36. Mandy Moore and Ryan Adams
The bubbly teen star fell in love with a grungy, alternative rocker, Ryan Adams. Most of his pictures online feature him covered in sweat and grease, in desperate need of washing his hair. If you didn’t know it, you’d think he was just another hipster in Austin begging you for change. Mandy Moore grew from teen stunner to red carpet queen, but he’s just the same grungry boy. The two began dating in 2008, and married in 2010. They made it just five years, divorcing in 2015.