Kristin Cavallari says a painful financial decision involving her father left her $250,000 in the hole and taught her a lasting lesson about money, trust, and boundaries. The reality star revisited the experience during an episode of her podcast, “Let’s Be Honest with Kristin Cavallari.”
As Fox News reported [1], Cavallari, 39, said her father, Dennis Cavallari, approached her for money while she was filming “The Hills.” She was around 22 at the time and earning what she described as great money, but the requested amount was still significant to her.
“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. Her father promised to repay her, possibly within six months, and offered interest on top of the loan.
The repayment never came, according to Cavallari. Instead, Dennis returned with another request for an additional six-figure amount, even though he had not acknowledged or repaid the first loan.
Cavallari confronted him about the unpaid money but ultimately agreed to provide the second loan. She recalled telling him, “You haven’t even acknowledged the first payment, and now you want more money?”
Despite that concern, she handed over more money. “But because I’m such a f—–g sucker — or I was at the time — I lent him more money,” Cavallari said.
The “Laguna Beach” alum now believes she will never recover either loan. “I will never see that money,” she said, explaining that the two transactions left her down a quarter of a million dollars.
“Talk about a bad business decision,” Cavallari added. Yet the Uncommon James founder said the experience ultimately showed her why firm financial boundaries are necessary, even when requests come from relatives or friends.
Cavallari acknowledged that she did not know how to establish those limits during her early 20s. She said the conversation would probably unfold very differently today because she no longer believes having money makes someone obligated to lend it.
“When you have money, it’s almost like people expect it,” she said. “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.”
Cavallari said she had worked hard for everything she earned, which made the loss especially painful. She felt her father had taken advantage of her when she was young and still learning how to say no.
Now a mother, Cavallari said she cannot imagine making the same request of her own children when they reach 22. She shares sons Camden, 14, and Jaxon, 12, and daughter Saylor, 10, with her former husband, former NFL quarterback Jay Cutler.
She acknowledged that her father may not have had many options but said their relationship contains other complicated layers. Cavallari emphasized that people are entitled to decide for themselves what they do with their money.
The television personality also promoted the podcast episode on Instagram as a broader conversation about financial literacy for women. She said the discussion covered financial independence, her mistakes and the lessons she learned, while rejecting the idea that money should remain a taboo subject for women.
Cavallari previously discussed the unpaid loans during a July appearance on the “Aspire with Emma Grede” podcast. She said she had wrestled with the loss before eventually accepting it and making peace with what happened.
“I think at the time, I didn’t know how to say no to my dad,” she said during that appearance. Cavallari described learning to refuse him as a major life lesson and said she ultimately cut him out of her life.
In June 2025, Cavallari addressed that estrangement during an appearance on the “Boyfriend Material” podcast. She said she had always experienced a difficult relationship with her father and claimed he crossed a line with one of her sons and traumatized her children.
Cavallari said her father showed no accountability and offered no apology after the incident, which she did not describe in detail. She also said she had not spoken to him in roughly three years and that he never attempted to repair the relationship after crossing that line.