When Julius and Rochelle have a special 'date night' they hire a baby-sitter. But Chris is called upon to take charge when she leaves to take care of something personal.

After Julius' truck is stolen Rochelle decides to get involved with a neighborhood watch group, but instead ends up in a competition with new neighbor Louise (Whoopi Goldberg). Chris asks out a new girl in the neighborhood hoping not to get rejected again. Drew has the girls all over him when he volunteers to be a crossing guard.

The new principal, Mr. Edwards, decides that the best way to solve the issues between Chris and Caruso is to have them become buddies on a school field trip. When Rochelle's favorite earrings are missing Tanya is the prime suspect. Julius tries to find a Wayne Gretzky jersey for Drew.

Rochelle decides to help tutor Chris for a math competition in algebra, when Chris doesn't think she's helping he turns to his grandmother Maxine for help. Tonya blackmails Drew when she takes the blame for breaking Julius' favorite chair for Drew.

Chris' attempt to be a "cool" kid lands him in hot water when he is caught with cigarettes and is suspended from school. Kicking him while he's down, Tonya blackmails him when she finds out before their parents do. Meanwhile, Rochelle decides to teach Julius a lesson.

When Chris becomes the only boy in school without a date for the ninth-grade dance, Ms. Morello suggests he ask the only girl without a date, and she accepts. But trouble ensues when word gets out about the inter-racial pairing. Meanwhile, Tonya stresses her parents out about ballet classes.

Coach Thurman spots Caruso bullying Chris and suggests he take up boxing to defend himself. Meanwhile, Julius has a new set of problems when he suspects Rochelle of adultery and catches the eye of a female neighbor...