Brody Jenner and Avril Lavigne
He: Son of Olympic gold medalist Bruce Jenner; stepbrother to the Kardashian sisters; starred on the MTV reality shows Princes of Malibu and The Hills; dated fellow reality stars Kristin Cavallari, Nicole Richie, and Lauren Conrad
She: Canadian singer-songwriter known for hits such as “Complicated” and “Sk8r Boi”; designer of the punk rock-inspired clothing line Abbey Dawn; ex-wife of Sum 41 lead singer and guitarist Deryck Whibley
Status: Brody and Avril began dating in February 2010, but broke up in early 2012. Though their affinity for hoodies and trucker hats once brought them back together, the two have officially gone their separate ways. Avril is now engaged to Nickelback frontman Chad Kroeger.