Seventeen year-old Jones (Elijah Wood) has decided to avoid college in favor of renting a room in a boarding house, and attempting to learn from life while trying to become a writer. As he tries to gain his mother's (Elizabeth Perkins) approval and figure out his father's whereabouts, he becomes involved with both Lisa (Mandy Moore), a struggling actress, and Jane (Franka Potente), an older photographer. When Jane gets into a car accident, and an ex-boyfriend comes to take care of her, Jones realizes how strong his feelings are for her. He then enlists his strange neighbor, Brad (Aaron Pearl), to help win Jane's love.