Hilary was just 16 years old when she started dating Joel (who was 25). They made it last for 2 years, but it ultimately didn’t work out.
In July 2004, a 16-year-old Duff began dating Good Charlotte singer Joel Madden, who was then 25 years old. After a long period of tabloid speculation, Duff's mother Susan announced their relationship in a June 2005 interview for Seventeen magazine. Madden worked with Duff on her compilation album, Most Wanted. In November 2006, Duff and Madden broke up.