In the summer of 1942 on the fictional New England Packett Island (based on the real-life Nantucket Island), 15-year-old "Hermie" and his friends – jock Oscy and introverted nerd Benjie – are hanging out on the beach. They spot a young soldier carrying his new bride into a house and are struck by her beauty.
They continue spending afternoons on the beach, where their thoughts turn to sex. All of them are virgins: Oscy is obsessed with the act of sex, while Hermie develops romantic interest in the bride, whose husband he spots leaving the island on a water taxi one morning. Later that day, Hermie sees her outside the market struggling with grocery bags. He offers to carry the bags home, which she gladly accepts, and in this way, gets to meet her.
Meanwhile, Oscy and Hermie become convinced they know everything necessary to lose their virginity. They test this by going to the movies and picking up a trio of high-school girls. Oscy stakes out Miriam, "giving" Hermie her less attractive friend, Aggie, and leaving Benjie with Gloria, a heavyset girl with braces. Frightened by the potential of sex, Benjie runs off. The other two girls initially refuse to go without Benjie's would-be date, but she says to go without her, then leaves herself. The war bride, who is also at the theater, sees Hermie and asks if he can help her move some boxes on Thursday. During the film, Oscy attempts to fondle Miriam and eventually makes out with her. Hermie succeeds in kissing Aggie, who allows him to grope what he thinks is her breast; Oscy later points out that Hermie was fondling her arm.
On Thursday, Hermie helps the bride move boxes into her attic, and she thanks him with a kiss on the forehead. Later, in preparation for a marshmallow roast on the beach with Aggie and Miriam, Hermie goes to the drugstore and amusingly builds up the nerve to ask the druggist for condoms (or "rubbers", as they were known in the '40s). That night, Hermie roasts marshmallows with Aggie while Oscy has sex with Miriam behind the dune bushes. Oscy returns and asks Hermie for some condoms. Aggie, wondering what is going on, walks over to Oscy and Miriam, sees them having sex, and runs home, upset.
The next day, Hermie comes across the bride sitting outside her house, writing a letter to her husband. Hermie offers to keep her company that night, and she accepts. Hermie says he does not know her name and she replies her name is Dorothy. Later, Hermie runs into Oscy, who relates that Miriam's appendix burst and she has been rushed to the mainland. When Oscy asks about Dorothy and makes crude comments, Hermie rebukes him for his crassness.
When Hermie arrives at Dorothy's house that evening, he finds it strangely quiet. He sees a spinning record with the needle stuck in the run-out groove, a bottle of whiskey on a table, a burning cigarette in an ashtray and next to it a telegram. Dorothy's husband has been killed in action, his plane shot down over France. Dorothy comes out of her bedroom in tears. She greets Hermie, switches on the phonograph then walks into the kitchen and begins washing dishes. Hermie says, "I'm sorry." Dorothy turns toward Hermie, slowly approaches him and silently lays her head on his shoulder and they dance together, both in tears; then they kiss. Taking his hand, she leads him to the bedroom. They silently undress and Dorothy draws Hermie into bed and gently makes love with him. Afterward, she withdraws to the porch. Hermie approaches her, and she tells him goodnight. He then leaves, his last image of Dorothy being of her leaning against the railing as she smokes a cigarette and stares into the night.
The next day, Hermie and Oscy reconcile, with Oscy informing Hermie that Miriam will recover. Oscy is curious about what happened with Dorothy, but Hermie remains silent. Hermie returns to Dorothy's, only to find the house deserted. She has left behind a letter for Hermie explaining that she must return home and that in time he will find a proper way to remember what happened between them. She assures him that she will remember him and hopes he will be spared from life's senseless tragedies, wishing him "good things, only good things", signing, "Always, Dorothy."
In the finishing narrator voiceover, the adult Hermie notes that he would never see Dorothy again nor learn what became of her. The film concludes: "In the summer of '42 we raided the Coast Guard station four times, we saw five movies and had nine days of rain. Benjie broke his watch, Oscy gave up the harmonica, and, in a very special way, I lost Hermie. Forever."
Hermie visits Dorothy after learning her husband has been killed in action; their night together marks the end of his innocence and the beginning of adulthood. Dorothy leaves Hermie a heartfelt note before departing, and Hermie is left to contemplate the impact of their brief, poignant connection.
The ending signifies Hermie's passage from youth to maturity through a bittersweet, life-altering experience. Dorothy's grief and Hermie's empathy intertwine in a moment that is less about physical intimacy and more about emotional awakening. The film closes with Hermie reflecting on the summer that changed him, echoing the universal pains and memories of growing up. It's a meditation on longing, loss, and the indelible marks left by fleeting encounters.