Raven tries to keep her distance from the boy Chelsea likes, but that proves difficult since the two are working together on a benefit concert.

Raven has almost given up on her dream of being named "best dressed" at school when her sweet, but not very chic, guidance counselor, Ms. Romano (Susan Lucci), offers some words of encouragement. To pay her back for the confidence boost, Raven treats Ms. Romano to some fashion pointers.