In order to get the family car instead of Will, Hilary tells Phil that Will has been disobeying curfew, subcontracting his chores to Ashley and renting out the family car. He is consequently grounded for a month. Will plans revenge; while going to find out where Hilary is shopping, he learns that she dropped out of college three months ago. Will uses this in order to get Hilary to slave for him during his punishment. Hilary tries to get Carlton to go against Will, but instead he blackmails her too. Carlton and Will both have lists of embarrassing tasks that Hilary must do at the dinner table. When this proves too much pressure for Hilary, she admits she dropped out. Her parents have a long talk with her about her path in life, but also come down on Will and Carlton for their blackmail, giving Will another month of confinement. In the end, Will admits to Hilary that he wasn't planning to tell her parents about dropping out of college as he was trying to teach her a lesson about ratting him out, which she gets and learned from it.

Will realizes that Ashley has never experienced a real Christmas before (since back in Philadelphia, there would be carolers, lights and neat decorations, while in Bel-Air there are only a few decorations, no carolers, and hardly anything in the Christmas spirit) and goes out of his way to let her have one. He decorates the inside of the house and also the outside with hundreds of lights, decor, and colors; upsetting some of the neighbors, to include Evander Holyfield.