The career of screenwriter Dalton Trumbo is halted by a witch hunt in the late 1940s when he defies the anti-communist HUAC committee and is blacklisted.

In exchange for his freedom, charming con artist Neal Caffrey provides his expertise to help straight-man FBI agent Peter Burke catch elusive white-collar criminals.

Charlie Brandis leads a quiet and uneventful life as a wallflower. His parents trust him, his friends like him, girls are indifferent toward him. Then there's the girl he's watched from afar, Annie Briggs, who doesn't even know he exists. Until today. For today, the powers of fate conspire against him when jock friend Gary decides to throw a party at Charlie's house because the Brandis parents are away; a party specifically orchestrated to do one thing, put Charlie and Annie (who is unaware of this plan) together. The wrench comes in the form of Gary's older sister Margot, a girl who Charlie has also loved from afar, and who might be interested in him as well. The question is, when will Charlie stop doing things because other people want him to and take stock in his own situation.