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Episode Number: 13 Season Num: 1
One day, Will needs the car to go to a concert with Jazz. But right before Philip says he can have it, Hilary starts mentioning things that get Will grounded for a month just so she can have the car instead of him. Will becomes determined on revenge. His chance comes when he overhears Hilary mention she lied to her parents about studying at the library. He goes to UCLA and talks to some of her friends. They tell him Hilary dropped out of school three months ago. At home, while the entire family is gathered, Will makes up a story about going to UCLA and sitting in Hilary's physics class. Hilary becomes alarmed and pulls him aside later to demand what he knows. Will tells her he knows everything. He also tells her that unless she wants her parents to find out, she would be his servant for the month she got him grounded for. After some time of working for Will, Hilary goes to Carlton and tells him the situation. She wants his help to get Will punished for his actions, but Carlton plays Will's game and also blackmails her. At dinner that night, Will and Carlton get Hilary to do hilarious things. Eventually, she can't take it anymore. She bursts into tears and screams that she dropped out of college three months ago. Her parents are very angry at her, and tell everyone to leave the room.
Later, Philip and Vivian find Will and Carlton and tell them that they are grounded for blackmailing Hilary. They find Hilary and apologize for what they did to her. They never would have guessed she would have broken down the way she did. Hilary forgives them and they tell her they never would have told her parents anyway.