Kristin Cavallari Reveals Her Biggest Regret From Romance With Ex Mark Estes

During a brutally honest podcast chat with Chelsea Handler, the reality star admitted there is one aspect of the relationship she still regrets — and it has everything to do with who picked up the bill.

Kristin Cavallari has never shied away from speaking candidly about her relationships, and her latest revelation may be one of her most unfiltered yet.

What started as a conversation about paying for dates quickly turned into a surprisingly personal confession about Cavallari's former relationship with social media personality Mark Estes.

Kristin Cavallari Says Paying for Her Younger Ex Became a Major Regret

On the May 26, 2026, episode of her "Let's Be Honest" podcast, Cavallari sat down with Chelsea Handler for a candid discussion about dating dynamics and finances in relationships.

During the conversation, the two agreed that constantly paying for a romantic partner can eventually create resentment. "You think you can do it, and that it's okay, and then you're like, 'I don't respect you,'" Handler said during the conversation.

Cavallari immediately agreed before revealing that she largely funded her seven-month relationship with Estes, who was 24 when they started dating in 2024. Cavallari shared:

"The younger guy that I dated, I paid for everything, and understandably so, he was 24."

Still, the 39-year-old admitted there is one memory from the relationship that continues to irritate her: the lavish trips and expenses she covered during their time together.

Cavallari specifically recalled paying for their getaway to Greece shortly before the couple split. She joked that Estes even managed to burn through a significant amount of her American Express reward points during the relationship.

"He took, like, half my Amex points," she said with a laugh before admitting the situation "still pisses" her off. Handler attempted to lighten the mood by telling Cavallari to view the relationship as "renting a good time," a comment that made the podcast host burst into laughter.

Their Split Was Linked to Different Priorities

Cavallari and Estes first went public with their relationship in February 2024. Their romance quickly became a talking point online because of their 13-year age difference.

The pair ultimately split seven months later, with sources close to the former couple saying they were simply moving in different directions. Insiders also noted that the age gap contributed to the breakup, although there was reportedly no major drama between them.

Despite her latest frustrations, Cavallari previously spoke highly of Estes after their breakup. She described the relationship as "very healthy and very mature," and even called him "the best boyfriend" she had ever had.

At the time, Cavallari explained that she ultimately ended the relationship because she knew it was not right for her long-term future.

Following the breakup, the reality star briefly dated retired hockey player Nate Thompson, whom she later described as one of the most genuine connections she had experienced. Since then, Cavallari has largely kept her dating life private.

Estes, meanwhile, moved on with influencer Sommer Ray in 2025. Even so, Kristin Cavallari's latest comments suggest at least one part of her relationship with the TikTok star still lives rent-free in her mind — especially those missing Amex points.