Charles convinces Ellen to allow Adam to stay up and watch television all night, let Jamie streak her hair and allow Sarah to go on her first unchaperoned date. After one scary movie Adam ends up hiding in the closet, Jamie's hair turns out orange, blue and wild, and Sarah chooses to go out with the same shady character who sold Charles and Buddy overpriced tickets to an important playoff game. Concerned that Sarah will fall prey to this fast-talking boy, Charles and Buddy disrupt the movie theater where Gary (Scott Grimes) and Sarah are on their date, with their hilariously clumsy spying attempts. When a peeved Sarah assures Charles that her date is a gentleman, Charles has a heart-to-heart with him about the value of friends and the importance of "being yourself." Much to Charles' relief, Gary becomes likable, Adam comes out of his hiding place and Jamie fixes her hair.