After Jake discovers that Priscilla is now dating peculiar Les Riley Smith just to spite him, one of Jake's friends, Austin Eric Christian Olsen , suggests seeking retribution by turning Janey Briggs Chyler Leigh , a "uniquely rebellious girl", into the prom queen. Jake attempts to court Janey's love, but faces adversity from his own sister, Catherine Mia Kirshner , who is sexually attracted to him; Janey's unnoticed admirer and best friend, Ricky Lipman Eric Jungmann ; and memories from his past football career. Catherine eventually assists her brother by slightly altering Janey's appearance by simply removing her glasses and ponytail , instantly making her drop dead gorgeous. Meanwhile, Janey's younger brother, Mitch Cody McMains , and his friends, Ox Sam Huntington and Bruce Samm Levine , make a pact to lose their virginity by graduation despite still being in their freshman year. Mitch tries to impress his longtime crush, the beautiful yet perverted Amanda Becker Lacey Chabert with a letter professing his love for her.