Chris Brown and Rihanna
Their relationship used to be an ideal one and then it took an ugly turn after a 2009 pre-Grammys Awards party, and “ugly turn” is an actually understatement, because Chris badly beat Rihanna, leaving her with a bleeding face. Chris was charged for assault later and got felony probation. Still, both continued dating through 2012 and 2013. Rihanna believed that she could be his “guardian angel” and resolve his issues. The two collaborated for music and shared some PDA moments as well. And then, they ultimately couldn’t take it further, making their ways separate in the end. A matured decision it was!