In 1951, Marcus, a working-class Jewish student from New Jersey, attends a small Ohio college, where he struggles with sexual repression and cultural disaffection, amid the ongoing Korean War.
Set in 1951, the story follows Marcus Messner, the idealistic son of a humble kosher butcher from Newark, N.J. Marcus leaves for Ohio to study at a small, conservative college, where he finds himself at odds with the administration, grapples with anti-Semitism and sexual repression and pines after a troubled girl.—THR
Marcus Messner (Logan Lerman) is fighting in the Korean War. After a serious bayonet injury during an encounter with Chinese troops, he reflects on the choices he made in his life and how they led him to where he is now.
In a flashback to the summer of 1951, before his first year of college, Marcus's synagogue in Newark, New Jersey mourns the death in Korea of one of his classmates. Marcus has been awarded a scholarship to Winesburg College, a private Christian school in Ohio, which allows him to defer the draft. His father (Danny Burstein), who runs a kosher butcher shop, is unnerved by the deaths in the war of boys like his son and becomes overwhelmed with paranoia.
At Winesburg, Marcus is a studious, introverted pupil who feels disconnected from the rest of the student body, including fellow Jewish students. He meets Olivia Hutton (Sarah Gadon), a beautiful student majoring in French literature. The daughter of a Cleveland surgeon, Olivia is freethinking, sophisticated, and sexually frank, but also fragile and disturbed; she feels as alienated and out-of-place as Marcus. On their first date, Olivia ends the evening by performing fellatio on him. The inexperienced sexual virgin Marcus is so shocked that he avoids her for several weeks. As he and Olivia continue to have sexual relations without intercourse, he learns that she is a recovering alcoholic who had been previously enrolled at Mount Holyoke College. After she attempted suicide, she was admitted to the Menninger clinic. Olivia's parents sent her to Winesburg hoping that the "squareness" of the school would help her become stable. She also makes allusions to having been sexually abused by her father.
Marcus decides that he can no longer tolerate his noisy, intrusive roommates and requests to switch to a single room. The university administration schedules a meeting with Dean of Men Caudwell (Tracy Letts). Though the discussion is ostensibly about the change in his living situation, it becomes an interrogation about Marcus's atheist beliefs and his dislike of Winesburg's conservative culture. The already ill Marcus becomes so agitated that he vomits and passes out.
Marcus is rushed to the hospital, where he has an operation for appendicitis. During recovery, he is visited by a senior student who informs him that Olivia has given blow jobs to nearly everyone else on campus. Marcus's mother Esther (Linda Emond) also visits him and says that she wants a divorce from his father, who is growing increasingly deranged and can no longer run the shop. In Marcus' hospital room, she meets Olivia, who has come to bring a red and white rose bouquet. During their visit, she observes her wrist scar from the suicide attempt. Later, while Marcus observes from his hospital window, they speak before departing from the hospital grounds; he sense his mother's disapproval of Olivia. The next day, Marcus' mother apologizes to him for oversharing her marital problems and promises not to divorce, but only if he ends his relationship with Olivia. She warns him of the dangers of getting too involved with people with mental illnesses, that her neediness would ruin his potential.
When Marcus returns to school, he finds that Olivia has disappeared from the campus and goes to Dean Caudwell to find out what happened to her. Olivia suffered a nervous breakdown and was hospitalized again. The school had been hesitant to accept her, given her history of electroshock therapy and relapses, but her father was an esteemed Winesburg alumnus who requested her admission. The Dean demands to know whether Marcus raped and impregnated Olivia; Marcus is outraged and leaves after using an obscenity. Marcus is then expelled after the Dean learns that he paid a student proxy (to evade the mandatory chapel requirement, and is drafted.
In Korea, Marcus is stabbed with a bayonet during combat. As he collapses, he thinks back to Olivia and wishes that he could tell her that "it's okay, whatever it is. 'Cause someone did love you. At least, I think that's what it was." Decades later, a gray-haired Olivia is seen living in a nursing home. She looks at the repeating red-and-white rose pattern on the wallpaper, and smiles.