyle brand Uncommon James, which sells jewelry, homeware, and beauty products. She is also a published author.
  • Current Status (2025): Focused on her business, podcast Let's Be Honest, and co-parenting.
• Jay Cutler (Former NFL Quarterback)
  • Born: April 29, 1983 (Santa Claus, Indiana)
  • Career Highlights: Collegiate football at Vanderbilt University. Drafted by the Denver Broncos in 2006. Best known for his tenure as the starting quarterback for the Chicago Bears (2009–2016). Also played for the Miami Dolphins.
  • Business Ventures: Launched the premium meat subscription service and butcher shop, CUTS Meat, often collaborating with celebrity butcher Pat LaFrieda.
  • Current Status (2025): Engaged to Samantha Robertson and managing his business interests. Recently faced legal issues regarding a DUI charge.

The couple shares three children: sons Camden Jack (born 2012) and Jaxon Wyatt (born 2014), and daughter Saylor James (born 2015).

5 Shocking New Updates on Jay and Kristin's Post-Divorce Life

The finalization of their divorce in 2022 marked the end of their marital relationship, but the headlines keep coming. The year 2025 has proven to be a pivotal time, bringing major developments in their personal lives, from new relationships to candid confessions.

1. Jay Cutler is Reportedly Engaged to Samantha Robertson

In one of the biggest post-divorce updates, former Chicago Bears star Jay Cutler is reportedly engaged to his girlfriend, Samantha Robertson. The news of their relationship first became public when the couple went "Instagram official" in September 2023. Robertson, a mother herself, marks Cutler’s first major public relationship since his split from Cavallari. This development confirms that while Cutler has maintained a relatively private life since retiring from the NFL, his personal life is moving forward rapidly, leading to speculation about wedding plans and the blending of their families.

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2. Kristin Cavallari Retains Primary Physical Custody of the Children

A significant point of contention during and after the divorce was the custody of their three young children. In a major update shared by Kristin Cavallari in mid-2025, she set the record straight on her podcast, Let's Be Honest. Cavallari revealed a recent change in their custody agreement, confirming that she has retained primary physical custody of Camden, Jaxon, and Saylor. This arrangement, while allowing Jay Cutler substantial visitation, solidifies Cavallari's role as the primary caregiver, a dynamic she has often spoken about on her podcast.

3. Kristin Calls Her 2025 Dating Life a 'Really Sad' Dry Spell

Despite being a highly sought-after celebrity, Kristin Cavallari was surprisingly honest about her dating struggles in the first half of 2025. She candidly described her dating life as being in a "dry spell" and confessed to a "lack of sex," calling the situation "really sad." This admission counters the typical celebrity narrative and highlights the difficulty of dating as a high-profile, divorced mother of three. While she had previously teased dating a new man—a 40-year-old retired athlete and father—she later clarified rumors and revealed she had put a temporary pause on dating altogether to focus on herself and her children.

4. The Financial Fallout and Divorce Settlement Disagreement

The finalization of their divorce in 2022 was complex, involving significant assets, including their Nashville homes and the businesses they built during their marriage. In a recent development, Jay Cutler publicly denied claims made by Cavallari that she "didn't get a penny" from the divorce settlement. While the exact details of the financial settlement remain largely private, this public disagreement underscores the lingering tension over their shared assets and the division of wealth accumulated during their time together, especially concerning their respective entrepreneurial endeavors like Uncommon James and CUTS Meat.

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5. Jay Cutler’s Recent Legal Troubles

Adding another layer of complexity to the former quarterback's life, Jay Cutler recently faced legal issues, including a DUI charge that resulted in jail time. While the specifics of the incident and the exact timing are part of a separate legal matter, the news became a significant headline, reminding the public that both individuals continue to navigate personal challenges while managing their public profiles and co-parenting responsibilities. These developments highlight the differing personal trajectories of the former couple in 2025.

Co-Parenting, Custody, and the Future of the Cutler-Cavallari Family

The primary focus for both Jay Cutler and Kristin Cavallari remains their three children: Camden Jack, Jaxon Wyatt, and Saylor James. Both have publicly emphasized the importance of maintaining a united front and a cordial relationship to ensure a stable environment for their family. This commitment to effective co-parenting is arguably the most successful aspect of their post-divorce dynamic.

Cavallari frequently uses her podcast to discuss the realities of co-parenting, often praising Cutler for their ability to communicate effectively, despite their differences. The recent custody update, which sees Cavallari retaining primary physical custody, is a testament to the structure they have established. This structure allows the children to thrive in Nashville, a city where both parents have deep roots and established business interests.

The future for the Cutler-Cavallari family is now one of two distinct, yet interconnected, paths. Jay Cutler is moving toward a new chapter with his fiancée, Samantha Robertson, which will inevitably involve integrating his children into a new blended family dynamic. Meanwhile, Kristin Cavallari is focused on her professional growth with Uncommon James and her personal well-being, taking a deliberate pause from dating to prioritize her own mental and emotional health. Their story serves as a high-profile example of how celebrity couples navigate the complexities of divorce, finances, new relationships, and the paramount responsibility of raising children in the public eye.