Lindsay Lohan, Aaron Carter, Hilary Duff
When: December 2000 - July 2003
At the turn of the millennium, Aaron Carter was the young heartbreaker teenage boys hated but secretly wanted to be. "I started dating Hilary [Duff] on my 13th birthday," Carter boasted on The Big Idea with Donny Deutsch. "I was dating her for like a year-and-a-half and then I just got a little bored so I went and I started getting to know Lindsay [Lohan], dating Lindsay." But his fling with LiLo was a temporary look, as he dumped the rising starlet to give it another go with Hilary Duff. However, the multi-platinum pop sensation's wandering eye got the best of him and he ended up cheating on Duff with her best friend. Oh, Aaron!