When: 2002
Usher is said to have dated Puerto Rican singer Melinda Santiago in 2002 while she was signed to his production company and he was still with Chilli. She was also said to have gotten Usher's name tattooed on her hip, which scared away Tyrese when he tried to hook up with her. It apparently didn't scare away Teddy Riley, though, who not only married Santiago (and divorced her shortly thereafter), but met her on Myspace. To which we say...nothing. We just shake our heads sadly.
Smash Probability: