Picture 12 of 13
Picture 12 of 13

Usher really could of had it all when he was with TLC member Chilli, but due to his immaturity, it was inevitable that their relationship would come to an end. Even though he found love and had two sons with Tameka Foster, we could always tell the love was a bit distant. Now that Usher is divorced, it looks like he's waiting patiently for it to come his way again.