Sean Penn and Charlize Theron
In December 2013, after the end of his 16-year marriage to House of Cards star Robin Wright, Sean Penn began dating Charlize Theron. They dated for a year and then got engaged. But a few months after that they called it quits. According to the Mad Max star, the relationship just “didn’t work anymore.” Theron has two adopted children as a single mom. Penn has two children with his ex-wife Robin Wright.