During Christmas 1942, in the small northern California coastal town of Port Muir, seventeen-year-old Henry “Hopper” Nash and his best friend Nicky have six weeks remaining until they join the Marines. In the meantime, the two boys work at the bowling alley, where they reset pins and often mock the rich kids in town, whom they call “Gatsbys.” While Nicky is impulsive and determined to have as much as fun as possible before they leave, Henry is more modest and has to be persuaded to join his friend on a double date. Alone at the movies one night, Henry is captivated by the beautiful girl working in the ticket booth and anonymously sends her daisies. He secretly follows her home and assumes her family is wealthy as she enters a nice estate. At the library, Henry encounters her again and admits to leaving the daisies, but embarrasses himself by accidentally knocking over a bookcase. Later, the girl introduces herself as Caddie Winger and invites Henry to be her friend Gretchen’s date at a roller-skating event on Christmas Eve. Although disappointed he is not Caddie’s date, Henry agrees to go and pretends he has no plans to be with his family that night. After Caddie arrives at the event with a blind date, Michael, who is Gretchen’s cousin, she notices that Henry is very uncomfortable on skates. When he tumbles out of the rink, she recommends taking a break. While Gretchen and Michael continue to skate, Henry welcomes the chance to talk with Caddie alone. During their tentative conversation, Caddie finds Henry charming and suggests they get together later. Henry ignores Nicky’s warning about getting involved with a “Gatsby” girl, and takes her to one of his favorite places, an abandoned taproom on a seaside cliff. He impresses her with his piano playing, confessing that his mother forced him to learn when he would have preferred being on the baseball field. Following the outing, Caddie returns to the Donnelly estate, where she lives with her mother, Mrs. Winger, who works as the family’s maid. As a Christmas gift, Caddie receives a sweater from Alice, the Donnellys’ daughter, who is about the same age. Skipping school, Henry takes Caddie to a secluded pond, and the two make love after going skinny-dipping. He later tells Nicky that he thinks Caddie is “the one.” That night, the two boys get drunk and race to jump on a freight train, as they did when they were kids. After the stunt, Nicky confesses that his girl friend, Sally Kaiser, is pregnant and needs Henry’s help finding $150 for an abortion. Henry says he will think about it. He stays up until morning and goes to the cemetery, where his father, Mr. Nash, works as a gravedigger, to watch the funeral of a young serviceman. When Henry breaks free from school during a civil defense drill and meets Caddie dressed as a wounded soldier, she does not find the joke amusing. Caddie takes Henry along as she delivers library books to real injured soldiers at the veterans hospital. Henry is uncomfortable as one of the patients, a young amputee named Frank, talks to him. Afterward, Henry is annoyed at Caddie for trying to teach him a “lesson,” but also admits their relationship has made him think more about coming back from the war. When Caddie fancies a pair of dress shoes at a shop and resists the urge to buy them, Henry teases her about being a “Gatsby” girl. She does not say anything, but realizes he is under the impression that she is from a rich family. She arrives at the bowling alley one night hoping to resolve the misunderstanding, but Henry is too busy to talk. Nicky’s girl friend Sally also unexpectedly shows up and Caddie is curious why the girl is so upset. Meanwhile, Henry decides to help his friend obtain the abortion money and suggests they hustle two sailors at pool. However, the match turns into a close competition, and when Henry loses the final points, he and Nicky flee quickly to avoid paying the wager. Henry arrives at his house late for his own birthday party as his angry father and a confused Caddie greet him on the front porch. Desperate for the money, Nicky blurts out in front of Caddie that he needs $150. Henry reluctantly explains the situation, and Caddie says she will try and help. At the Donnelly residence, Alice catches Caddie stealing pearls, but is sympathetic and agrees to give her the money. Nicky, Henry, and Caddie later take Sally to a squalid trailer park, and the boys wait outside while Caddie stays with her during the abortion procedure and comforts the hysterical girl on the drive back home. The situation upsets Caddie, and when Henry tries to reassure her, she reveals her family is not wealthy. Crying, Caddie says she was afraid the truth would disappoint him and asks Henry to leave her alone. After watching her run away, Henry screams at Nicky for behaving so casually about the abortion risk and says he is tired of his troublemaking. Over the next week, Henry ignores Nicky’s attempts to reconcile. Noticing that the two friends are estranged, Mr. Nash tells his son that when Nicky was a young boy, he used to exhaust himself by sitting for hours at the grave of his recently deceased mother. As the start of their military service approaches, Henry makes peace with Nicky, stating that they have to “stick together.” Meanwhile, Henry leaves Caddie a treasure map. She follows the instructions and finds the dress shoes she wanted, by a tree. Henry is also there, and the two declare their love. At the train station, Mr. and Mrs. Nash say goodbye to their son and Nicky. Caddie gives Henry a photograph of her and embraces him. As the train begins to leave without them, Mr. Nash panics, while Henry and Nicky confidently race to catch it and jump onboard.