Kristin Cavallari Owes $250K After Father Borrowed Money Twice

Kristin Cavallari is digging into a painful lesson after giving her father a quarter of a million dollars that never came back. She recently opened up on her podcast "Let's Be Honest with Kristin Cavallari" to discuss women and finances. The 39-year-old reality star admitted she ended up $250,000 in debt because two loans to Dennis Cavallari were never repaid.

"My dad came to me," Cavallari said. "I was filming 'The Hills,' so I must have been 22." She asked for a large sum of money to borrow. Six figures is what she needed back then. "And I was making great money at the time, but it's still, I'm 22," she continued. "Six figures is a big deal for me."

She lent the cash and he promised repayment. He probably said six months and offered interest on top of it. That promise didn't hold up. Instead, he asked to borrow more money. Another six-figure number came down the pipe. She confronted Dennis about the unpaid first loan but ultimately relented. "I said to him, 'You haven't even acknowledged the first payment, and now you want more money?'" she recalled. But because I'm such a f-----g sucker, or I was at the time, I lent him more money.

The "Laguna Beach" alum admitted she has no expectation of ever getting the money back. "I will never see that money," she said. She is in the hole with her own dad, a quarter of a million dollars total. Talk about a bad business decision. However, the TV personality acknowledged that the experience taught her the importance of setting boundaries with family and friends when it comes to money.

"I didn't know how to set boundaries in my early 20s," she admitted. "I've learned that." It would be a very different conversation probably today, but it is the lending-money-to-people thing. When you have money, it's almost like people expect it. You are in no way, shape or form required or obligated to lend anybody money, especially if you've worked your f---king tail off for that money. Like I have worked my ass off for all of my money. And so I think that's why probably that stings the most. It just was like sort of taking advantage of me at such a young age.

Now a mother herself, Cavallari said she struggles to understand her father's decision to turn to her for such a large sum when she was so young. She shares sons Camden, 14, and Jaxon, 12, and daughter Saylor, 10 with her ex-husband, former NFL quarterback Jay Cutler. I can't imagine going to my kids when they're 22 and asking for that kind of money, she said. I guess I understand that he didn't have a lot of options. But I don't know. And also my relationship with my dad is very complicated. So there are other layers to it. But for the purpose of this conversation, I just think you're allowed to do what you want to do with your money.

Cavallari shared a clip from the episode on Instagram, emphasizing the importance of financial literacy for women. We're talking all things MONEY this week, she wrote in her caption. She is over money being a taboo topic for women. They are talking financial independence, the mistakes I've made, and everything I've learned along the way.

If you wanna chase the bag, this one's for you." That catchy line from Cavallari hints at her current stance on money matters. She previously detailed her rocky relationship with Dennis and the unpaid loans during a July appearance on the Aspire with Emma Grede podcast. The Balancing in Heels author shared that she eventually came to terms with the financial loss. "I've had to grapple with it, you know, and I've ultimately put it to bed and made peace with it," she said. She admitted that at the time, she didn't know how to say no to her dad. That struggle became a big life lesson for her. In the end, she cut her dad out of her life entirely. "So I really figured out how to say no to him," Cavallari continued during the interview. But it was really hard for me when I was younger. And so, that's probably like the biggest thing that stands out in my mind in terms of how you think about teaching your kids about money.

In June 2025, Cavallari reflected on cutting ties with her father after claiming that he traumatized her children. "I always had a rough relationship with my dad," she said during an appearance on the Boyfriend Material podcast. He crossed the line with one of my boys, and that's a dealbreaker for me. Especially when he had zero accountability, no apology. Like, he traumatized my kids, and I have no room for that in my life. And so, that was it, she continued without detailing what took place. Cavallari said she hasn't spoken to her father in roughly three years. According to The Hills star, her father never tried to make amends after crossing the line with her son. To be honest with you, as a mom, if I had a kid, and I really f----- up with my kid, and they wanted to cut me out of their life, I would do everything imaginable to not let that happen. I would be like I am so f------ sorry, showing up at your house, like doing everything imaginable. And my dad, in a lot of ways, was like OK.