Robert Noonan (known in Thomaston as Bobby Marconi) returns to Thomaston from military academy after his mother has fled to Jacksonville, Florida. Through nested flashbacks, the narrative reveals his mother’s history of failed escapes from her controlling, abusive husband. When Robert was six, his father caught her fleeing, smashed her suitcase, and threw her clothes into the street. Young Robert gathered them. Later attempts were similarly thwarted by his father’s surveillance network and financial control.

A pivotal escape occurred when Robert was in sixth grade. Using his paper route savings, he helped fund her bus trip to Montreal, but she was stopped at the border and had a medical crisis. At the academy, Robert experienced an epiphany: His father, despite his threats, had never actually struck anyone—he was a cowardly bully. He also realized his mother’s cruel nickname, D.C., stood for “Dumb Cunt.”

Back home, Robert picks up his mother from the train station after secretly cleaning the house in defiance of his father. His mother has negotiated a promise from his father to let her get her tubes tied after this baby. At home, she immediately goes into labor. After the baby is born, Robert threatens his father: If he ever impregnates his mother again or uses that nickname, Robert will kill him.

Lucy calls, inviting Robert to Ikey Lubin’s to meet his girlfriend, Sarah Berg, who drew a picture including Robert years ago. At the market, Sarah greets him warmly, showing him her drawing of the store with Robert depicted on the threshold. Driving Robert home, Tessa asks him about his mother, warning him that he won’t be able to protect her from his father for long, since he’ll be graduating and moving away soon. She also predicts he’ll become interested in Sarah. Over the summer, Robert becomes a fixture at Ikey’s. When Sarah returns from Long Island in September, he’s struck by her transformation and confused by his attraction to his friend’s girlfriend.

On the first day of senior year, Robert learns he’s been moved into Mr. Berg’s honors English class. He assumes Sarah arranged it as a romantic signal, then discovers that she’s in the class he was removed from—she moved him away from their only shared class.

Mr. Berg arrives gaunt and disheveled, accompanied by Three Mock, who has ongoing brain injury from being beaten by Perry Kozlowski years earlier. Berg’s iconoclastic teaching begins: He writes Langston Hughes’s poem “Hope” on the board and leads the class in a close reading, noting that Three, the only Black student, is the only one who knows what the “dream book” in the poem refers to. He admonishes the white students that, so long as they remain invested in a system of racial injustice designed to remain invisible to them, they will never understand this poem. He smokes in class, offering Robert a cigarette, and relentlessly questions students about their parents and their assumptions. When Perry Kozlowski protests the cigarettes, Berg creates a trap of complicity. He goads Perry about race and class, probes Nan Beverly about her rich father, and gets Robert to identify Lucy as caught between his believing father and doubting mother. Lucy has a “spell,” feels faint, and must see the nurse.

That evening at Ikey’s, Robert and Lucy remain giddy from the strange class. Tessa speculates that Berg is trying to get fired. That night, Robert’s drunk father appears in his doorway, saying Robert has the wrong answers because he has not asked the right questions—words eerily similar to Berg’s teaching. Robert realizes Lucy never mentioned his supposed best friend David Entleman, whose death by suicide Berg referenced in class. He has an unwelcome thought about stealing Sarah from Lou, then resolves to keep Berg at arm’s length despite the exhilarating classes.

In the present, Lucy arrives at the junior high art room to view his wife Sarah’s new painting. The custodian, Tom Shipley, unlocks the door for him. Lucy sees the painting and is immediately moved, recalling his feelings upon seeing Sarah’s first drawing as a child. It depicts Venice’s Bridge of Sighs, a stone passage connecting the Doge’s Palace to the prison, where convicts’ despairing sighs are said to have across the canal.

His thoughts drift to Gabriel Mock and the night Whitcombe Hall burned down, which coincided with Perry Kozlowski’s return to Thomaston to give the high school commencement address. Gabriel had disrupted Perry’s speech to remind everyone that Perry beat Three into a coma when they were children, leaving him with lifelong brain damage. Three had since died in Vietnam, leaving Gabriel feeling doubly vengeful. He was arrested for the fire, and Tessa insisted they post his bail.

Staring at the painting, Lucy finally succumbs to one of his “spells,” which he’s been flirting with all day. He feels himself enter the painting’s world, stepping onto the Bridge of Sighs. Sarah’s voice calls him back, but he’s ashamed of something he hid in his desk drawer and wants to stay. On the bridge, he encounters his dead father, Big Lou, who reminds him of a childhood promise never to drift away. Lucy protests that he’d rather stay with his father.

Sarah’s voice grows closer. Lucy opens his eyes to find her kneeling beside him, holding his hand, having brought him out of the “spell.”

Sarah Berg reflects on her divided life between her separated parents. Her father is an ascetic whose Thomaston household runs on rigid schedules. Her mother lives chaotically at the Sundry Arms, a Long Island apartment complex for divorced men run by Harold Sundry. Her mother has become voluble since the separation, expounding cynical philosophies about marriage and freely entertaining male visitors. Sarah sometimes overhears late-night conversations and finds martini glasses on the doorstep.

Her father remains unaware of her mother’s lifestyle, wrongly assuming she struggles financially. Sarah suspects her father has a secret drug dependency.

Sarah is a popular babysitter on Long Island. One summer, her favorite family offers her their garage apartment as a live-in arrangement with a studio. Though tempted, she lies to her mother, saying she declined, not wanting to hurt her feelings. That marriage soon collapses anyway.

By the summer before senior year, Sarah harbors a secret of her own: inexplicable, powerful feelings for Bobby Marconi, whom she has met only once. When she mentions him to her mother, she receives harsh warnings about the Marconi family genetics.

Sarah realizes drawing is her way to understand confusing emotions. She decides to compromise—she’ll draw Bobby again, but not until summer’s end, hoping the spell will break itself.