When: 1997
Usher became a superstar with his multi-platinum album My Way—and around the same time, he also began a recurring role on the UPN sitcom Moesha as the boyfriend of the title character (played by Ms. Norwood). So you can see why rumors about these two hooking up would start flying. Both denied being romantically involved, with Usher telling Jet, "We're just friends. We have to keep a friendship going to keep a healthy look on camera...I'm a single man, but I have friends." They can deny all they want, but you can't deny that they look adorable in that picture. AWWWWW.
Smash Probability: