Kristin Cavallari Recalls Giving Her Estranged Dad Money: Couldn’t ‘Say No’

Kristin Cavallari has opened up about her financial history with her estranged father, Dennis Cavallari, revealing she lent him "hundreds of thousands of dollars" in her early 20s that she will never see again. During an episode of her "Aspire" podcast, she told guest Emma Grede that as a parent now, she can't imagine asking her children for that amount of money. She said she didn't know how to say no to her dad at the time, but that establishing that boundary was a "big life lesson." This is not the first time Kristin has discussed her difficult relationship with her father. In June 2025, she shared that she cut him out of her life after he "crossed the boundary" with her three children, calling it the best decision she's ever made. She added that her father hasn't tried to reconcile, stating that if someone is only bringing hurt and sadness, there is no point in keeping them in your life, even if it's a parent.