Kristin Cavallari recently opened up about a painful financial lesson learned during her early adulthood involving her father, Dennis Cavallari. On an episode of her podcast “Let’s Be Honest with Kristin Cavallari,” the television personality reflected on how lending her father a substantial sum of money has left her “in the hole” to the tune of $250,000.
A Risky Financial Move
The 39-year-old entrepreneur shared that the incident took place when she was just 22 years old, while she was filming “The Hills.” “My dad came to me… and asked for a large sum of money to borrow. Six figures,” she recalled. At that time, although she was making a considerable income, taking out such a large loan was still daunting for her.
Unfulfilled Promises
Kristin recounted her father’s promise to return the borrowed money within a few months, complete with interest. However, he never repaid the first loan and instead asked for another loan of the same magnitude. “He probably said six months, and he was going to give me interest on top of it. And, you know, well, I didn’t get paid back,” she stated candidly.
When she confronted him about the unpaid loan, Kristin ultimately chose to lend him more money despite her reservations. “I said to him, ‘You haven’t even acknowledged the first payment, and now you want more money?’” she explained, identifying her past naivety as a significant factor in her decision. “But because I’m such a f—–g sucker — or I was at the time — I lent him more money,” she admitted.
A Lesson in Boundaries
Reflecting on this experience, Cavallari expressed that she no longer holds any expectations of being repaid. “I will never see that money,” she remarked. This realization led her to understand the importance of financial boundaries, especially when it involves family. “Talk about a bad business decision,” she noted, illustrating how the financial misstep shaped her approach to lending money in the future.
Understanding the Consequences
Kristin elaborated on how having money can sometimes breed expectation, particularly among family members. “When you have money, it’s almost like people expect it,” she expressed, making it clear that being financially secure doesn’t mean one is obligated to lend out their hard-earned money. The past experience has now motivated Cavallari to instill financial literacy in her children. “I can’t imagine going to my kids when they’re 22 and asking for that kind of money,” she shared, expressing disbelief over her father’s request.
Moving Forward
As a mother of three, Cavallari has since learned to set firmer boundaries and recognize the importance of self-advocacy. “I didn’t know how to set boundaries in my early 20s,” she said. She also mentioned that this incident has prompted her to contemplate how she wants to teach her children about money and financial responsibility.
In a subsequent appearance on the “Aspire with Emma Grede” podcast, Cavallari came to terms with the financial loss, stating she had ultimately found peace with it. Yet, the relationship with her father remains complex and unsatisfactory. “I’ve ultimately cut my dad out of my life,” she revealed, indicating that the financial betrayal was only part of their ongoing misunderstandings.
Now, with her focus on educating women about financial independence and the lessons she learned along the way, Kristin highlights the importance of talking openly about money. “I’m over money being a taboo topic for women,” she proclaimed, using her podcast platform to encourage financial discussions among women and reflecting on her personal journey of growth.





