Ronald Miller (Dempsey) is a typical high school nerd living in Tucson. He has spent all summer mowing lawns to save up for a telescope. At an opportune moment, he makes a deal with popular cheerleader Cynthia “Cindy” Mancini (Peterson). Cindy had borrowed a suede outfit that belonged to her mother, without her permission, and needs to replace it quickly after Quint (Cort McCown) accidentally spilled red wine on it at a party.