Kristin Cavallari on Lending Dad Hundreds of Thousands: The Money She'll Never See

Learning to say no might be one of life’s toughest lessons, especially when family’s on the other end of the ask. Kristin Cavallari just opened up about a painful chapter from her early 20s that taught her exactly that — and it came with a price tag of hundreds of thousands of dollars.

During a recent episode of her“Aspire”podcast with Good American cofounder Emma Grede, the 39-year-old Hills alum got candid about her finances back when she was building her career. When Grede asked how she handled having a larger bank account than most people her age, Cavallari didn’t dodge the question. Instead, she revealed that she’d lent her dad, Dennis Cavallari, a staggering amount of money — funds she now knows she’ll never recover.“I leant my dad money — I mean, hundreds of thousands of dollars in my early 20s that I’ll never see,”she admitted.“Is it fine? I don’t know. It is what it is. I’ve had to grapple with it and ultimately put it to bed and make peace with it.”

What makes the story hit harder is Cavallari’s perspective now as a parent herself. She shares three children with ex-husband Jay Cutler — Camden, 13, Jaxon, 11, and Saylor, 10 — and the thought of asking them for money, let alone that magnitude, feels unimaginable to her. She pinpointed the real issue: she simply didn’t know how to set boundaries with her father.“As a parent now, I can’t imagine asking my kids for money — especially that amount of money and putting that on them,”she shared.“I think at the time I didn’t know how to say no to my dad.”

But the relationship deteriorated far beyond financial strain. In June 2025, Cavallari revealed that she’d completely cut her father out of her life after he“crossed the boundary”with her children and wouldn’t even apologize for it. She’s been transparent about how liberating that decision has been.“I mean, honestly, and this might sound messed up to some people, but it’s the best decision I’ve ever made, cutting my dad out of my life,”she said.“Such a weight has been lifted from me.”She later told Harry Jowsey on his“Boyfriend Material”podcast that she hasn’t spoken to Dennis in three years — a period she described as trauma-free in comparison to her earlier years.

What’s striking about Cavallari’s story isn’t just the money or the estrangement; it’s her refusal to let guilt keep her tethered to someone who hurt her. She’s clear-eyed about the reality:“If someone’s not bringing you joy, if people are only bringing you hurt and sadness and anger, what is the point? Even if it’s a parent, life’s too short.”That’s the kind of boundary work that doesn’t happen overnight, and the hundreds of thousands she lent her dad became the tuition for learning it.