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Kristin Cavallari opened up about her dynamic with her dad, Dennis Cavallari, in her 20s.
Kristin, 39, opened up about her finances in the beginning of her career while chatting with Good American cofounder Emma Grede during an episode of her “Aspire” podcast. During the episode, Grede, 43, asked her how she navigated having a larger bank account than the average 20-year-old, which Kristin quickly corrected, sharing that she lent her now estranged dad quite a large amount.
“I leant my dad money — I mean, hundreds of thousands of dollars in my early 20s that I’ll never see,” she claimed. “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.”
The Hills alum continued, “As a parent now, I can’t imagine asking my kids for money — especially that amount of money and putting that on them. I think at the time I didn’t know how to say no to my dad.” She went on to say that establishing a boundary with her father was “a big life lesson” for her. “I’ve ultimately cut my dad out of my life so I figured out how to say no to him. It was really hard for me when I was younger.”
This isn’t the first time Kristin has been candid about her relationship with her dad. In June 2025, she opened up about cutting ties with her father after he “crossed the boundary” with her three children, Camden, 13, Jaxon, 11, and Saylor, 10, whom she shares with ex-husband Jay Cutler.
“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 shared. “Such a weight has been lifted from me.”
She added, “There’s not one day where I miss him. … He crossed the boundary with my kids [and] couldn’t even apologize.”
Kristin continued, “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.”
Kristin Cavallari is discovering that her podcast tour will inevitably include a lot of highs and some emotional lows. During the Wednesday, June 11, episode of Honestly Cavallari: The Headline Tour, Kristin, 38, was visibly upset after some of her exes made awkward comments during her shows. “For me, it’s so triggering because every guy […]
In June 2025, Kristin told Harry Jowsey during an episode of his “Boyfriend Material” podcast that she hasn’t spoken to Dennis in “three years.”
“I always had a rough relationship with my dad,” she explained, noting that he “traumatized” her kids.
She added, “As a mom, if I had a kid and I was really f***ed 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***ing sorry.’ Showing up at your house, doing everything imaginable and my dad in a lot of ways was like, ‘OK.’ Like, he hasn’t tried.”
