When: 2001-2003
Usher and Chilli began a relationship in 2001, and kept it so quiet that we didn't know much about it until after they broke up. Usher opened up about the relationship in 2004, telling Vibe that they'd had a hot-and-cold relationship. First, he claimed, he'd wanted to stop everything he was doing and be with her—but later went on to tell her, "Get the fuck out of my house." In the same story, Usher attributed their breakup to Chilli's desire to get married and his own cold feet. We'd love to believe him, but right after their split, he dropped an album called Confessions (maybe you've heard of it?), on which he pretty much confessed to cheating on her.
Smash Probability: