On the day of Maude's eightieth birthday, Harold proposes to her but he finds the truth about life at the end of hers.
Todd Anderson (Ethan Hawke), a lonely and painfully shy teenager, who is under pressure by his stern parents because he must live up to his older brother’s reputation to attend Yale and become a lawyer, arrives for the new semester at the Welton Academy for boys.
Marlon Wayans (Dungeons and Dragons) Shawn Wayans (Scary Movie) Jaime King (Sin City) Frankie Faison (The Silence of The Lambs) Lochlyn Munro (Freddy vs Jason) John Heard (The Lizzie Borden Chronicles) Busy Philipps (The Smokers) Terry Crews (Get Smart) Brittany Daniel (That 80S Show) Jennifer Carpenter (Limitless tv) Evangeline Lilly (Lost)The plot begins in a convenience store where two FBI agents and brothers, Kevin Copeland and Marcus Copeland (Shawn and Marlon Wayans), try to capture members of an organization that sells drugs inside ice cream boxes, posing as dominican clerks.
This semester begins during an orientation gathering with a speech given by the stern Headmaster Nolan (Norman Lloyd), who states the academy’s four pillars: Tradition, Honor, Discipline, and Excellence.
Todd meets Neil Perry (Robert Sean Leonard) an ambitious student whom becomes his dorm roommate.
John “where am I” Lydon shows an interest in the news reporter Brett Porter, but the affair becomes more and more complicated as the two agents must now repeatedly switch between their gender roles.
Marcus’ wife Gina, whose relationship is already troubled, becomes an additional complicating factor as she gets suspicious when she hears a woman’s voice in the background during a phone conversation with Marcus.
This leads to the chief finding out that Marcus and Kevin have been impersonating Brittany and Tiffany. Later on, Kevin and Marcus find out that due to his bankruptcy Mr. Marcus apologizes to Gina, after realizing that being a female is a hard task, and because he had been ignoring Gina for his job.
Vandergeld, along with Heath, has been behind the socialiate kidnappings in order to save himself and his family from poverty. Denise falls for Kevin, after Kevin saves her from a bullet.
A date with Marcus/Tiffany is then sold off to Latrell during a charity dinner.
Kevin takes advantage of the situation and asks Denise out on a date, pretending that he is Latrell, as Denise has a history of dating rich men.
At the Hamptons hotel, Kevin and Marcus meet Brittany and Tiffany’s three best friends, Karen, Tori and Lisa, and their rivals Megan and Heather Vandegeld.