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Engaged: Less than three months
Naya Rivera was engaged to Big Sean in October 2013 but the musician reportedly ended the engagement in April 2014. Three months later, Naya married her longtime friend Ryan Dorsey in Cabo San Lucas, Mexico. And on Feb. 24, 2015, the Glee star announced that she was expecting her first child with Ryan. Their son Josey was born that September, but the couple called it quits a year later.