Ryan is a rude and immature 18 year old boy who still wears diapers at night to deal with his occasional bedwetting. When he gets suspended from school on the eve of his mother's trip out of town, she calls on Amy: a 26 year old corporate businesswoman and Ryan's former childhood babysitter. While Amy graciously agrees to look after Ryan, she quickly finds her charge to be dishonest, disobedient, and disrespectful. Despite being attracted to Amy, Ryan thinks she is strict, uptight, and downright bitchy. As Ryan pushes Amy to her limits, she becomes convinced that the only thing that can curb Ryan's behavior is a little strict discipline, even if it means resorting to some radical punishments. If Ryan insists on acting like a child, then Amy decides she is all to happy to treat him like one. Its an escalating battle of wills where only one can win. Amy quickly becomes determined to enforce her adult authority as Ryan's babysitter once and for all... and when she does, neither of them will ever be the same again.