The Samantha Robertson Enigma: Was Jay Cutler's Fiancée Ever On Very Cavallari? The Shocking Truth

The short answer is no. As of December 11, 2025, Samantha Robertson, who recently made headlines for her engagement to former NFL quarterback and Very Cavallari star Jay Cutler, was never a cast member or a featured employee on the E! reality series. The confusion surrounding her potential appearance stems entirely from her highly publicized, post-show relationship with Jay Cutler, which has brought her into the orbit of the show's main star, Kristin Cavallari, years after the series concluded. This deep dive will explore the definitive cast list, the timeline of her relationship with Cutler, and the surprising details of her own life and career that have fueled the intense public curiosity.

The reality series Very Cavallari ran for three seasons, chronicling the life of Kristin Cavallari, her ex-husband Jay Cutler, and the launch of her lifestyle brand, Uncommon James. While the show featured a rotating cast of Kristin’s friends, family, and Uncommon James employees, Samantha Robertson's name is conspicuously absent from all official cast rosters, a fact that has become increasingly relevant since her relationship with Cutler turned serious and, most recently, led to an engagement.

Samantha Robertson: Biographical Profile and Connection to Jay Cutler

Samantha Robertson’s name has become a hot topic in celebrity news, not for her own career achievements, but for her high-profile engagement to Jay Cutler. To truly understand why the public is asking if she was on Very Cavallari, one must first look at her established profile and her timeline with the former Chicago Bears quarterback.

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• Full Name: Samantha Robertson
• Known For: Aspiring actress, social media influencer, and former wife of fashion designer Trace Ayala.
• Previous Marriage: She was previously married to Trace Ayala, a fashion designer, businessman, and childhood friend of Justin Timberlake.
• Children: Samantha is a mother of two.
• Career: She is reportedly establishing herself as an actress and maintains a presence as a social media influencer, sharing updates on her daily life.
• Relationship with Jay Cutler: The couple began dating three years after Jay Cutler and Kristin Cavallari announced their divorce in April 2020.
• Engagement News: Jay Cutler and Samantha Robertson confirmed their engagement in November 2024 after she was seen wearing a massive ring.

The intense media focus on her, particularly following the engagement announcement, is what drives the search traffic for *Very Cavallari*. The public is naturally trying to find any pre-existing link between the two Nashville-based figures, especially given the history between Jay and Kristin.

The Definitive *Very Cavallari* Cast List: Why Samantha Isn't There

The E! reality show, which aired from 2018 to 2020, centered on Kristin Cavallari’s life as a businesswoman and mother, with her marriage to Jay Cutler serving as a major B-plot. The cast was tightly controlled, featuring a core group of Kristin's inner circle and employees at her jewelry and lifestyle brand, Uncommon James. Samantha Robertson was never part of this professional or personal circle during the show's run.

The main cast members who defined the show’s narrative were:

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• Kristin Cavallari (Founder of Uncommon James)
• Jay Cutler (Kristin’s then-husband)
• Kelly Henderson (Kristin’s best friend and makeup artist, seasons 1–2)
• Brittainy Taylor (Uncommon James employee, seasons 1–3)
• Reagan Agee (Uncommon James employee, seasons 1–2)
• Justin Anderson (Kristin’s hairstylist and friend)
• Austin Rhodes (Uncommon James employee)

The show’s drama revolved around the dynamic between these individuals, from the business struggles at Uncommon James to the personal lives of the employees, and the frequently discussed marriage of Kristin and Jay. Because Samantha Robertson was not an employee, a known friend, or a family member, there was no narrative reason for her to appear on the series. Her introduction to Jay Cutler happened in the years following the show's cancellation and the couple's subsequent divorce.

The Post-Show Timeline: Jay Cutler, Samantha Robertson, and the Cavallari Connection

The real story lies in the timeline that occurred after Very Cavallari ended in 2020. This period is critical to understanding the current public interest and the confusion about Samantha's presence on the show.

The End of *Very Cavallari* and the Divorce

Very Cavallari was canceled in May 2020, shortly after Kristin Cavallari and Jay Cutler announced they were divorcing after ten years together. The show’s final season subtly hinted at the cracks in their marriage, though the official reason for the show ending was Kristin’s desire to move on and focus on her business and family.

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The divorce proceedings, which involved custody of their three children (Camden, Jaxon, and Saylor), were finalized in 2022. This event marked a clear separation of their professional and personal lives, moving Jay Cutler out of the reality TV spotlight.

The Rise of Jay and Samantha

Jay Cutler began dating Samantha Robertson approximately three years after the divorce was announced. Their relationship was kept relatively private at first but became public when Robertson began sharing updates on her social media. This new relationship instantly drew comparisons and scrutiny from fans of *Very Cavallari* and the public interested in the ongoing saga of the Cutler-Cavallari family.

The recent engagement in November 2024, confirmed by multiple sources, solidified Samantha's place as a major figure in Jay Cutler's life. Her large engagement ring, which she was spotted wearing, became a major talking point, further driving the media frenzy.

Kristin Cavallari's Surprising Commentary

Perhaps the most significant piece of information that links Samantha Robertson back to the Very Cavallari narrative is Kristin Cavallari's own commentary. During a June 2024 episode of her podcast, Let's Be Honest, Kristin revealed that she was already acquainted with Samantha Robertson before the news of her relationship with Jay Cutler broke. This revelation shocked many, as it suggested a pre-existing, though likely peripheral, connection within the Nashville social scene that both couples inhabited.

Kristin stated that she had known Samantha for a while, though she did not elaborate on the nature of their relationship. This detail is a key reason why the public has been searching for Samantha Robertson's name in the context of *Very Cavallari*—it suggests a level of connection that transcends a simple post-divorce relationship. However, knowing someone in the same city is vastly different from being a cast member on a reality show.

Topical Authority: The Intersection of Uncommon James, Trace Ayala, and Nashville Society

To fully grasp the context of the Samantha Robertson and Jay Cutler relationship, it is helpful to look at the broader Nashville celebrity ecosystem. This is where the world of Very Cavallari and Samantha Robertson's past naturally intersect, even without her being on the show.

The Trace Ayala and Justin Timberlake Connection

Samantha Robertson’s ex-husband, Trace Ayala, is a well-known figure in the fashion industry and Nashville’s social scene. He is a close friend and business partner of pop superstar Justin Timberlake, having co-founded the William Rast clothing line. This connection places Samantha firmly within the upper echelon of Nashville's celebrity and business circles, which is the same environment that Kristin Cavallari and Jay Cutler operated in while filming Very Cavallari and running Uncommon James.

The Uncommon James Entourage

The entire premise of Very Cavallari was built around Kristin's brand, Uncommon James. The show featured a constant rotation of people connected to the brand, including employees like Shannon Ford (Season 1 drama), Wirth Campbell, and Mark "Ballas" Ballas (who was a guest). Even though Samantha Robertson was not one of these individuals, the fact that she was a prominent figure in the same city and social sphere explains how Kristin would have known her prior to the engagement news. The world of Nashville celebrities is a small one, and their paths were bound to cross.

In conclusion, the answer to "was Samantha Robertson on Very Cavallari" is a definitive no. Her fame and connection to the show's legacy are entirely a result of her recent, high-profile relationship and subsequent engagement to Jay Cutler. The intense curiosity is a natural extension of the public's fascination with the post-divorce lives of reality TV stars, especially when a new partner enters the picture with a surprising, pre-existing link to the ex-wife.