They weren’t married but their split-up is just as heartbreaking to the tween community as the breakups of Brad and Gwyneth and Brad and Jennifer were to us stunted adults. Good Charlotte’s frontman Joel Madden has been telling fans that the eight-year age difference between him and pop princess Hilary Duff eventually led to her dumping him almost two weeks ago. (The Bosh)

19-year-old Duff and 27-year-old Madden had been dating for a little over a year. The pair were reluctant to make their romance public at first due to the fact that Hilary was still a minor when they began seeing each other.