Avril Lavigne – 2009

Lavigne started singing at a young age, and became famous upon her first album, “Let Go.” In 2009, after years of marriage to Deryck Whibley, the lead singer of the band Sum 41, she filed for divorce. She later went on to date both Brody Jenner and Chad Kroeger.

However, she reportedly dated Wilmer before those two, right after her separation from Whibley. They became friends after working together on the documentary “Fast Food Nation,” and apparently things got serious thereafter.