Kristin Cavallari is reflecting on a painful lesson after lending her father a quarter of a million dollars.
During a recent episode of her podcast “Let’s Be Honest with Kristin Cavallari,” in which the 39-year-old reality star shared her opinions on women and finances, Cavallari recalled how she ended up $250,000 “in the hole” following two loans to her father Dennis Cavallari that were never repaid.
“My dad came to me — I was filming ‘The Hills,’ so I must have been 22 — and asked for a large sum of money to borrow. Six figures,” she said.
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“And I was making great money at the time, but it’s still — I’m 22,” Cavallari continued. “Six figures is a big deal for me.”
“But I lent it to him, and he promised me he would pay me back,” the Uncommon James founder remembered. “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. And instead, he asked to borrow more money, another six-figure number.”
Cavallari said that she confronted Dennis about not repaying the 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.”
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The “Laguna Beach” alum admitted she has no expectation of ever getting the money back.
“I will never see that money,” she said. “So, when I tell you, I’m in the hole with my own dad, a quarter of a million dollars.”
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“Talk about a bad business decision,” Cavallari added.
However, the TV personality acknowledged that the experience taught her the importance of setting boundaries with family and friends when it comes to money.
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“I didn’t know how to set boundaries in my early 20s,” she admitted. “I’ve learned that. You know, it would be a very different conversation probably today, but it’s the lending-money-to-people thing.”
“When you have money, it’s almost like people expect it,” Cavallari continued. “And 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.”
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“Like I have worked my ass off for all of my money,” she added. “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.”
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Now a mother herself, Cavallari said she struggles to understand her father’s decision to turn to her for such a large sum of money when she was so young.
Cavallari shares sons Camden, 14, and Jaxon, 12, and daughter Saylor, 10, with her ex-husband, former NFL quarterback Jay Cutler.
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“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,” Cavallari continued. “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. “I’m over money being a taboo topic for women. We’re 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.”
Cavallari previously discussed her difficult 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. “I think at the time, I didn’t know how to say no to my dad. That’s also been sort of like a big life lesson for me. I mean, I’ve ultimately cut my dad out of my life.”
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“So I really figured out how to say no to him,” Cavallari continued. “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.
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“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.
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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.’”