Who could forget the odd coupling of Hilary Duff and Joel Madden — the good girl Disney star paired with the punk rocker from Good Charlotte.
And in a new interview with the actress, the 27-year-old hints that she lost her virginity to the older musician.
“I had a 26-year-old boyfriend,” Hilary tells 'Cosmo' of Joel, whom she began dating at age 16. “So everyone can make their own assumptions about what I was doing.”
Hilary and Joel in 2006. (Photo Credit: Getty Images)
Throughout the pair's two-year relationship, their nine-year age difference was often scrutinized, though Hilary admits she wasn't always the squeaky-clean teen she was made out to be in the press.
"I've enjoyed myself," she reveals to 'Cosmo.' "I think everyone should have something where you know it's not exactly what you're looking for but you just have a wicked good time. That was really freeing for me and a bit of an awakening. It's fun to have a secret."
Hilary with former hubby Mike Comrie & Joel with wife Nicole Richie. (Photo Credit: Getty Images (2))
Since their split, both Hilary and Joel have moved on. The actress married hockey player, Mike Comrie, with whom she shares a 3-year-old son, but recently filed for divorce — while Joel married Nicole Richie in late 2010 and welcomed two children.