<P> Ronald Miller ( Patrick Dempsey ) 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 ( Amanda Peterson ) . Cindy had borrowed an expensive suede outfit belonging to her mother ( Sharon Farrell ) , without her permission , to wear to an end - of - the - summer / back - to - school party , and needs to replace it quickly after Quint ( Cort McCown ) accidentally spilled red wine on it at the party . Having few options , save for telling her mother the truth , Cindy reluctantly agrees to Ronald 's proposal : he will give her $1000 to purchase a new suede outfit , and she will help him look `` cool '' by pretending to be his girlfriend for a month , even though she already has a boyfriend named Bobby ( George Gray ) who is away at his freshman year at the University of Iowa . Ronald feels that he can be a part of the popular crowd if they think Cindy is dating him . Both agree never to reveal their financial arrangement . </P>
<P> Ronald Miller ( Patrick Dempsey ) 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 ( Amanda Peterson ) . Cindy had borrowed an expensive suede outfit belonging to her mother ( Sharon Farrell ) , without her permission , to wear to an end - of - the - summer / back - to - school party , and needs to replace it quickly after Quint ( Cort McCown ) accidentally spilled red wine on it at the party . Having few options , save for telling her mother the truth , Cindy reluctantly agrees to Ronald 's proposal : he will give her $1000 to purchase a new suede outfit , and she will help him look `` cool '' by pretending to be his girlfriend for a month , even though she already has a boyfriend named Bobby ( George Gray ) who is away at his freshman year at the University of Iowa . Ronald feels that he can be a part of the popular crowd if they think Cindy is dating him . Both agree never to reveal their financial arrangement . </P>
who played bobby in ca n 't buy me love
who played bobby in ca n 't buy me love
George Gray
George Gray