Ronald Miller is a typical high school nerd living in suburban Tucson, Arizona. He has spent all summer mowing lawns to save up for a telescope. At an opportune moment, he makes a deal with next-door neighbor and popular cheerleader Cynthia "Cindy" Mancini. Cindy had borrowed her mother's expensive suede outfit without permission, to wear to a party, only to have Quint accidentally spill red wine on it. Cindy reluctantly agrees to help Ronald look "cool" by pretending to be his girlfriend for a month for $1000, even though she already has a boyfriend named Bobby who is attending the University of Iowa.