Jul 03 2014 Usher Is Photo’d Out With His COUGAR GIRLFRIEND . . . And She Looks A LOT YOUNGER . . . Than 45 Years OLD!!! July 3, 2014: Usher’s girlfriend Grace is 45 years old . . . but she looks GREAT for her age. Usher has made it KNOWN in that past that he prefers OLDER women, and Grace definitely fits the bill. The pair have been dating now for almost 2 years.