Slacker bumpkin Reilly Brandt spends the majority of his young life's time romancing girls on monkey bars, writing short stories about penguins, and throwing watermelons at people. Meanwhile his artistically inclined and college bound friend Oliver Price debates with him endlessly on moving away from the town in which they both grew up and are from, Stosselville. Somewhere along the way Reilly meets a sweet and sexy coffee vixen named Charlotte Graham, who challenges Reilly on his notions of love, life and leaving.