Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.
Patrick Dempsey
as Ronald Miller
Amanda Peterson
as Cindy Mancini
Courtney Gains
as Kenneth Wurman
Tina Caspary
as Barbara
Seth Green
as Chuckie Miller
Sharon Farrell
as Mrs. Mancini
Dennis Dugan
as David Miller
Darcy DeMoss
as Patty
Devin DeVasquez
as Iris
Eric Bruskotter
as Big John
Gerardo Mejía
as Ricky
Cort McCown
as Quint
