The anatomy of his life is starting to weigh on David, a recent college graduate, as he recognizes where his decisions have led him. At his lowest he meets a mysterious girl, Kelly, who sees his talent and tries to propel his guarded aspirations. Through a casual discussion of the tale of Rip Van Winkle, David discovers a parallel between his own life and the man that slept his life away. Fearing that his life will pass him by, David must make a choice. Will he choose the path of happiness and a life of fulfillment? Or will he follow Rip's path, and one day wake up in a world that forgot him?