Hilary Duffhas kept mostly mum about her strained relationship with her father, Robert "Bob" Duff, in recent years, but the 38-year-old is now opening up about their "challenging" dynamic amid the release of her new album, luck… or something, including her song "The Optimist," which is a nod to their family drama.
"I think it's really challenging for one person to have major success in a family," she said in a Feb. 20 interview with CBS News while discussing the song, which includes lyrics like "I wish I could sleep on planes/And that my father would really love me," and "He'd show up on my wedding day/He'd tell me how he wish he'd stayed/And that he never meant to disappoint me."
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"In 'The Optimist,' that's what it feels like for me," she continued. "And I'm sure it has to feel like that for him. Although I'm the kid. And it's been hard to get back to a place of health."
One day earlier, she revealed to Rolling Stone that there have been ups and downs in the relationship, including "times where I talk to my dad and times where I don't talk to my dad."
"A lot of s--- has gone down, and that’s life," she added.
Hilary Duff with Her Parents, Dad Robert Duff and Mom Susan DuffGetty
Bob himself has confirmed that Hilary's fame put a lot of strain on not just his relationship with the girls, but his relationship with his wife, Hilary and sister Haylie Duff's mom, Susan Duff, whom he divorced in 2008 following an extramarital affair he admitted to in an interview with Inside Edition.
"Susan was very consumed with the girls' careers… We simply grew apart," he told the outlet at the time. "I was unfaithful to our marriage. I feel very badly about that and the effect that it had on the girls."
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Duff sang about the betrayal in several songs off her 2007 album, Dignity, and it seems the father-daughter duo still struggles to reconcile fully to this day.
"Just because you’re born into a family doesn’t mean that it always stays together. You can only control your side and your street," she told Glamour recently. “I’ve had a very complicated life, and my parents had a very complicated thing."
Who Is Hilary Duff's Father, Bob Duff?
Though he mostly stays out of the spotlight, Duff's father, Bob, is a success in his own right. Long before Duff rose to fame as the star of Lizzie McGuire or a pop princess, Bob was already a millionaire as the owner of a chain of successful convenience stores.
However, he got himself into hot water in 2008, even spending a night in jail, after getting arrested for violating an injunction against selling assets without court approval. "I have never been handcuffed before," he told Inside Edition at the time.
Duff's new album luck... or something was released on Friday, Feb. 20, followed by her Lucky Me Tour later in 2026.
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