"Tom, Sarah and Usher" is the second episode of the second season and the seventeenth episode overall of The Boondocks. It originally aired on October 15, 2007. Sarah and Tom split after an unexpected appearance by Usher causes an infatuated Sarah to put on a girlish display at their anniversary dinner. Tom, chagrined, is kicked out of the house and attempts to learn assertiveness from A Pimp Named Slickback.