Hilary Duff & Mike Comrie

Hilary Duff rose to fame as part of Disney, while Mike Comrie has made a name for himself as a professional hockey player. Their relationship was fast-paced since it started in 2007. They got engaged and then married in 2010. Many thought that theirs was a perfect marriage, but things got a bit rocky after their nuptials. They welcomed their son in 2012 but put a halt to their marriage in 2013. They separated for two years until a scandal broke out.

Duff wanted full custody of their son, Luca, but they were given joint custody instead. The Lizzie Mcguire star stated that they were just too young when they got married, contributing to their dissolution. To their credit, they co-parented their son and remained friends even today. They were even spotted giving each other a goodbye kiss which only shows that they remained close even after all the drama.