Dean's plans to ask Keisa to the Valentine's Day Dance are foiled when another boy asks her out first after a new makeover makes her the talk of the school. Meanwhile, Bill and Lillian make Kim sign up for a Big Sister program to have extracurricular activities for her college applications.

When their teacher goes on maternity leave, Dean, Cory and Keisa are excited to be taught by Mr. Brady, the school's first Black teacher. Mr. Brady encourages the students to try out for the Knowledge Bowl team where Dean faces some unexpected challenges.