In the stereotypical high school community of John Hughes High in Southern California, Priscilla, head cheerleader, separates from her football star/slacker boyfriend, Jake Wyler. Discovering she is now dating timid and weird Les to spite him, one of Jake’s friends, Austin, makes a bet with him to turn nerdy Janey Briggs into the prom queen. Janey is not insecure enough to feel any need to change herself, nor does she feel anything for him at first, but that does not stop him from trying. As Jake attempts to court Janey, he faces adversity from his own sister, Catherine, who is sexually attracted to him; Janey’s unnoticed admirer and best friend, Ricky Lipman; and memories from his past football career.