Which two people make a bet?
Zack Siler is the big man on campus at his Southern California high school. His popular and narcissistic girlfriend, Taylor Vaughan, ditches him for a faded reality TV star from The Real World, Brock Hudson, whom she met on Spring Break in Florida. Although bitter over the break-up, Zack consoles himself by claiming that Taylor is replaceable by any girl in the school. Zack's friend, Dean Sampson, Jr., disagrees and challenges him to a bet on whether Zack can turn any random girl into the Prom Queen within six weeks, a coveted position held by the most popular girl in school. Dean picks out Laney Boggs, a dorky, solitary, unpopular art student, as his choice for Zack.
Zack approaches and attempts to befriend Laney in the hope of subsequently transforming her into prom queen material. His first encounter with her is a complete failure, when she pointedly ignores his advance and walks away from him. With help from Laney's friend, Jesse Jackson, Zack eventually is successful in getting Laney to take him to a theater lounge frequented by artists and performers. Intending to deter him, Laney arranges for Zack to be called onto the stage and perform to his surprise. Zack manages to improvise a show with the Hacky Sack he happens to carry in his pocket. Laney is impressed by the performance, but rejects him again after he attempts to charm her.
Zack Siler Dean Sampson, Jr.