When: 2000-2001 & 2004
One of the chapters in Steffans' book Confessions of A Video Vixen, "Ushering In," detailed the supergroupie's sexual encounters with Usher. She claimed that they first started dating smashy-smashing in 2000, but slowly stopped once Usher started dating Chilli. She also claimed that they had another five-month affair in '04, but it ended once Usher hit it in a hotel room, treated her like shit afterward, and then went to the room next door to smash another chick. Sure, that was grimy of Usher, but at least he didn't try to play Captain Save-a-Hoteljumpoff.
Smash Probability: