Struggling writer Vincent meets his beautiful girlfriend Angela at the train station. They're a happy couple until he proposes. She leaves him suddenly in the middle of the night. Vincent runs to the train station after Angela but is too late.
Vincent tries to start over by moving from Sleepy Hollow to New York for a new teaching job. His surly attitude makes his students unhappy and lands him in the office of psychologist Katherine. Angela resurfaces in an old bookstore and Vincent sees her disappear behind a door. The doorkeeper bars Vincent from following and mysteriously says the door leads to the past.
Vincent gives his unfinished novel about Angela to Katherine and his ex-student Drew to read. Vincent and Katherine become romantically involved, but she's unhappy that he hangs on to the Sleepy Hollow house where he lived with Angela. Meanwhile, Drew advises Vincent to rewrite the novel's ending and accuses Vincent of making it up. (Well, it is a novel.) Vincent admits he made up the part where Angela left on a train.
Vincent returns to Sleepy Hollow to sell his house. He recalls the night he proposed to Angela. She was upset because her mother had committed suicide after her father left for another woman. Angela returns and Vincent resumes his relationship. Vincent wakes up and finds Katherine present and Angela missing. Katherine claims she and he have been together all that time. Vincent evicts Katherine and wanders around the city streets of New York at night. Simultaneously he enters the bookstore door-to-the-past and Katherine's apartment door. Inside, he finds Angela underwater in a bathtub. Vincent confesses that Angela never existed. It was his mother who died when he was young after leaving him a toy train set. Vincent and Katherine reunite at the train station.