14. Miley Cyrus and Liam Hemsworth (2009-2013)
Lesson: Never trust someone who sticks their tongue out
Miley Cyrus entered the biggest transition of her career yet in 2013 when she broke free from her pop-star image and became a music and fashion idol with her album Bangerz. But her on-again/off-again relationship with her first serious boyfriend, Hunger Games actor Liam Hemsworth, ended around the same time, breaking off their year-long engagement. Though their romantic relationship didn’t last, the couple says they will always remain friends.
