At 16 years old, Hilary Duff began dating 25-year-old Good Charlotte’s frontman Joel Madden. The relationship spanned two year, with fans speculating that the age-gap inspired her recent single, “Mature.” Among many lyrics about a former partner and their new, younger girlfriend, Duff sings, “She looks like she could be your daughter, like me before I got smarter. When I was flattered to hear you say, ‘You’re so mature for your age, babe.’”
“Mature’ is a little conversation that my present self is having with my younger self,” Duff revealed in a press release, per People. “The two of us are reflecting on a past experience and sending love to each other. It’s a chuckle, a wink, and a sense of being grateful that we are sure footed in where we landed.”
Despite fan speculation about the somewhat scathing lyrics, Duff told Vogue it’s about a “brief experience” she had “a long, long time ago,” but that it’s“not totally autobiographical.” She continued, “I took a few artistic liberties just to make the song work structurally, but the gist is the gist. I was looking back on this relationship and thinking about whether this guy had a habit of dating younger women or whether I was ‘special.’ The whole experience was super therapeutic to write about, but being so vulnerable through your music can be really scary.”
Duff continues to maintain a strong, supportive friendship with Nicole Richie, who began dating Madden after his split from Duff in 2006. The pair have been married since 2010 and share two children.
Hilary Duff and Frankie Muniz (2002)
Muniz recently revealed he dated Hilary Duff for a brief period in 2002, but stopped speaking to his former costar immediately after shooting Agent Cody Banks. “I’ve never talked to Hillary since the last day of filming. I’ve not said one word to her since then,” Muniz said on the on the Joe Vulpis Podcast in October 2025, per E! News. “There was a small dating element at the time. So there was also that element that wasn’t happening anymore, so, it was awkward because of that.”