Kristin Cavallari, the well-known television personality and entrepreneur, has opened up about her relationship with Mark Estes, a social media influencer who is 13 years her junior. The couple dated for a brief period of seven months in 2024, during which Cavallari reveals she took on a significant financial burden in the relationship.
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In a candid discussion on her podcast, “Let’s Be Honest”, which aired on May 26, Cavallari spoke with guest Chelsea Handler about the dynamics of relationships involving financial contributions. The 39-year-old revealed that her experiences with Estes still linger on her mind, particularly the aspect of her financially supporting him during their time together.
Cavallari recounted that she had paid for a number of their outings, including an expensive trip to Greece, stating, “That’s like the one thing that I look back and it, like, pisses me off that I paid … to [go to] Greece and, like, all these things.” She further expressed her frustration about having to use her American Express points for their travels, exclaiming, “He took, like, half my Amex points; I’m like, f—er. It still pisses me off to this day.”
Handler joined in the discussion, adding that she finds it disconcerting when women have to take on the financial responsibilities in a relationship, to which Cavallari agreed, saying it can lead to a lack of respect. This exploration of their dynamic ultimately prompted Cavallari to reflect on her regret about the imbalance in their financial contributions.
Despite the financial strain, Cavallari regarded her relationship with Estes as a high point in her romantic life, referring to him as “the best boyfriend I’ve ever had.” However, she acknowledged that their age difference created challenges, and ultimately, the couple decided to part ways, citing that they were “heading in different directions.”
Sources close to the couple indicated that the age gap played a role in their split, with Cavallari realising, albeit reluctantly, that long-term compatibility would be difficult to maintain. She described the relationship as “the best relationship of my life,” noting it was “very healthy and very mature,” demonstrating the complexity of her feelings surrounding the breakup.
Following her separation from Estes, Cavallari ventured into a short-lived romance with retired athlete Nate Thompson, during which she expressed that their time together was marked by honesty and purity, labelling it “the most honest, pure, amazing, quote-unquote ‘relationship’ I’ve ever had.” Since then, Cavallari seems to have kept her romantic life private, indicating a desire for reflection and perhaps a break from the intensity of public scrutiny.
Meanwhile, Estes has since moved on and is currently in a relationship with influencer Sommer Ray, beginning their romance in June 2025. As both individuals explore new chapters in their lives, they carry with them the lessons learned from their previous relationship.
Cavallari’s openness about her experiences serves as a reminder of the inherent complexities in modern relationships, especially those involving significant age disparities. Her willingness to discuss both the joyful and challenging aspects of her former romance with Estes resonates with many who have navigated similar dynamics, making for a relatable dialogue in the realm of contemporary relationships.