a lovable, quirky, neurotic NY native, living in LA with his beautiful girlfriend, Sammy(Kristen Ruhlin). A girl he knows how lucky he is to have in his life, since she was previously married to John: a, tall, fit, gorgeous, extremely successful Harvard med school graduate, who she's remained cordial with. Before Sammy, Sam hasn't had much success, romantically. He's an emerging filmmaker with one feature film under his belt that nobody's heard of. And she's an aspiring actress, inching for her big break, which may never come, unless Sam offers her the female lead in his next project, which he does... the night before one of the hottest, most in demand actresses working today, Kim Powers(Hilary Duff), expresses interest in playing the role. Sam wears his heart on his sleeve and has always been honest with Sammy, but now he's caught in a pickle...

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