Charlie seeks Dylan's help when he has a crush on a girl, but Dylan's rap music-informed advice clashes with Rebecca's more feminist take on how Charlie should handle the situation.

Charlie is tempted to change his clean reputation when a group of school vandals invites him into their clique, forcing Dylan to try to change Charlie's mind; Rebecca and Bethany protest when they are not allowed on the football team.

Hoping to be a baller in his latest music video, Dylan secures a credit card and starts ordering everything he needs to look the part, but after getting Rebecca and Charlie on board, the kids learn that credit card debt has to be paid back.