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Did She Really Date Him?: Brody Jenner and Avril Lavigne
Brody Jenner and Avril Lavigne

This surprising pair started dating in 2009 after the singer filed for divorce from her first husband, Sum 41 singer Deryck Whibley. They split after nearly two years together but have remained friends. Jenner even wished Lavigne the best of luck in her most recent marriage to Chad Kroeger. Photo: Andrew Evans / PR Photos.