Kristin Cavallari attends the Uncommon James SS20 Launch Party (left); Jay Cutler attends the JDRF LA 2015 Imagine Gala at the Hyatt Regency Century Plaza on May 9, 2015 (right). Photo: Tibrina Hobson/Getty; Todd Williamson/Getty
Kristin Cavallari has revealed new details about her emotional split from Jay Cutler and how their relationship has evolved since their divorce. On October 22, 2024, during the latest episode of her podcast Let’s Be Honest, the Laguna Beach alum candidly reflected on the end of her marriage and the heartbreak she experienced in the years leading up to her 2020 divorce from the former NFL star. Cavallari, 37, described the separation as a painful but necessary decision, one that left her heartbroken despite being the one to initiate it.
The podcast aired just days after news broke that Cutler, 41, had been arrested in Tennessee on charges of driving under the influence and illegal possession of a firearm while intoxicated on October 18. Cavallari addressed the timing of the episode, clarifying that she recorded it before her ex-husband’s public incident. While she made it clear that she had no intention of commenting on the arrest, she expressed that she wishes Cutler well and hopes he seeks the help he needs.
Reflecting on their time together, Cavallari shared that her marriage had been troubled for years before the divorce. “My heart broke in my marriage. Even though I’m the one that walked away, it was not what I wanted,” she admitted. Cavallari emphasized how deeply she had tried to save the relationship but ultimately couldn’t make it work. “It’s just heartbreaking when you want something so badly but you just can’t get there. And I would say my heart was broken for years in my marriage.”
Although the couple had faced public scrutiny during and after their marriage, Cavallari was quick to clarify that her current reflections were not meant to disparage Cutler. She acknowledged that she had previously spoken openly about their struggles but now chooses to remain mostly silent on the topic. “I’m not talking negatively about Jay at all. I’m really not,” she said. “But I will say, we are in the best place that we’ve been in.”
Cavallari shared that it took over four years for them to reach a point where they could co-parent peacefully. She recalled a recent instance where the two sat together at their son Camden’s basketball game, something she never imagined happening so amicably. “Things are really good with us now… it makes me so happy because honestly, I never thought that we would get there. I really didn’t.”
Cavallari used her own experience as an example for her listeners who may be facing similar co-parenting challenges. “If Jay and I can get there, anyone can get there,” she said with optimism. Despite not going into further detail, she reassured her audience that the progress they’ve made is real and significant.
Cavallari and Cutler, who were married in 2013 and share three children—Camden, Jaxon, and Saylor—have come a long way since their highly publicized split. Their ability to co-parent effectively, despite the ups and downs of their past, is something that Cavallari is clearly proud of.
The podcast episode also touched on Cavallari’s recent breakup with Montana Boyz actor Mark Estes. The pair, who had been dating for seven months, called it quits in September 2024. Cavallari, who is 13 years older than Estes, explained that the age difference played a role in their separation. “He’s been the best boyfriend I’ve ever had, but I just know long-term it’s not right,” she said on the podcast. “He needs to experience life, he’s young.”
According to sources, there was no drama behind the split, but rather a mutual understanding that they were heading in different directions. Cavallari’s candid approach to both her past and present relationships has become a hallmark of her podcast, offering fans a rare glimpse into her personal life while emphasizing growth, acceptance, and moving forward.
Jay Cutler, meanwhile, has been linked to Samantha Robertson since last year. The pair went public with their relationship on Instagram in September 2023, but have largely kept their romance out of the spotlight. Neither Cutler nor Robertson has publicly commented on the nature of their relationship since his recent arrest.
While Kristin Cavallari may have experienced heartbreak in her marriage, her reflections show that she’s found peace with her past and is focused on creating a stable, happy future for herself and her children. With her podcast, she continues to inspire listeners by sharing both the highs and lows of her journey, always maintaining a message of resilience and hope.
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