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Though they've gone down very different paths since their split, for a fleeting moment in music, Simpson and Wentz were the King and Queen of Emo.
They had a ton of mutual friends who they reportedly hit the clubs with pretty regularly, but that summer, sparks began to fly.
Alas, things between Wentz and Simpson were not meant to be: Just three years later, the "Pieces of Me" filed for divorce on February 9, 2011, citing irreconcilable differences.
Since then, the two have forged ahead in their own careers and personal lives: In 2014, Simpson wed actor Evan Ross. In 2014, Wentz and his current girlfriend, Meagan Camper, had a son, and in January 2018, the rocker announced that they are expecting another child together.
It looks like Ashlee Simpson found the person to give all the pieces of herself to!
Simpson and her hubby Evan Ross have been married for four years and have an adorable two-year-old daughter together.