When his doctor says he has to take better care of himself by eating healthier and exercising, Uncle Phil is less than thrilled at that prospect. As a result, he has Will sneak into the mansion unhealthy food from various fast food joints and ultimately has a heart attack. While Uncle Phil is recovering in the hospital, Will tries to convince a scared Carlton to visit his father.

When Jackie finally agrees to go on a date with Will, he reluctantly has to cancel when Hilary asks him to be her chaperone at the Playboy Mansion, where she is asked to pose in an upcoming issue. Upon learning of Hilary's opportunity, Uncle Phil forbids her from posing for the magazine. However, when he learns that she decides to go with it, Uncle Phil decides to go into hiding.

It's Halloween and Hilary decides to hold a séance with a somewhat well-known psychic in order to say goodbye to Trevor and forces the family to go with her. However, when Will begins to mock the psychic, he puts a curse on him, resulting in everyone else at the mansion having bad luck. Will then goes back to the psychic's house and begs him to lift the curse.

With Aunt Vivian out of town and unable to play mediator between Will, Carlton, and Uncle Phil. The guys promptly get into a little tiff when Uncle Phil hears about a party the boys want to host at the pool house. When Will and Carlton refuse to pay their rent until Uncle Phil fixes their air conditioning, Uncle Phil gets the last laugh when he takes the boys to court.