Herman Spooner (Matthew Lillard) is a used car salesman who still lives at home with his parents. Spooner is fairly set in his unfulfilling routine, but turning 30 marks a hard deadline set by his mom and dad to get a place of his own. To top it off, Spooner's boss is putting on the pressure to bring in some numbers, or face the chopping block. Headed for one of the worst days of his life, Spooner meets the girl of his dreams, Rose (Nora Zehetner). Forgoing all other priorities, Spooner is now working on winning her heart, but on their perfect date, she breaks the news that she is about to leave for the Philippines. How far will Spooner go to keep Rose in town and show her he really knows how to spoon?