Hilary Duff Has A Concerning Age-Gap Relationship In Her Past

Age-gap relationships aren't uncommon, especially in Hollywood, but some couples still shock us when we realize how wide the age gap that separates them is. Hilary Duff is married to Matthew Koma, and they are the same age, but throughout her past relationships, Duff hasn't always stuck with people who were the same age as her. In the early aughts, the actor and singer went through a concerning age-gap relationship that would raise many red flags nowadays.

In 2004, millennials everywhere went crazy when they found out Duff was dating Joel Madden, the vocalist of the rock band Good Charlotte. At the time, Duff was 16, and Madden was 25. Despite the age gap — and Duff being underage — the relationship didn't raise as many eyebrows as it would today.  Duff has since hinted at how problematic it actually was. 

While talking to Vogue in 2025, she spoke about her song, "Mature." She said, "The song is about reflecting on your past and coming to terms with the choices you've made, but without being too hard on yourself." While she didn't name Madden, she added: "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."

In the interview, Duff also spoke about her song "Mature." Even though she hasn't explicitly stated that the lyrics are about Madden, she left enough clues for fans to speculate that there is a good chance that this is the relationship that Duff is alluding to.
 

Hilary Duff and Joel Madden's relationship ended in 2007. Back then, Joel Madden spoke to People and indicated that they parted on good terms and continued to have a good relationship. He stated: "People can say or think whatever they want ... so in my reality, it's kind of irrelevant. I'm always the kind of person that does the right thing and keeps my side of the street clean."

A lot of people seem to think that "Mature" is about Madden. While he hasn't addressed that, he did show support for it on Instagram. Madden's wife, Nicole Richie, posted a photo of her and Duff having a laugh-out-loud moment. Richie captioned it with (per New York Post): "'Mature' is not the word I'd use to describe us, but regardless, this song is a BOP." Madden didn't add his own commentary, but he did re-share the post. 

The song "Mature is on Duff's album, "Luck... or Something," which references some of the tragic details about her life. In a 2026 interview with Glamour, she revealed more about the relationship behind the song. "It was very brief with someone older than me, and that was not illegal, but inappropriate when you have this much time removed from it. ... But the one thing that I'll say is, working as an adult since I was 10 years old, it's very hard to have relationships with people your own age."