If you mixed Ferris Bueller with Larry David and Alvy Singer (Woody Allen in "Annie Hall"), you'd get Sam Baum (Josh Gad). Sam's a lovable, quirky, neurotic NY native, emerging filmmaker, living in LA with his beautiful, compassionate, smart, and seemingly perfect aspiring actress girlfriend, Sammy (Kristen Ruhlin). Sam knows how lucky he is to have her in his life, since she was previously married to John (Johnny Messner): a, tall, fit, dashing, extremely successful surgeon and Harvard med school graduate, who she's remained cordial with. Before Sammy, Sam hasn't had much success romantically, so he overcompensates by routinely going out of his way to please her. He even offers her the female lead role in his next project... the night before one of Hollywood's hottest, most in demand actresses, Kim Powers (Hilary Duff), expresses interest in playing the role. Now Sam's caught in a pickle...