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Oliver is a boy who knows what he has, but not what he wants. Samantha is a girl who knows what she wants, but not what she has. When the two of them break up, both are devastated. Oliver knows that he wants nothing more than to "win her back," but how can he do that when he was the one who caused the breakup in the first place? He'll try his best with a little help and advice, from storybook characters that only he can see. As Don Quixote, Maid Marian, and others try to get him back on his feet, Oliver must answer a question for himself: What does it mean to love someone?