Kristin Cavallari says she lost $250,000 after lending money to her father in two transactions when she was about 22 and filming “The Hills.” Speaking on an episode of her podcast, “Let’s Be Honest with Kristin Cavallari,” she said the loans were never repaid and described the experience as a costly lesson in setting boundaries around money.
Cavallari said her father, Dennis Cavallari, first asked to borrow a six-figure sum. Although she was earning well at the time, she recalled that the amount felt substantial at her age. She said he promised repayment within about six months, with interest, but did not pay her back. He later asked her for another six-figure loan.
She said she questioned him about seeking more money without acknowledging the first unpaid loan, but agreed to lend again. Cavallari said she does not expect to recover the money and characterized the combined loss as a quarter of a million dollars. She called the decision a bad business move and said the experience felt particularly painful because she believed she had worked hard for her earnings.
The reality television personality said she had not learned how to establish boundaries in her early 20s. She said that having money does not obligate someone to lend it to others, including relatives, and that she would likely approach such a request differently now. Cavallari also said that, as a mother, she finds it difficult to imagine asking her own children for such a large amount when they are young adults.
She acknowledged that her father may have had few options, while also saying their relationship has other complications. Cavallari shares three children with former husband Jay Cutler: sons Camden and Jaxon, and daughter Saylor.
Cavallari has discussed the loans and her relationship with her father in earlier public appearances. In July, on the “Aspire with Emma Grede” podcast, she said she had come to terms with losing the money and described learning to say no to her father as a significant life lesson. She also said she had ultimately cut him out of her life.
In June 2025, Cavallari said on the “Boyfriend Material” podcast that she ended contact after an incident involving one of her sons. She described the situation as a dealbreaker and said her father had not apologized or taken accountability, but did not provide details about what happened. She said at that time that she had not spoken with him for roughly three years.
Cavallari shared a clip from the recent podcast episode on Instagram, where she said the discussion covered financial independence, mistakes she had made, and what she had learned. She framed the episode as part of a broader effort to make conversations about money less taboo for women.
