Plot
Novelist Grady Tripp teaches creative writing at a Pennsylvania university. He is having an affair with the university chancellor, Sara Gaskell, whose husband, Walter, is the chairman of the English department in which Grady is a professor. Grady's third wife, Emily, has just left him, and he has failed to repeat the success of his first novel, published seven years earlier. He continues to labor on a second novel, but the more he tries to finish it, the less able he finds himself to invent a satisfactory ending. He spends his free time smoking cannabis.
Grady's students include James Leer and Hannah Green. Hannah, who rents a room in Grady's house, is attracted to Grady, who does not reciprocate.
During a party at the Gaskells' house, Sara reveals to Grady that she is pregnant with his child. Grady finds James standing outside holding what he claims to be a replica gun. However, the gun is real, as James shoots the Gaskells' dog when he finds it attacking Grady. James also steals a valuable piece of Marilyn Monroe memorabilia from the house. Grady cannot tell Sara of this incident since she is pressuring him to choose between her and Emily. Grady keeps the dead dog in the trunk of his car for most of the weekend. He also allows James to follow him around, fearing that he may be depressed or suicidal. Gradually, he realizes that much of what James says about himself and his life is untrue, seemingly designed to elicit Grady's sympathy.
Meanwhile, Grady's editor, Terry Crabtree, has flown into town on the pretense of attending the university's annual WordFest, a literary event for aspiring authors. Terry is actually there to see if Grady has written anything worth publishing, as both men's careers depend on the unfinished book. Terry arrives with a date whom he met on the flight, a trans woman named Antonia Sloviak. The pair have sex in a bedroom at the Gaskells' party, but immediately afterward, Terry meets James and becomes infatuated with him, and Antonia is unceremoniously sent home. After a night on the town, Terry and James semi-consciously flirt throughout the night, which leads up to the two having sex in one of Grady's spare rooms.
Tired and confused, Grady phones Walter and confesses that he is in love with Sara. Meanwhile, Walter has made the connection between the disappearance of the Marilyn Monroe memorabilia and James. The following morning, the police arrive with Sara to escort James to her office to discuss the ramifications of his actions. The memorabilia is still in Grady's car, which has conspicuously gone missing. The car had been given to him by a friend as payment for a loan, and, over the weekend, Grady has come to suspect that the car was stolen. Throughout his travel around town, a man claiming to be the car's real owner repeatedly accosted Grady. He tracks the car down, but in a dispute over its ownership, the majority of his manuscript blows out of the car and is lost. The car's owner gives him a ride to the university with his wife Oola in the passenger seat, along with the stolen memorabilia.
Grady finally sees that making things right involves having to make difficult choices. He tells the story behind the memorabilia and allows Oola to leave with it. Worried that Grady's choice comes at the expense of damaging James's future, Terry convinces Walter not to press charges by agreeing to publish his book about Joe DiMaggio and Marilyn Monroe.
Hannah graduates and becomes a junior editor. James drops out and moves to New York to rework his novel for publication. Terry "goes right on being Crabtree." Grady finishes typing his new book – now saved on a computer – which is an account of the recent events, then watches as Sara and their child arrive home.
