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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 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. 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 neighbourhood 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.
