Not-too-popular high schooler, Rick Stevens (Wolff), tempts fate and worse by betting that he can bed the girl of his dreams, Nina Pennington (Gomez), before Arbor Day. But since Nina barely acknowledges Ricks existence, Ricks chances to win the are slim-to-none. So Rick schemes to win her over by securing backstage passes for them to meet her crush, music icon Josh Groban. Ricks seemingly sure-fire plans quickly fall apart, so he plots some Risky Business, with numerous complications that ensue involving an ever-growing list for Rick of classmates and co-conspirators, including the neighborhood priest (Lee); local mafia; Ricks strip-club-owner boss (McDermott); a phalanx of law enforcement; his best friends oversexed mom (Shue); one scintillating mob-owned attorney (Graham); and Ricks suicidal mother and his very own personal saint (Parker, in both roles) all helping Rick to prove, if nothing else, that loveor, at least, a teens hormonal attempts to get someknows no bounds.