Avril Lavigne, 21
It was a match made in pop punk heaven! Avril Lavigne was 21 when she got engaged to childhood friend and Sum 41 frontman Deryck Whibley in June 2005. The couple got hitched in July 2006 in Montecito, CA. Despite the couple being a perfect match on the music charts, their marriage did not last, and they officially divorced in November 2010. Avril went on to marry Nickelback frontman, Chad Kroeger, in July 2013.