Synopsis:
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 Rick’s existence, Rick’s chances to win his bet 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. Rick’s 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; Rick’s strip-club-owner boss (McDermott); a phalanx of law enforcement; his best friend’s oversexed mom (Shue); one scintillating mob-owned attorney (Graham); and Rick’s suicidal mother and his very own personal saint (Parker, in both roles) – all helping Rick to prove, if nothing else, that love…or, at least, a teen’s hormonal attempts to ‘get some’…knows no bounds.