Daisy is a homemaker and former fourth-grade teacher living in a 1970s middle-class American suburb. She practices intensive parenting, cooking family meals and overseeing her son's homework when he begins to struggle. Insecure about her family's social standing, she worries that school authorities view her and her husband as failures. She frequently second-guesses her parenting decisions, caught between her own difficult adolescence and the strict expectations of her current environment.

Donny is a fifteen-year-old high school student experiencing a difficult transition into adolescence. He is moody, frequently uncommunicative, and outwardly dismissive of his parents' values. His academic performance is poor, and he exhibits early signs of rebellion against the structured environment of his private school. He responds enthusiastically to adults who offer him leeway and validate his frustration with rules.

Calvin, who insists his clients call him "Cal," is a tutor specializing in youth who struggle with traditional schooling. He embodies the anti-authoritarian ethos of the 1960s, sporting longish hair, a handlebar mustache, and blue jeans. He operates out of a casual home office where teens congregate to listen to rock music and hang out under a basketball net. His tutoring philosophy prioritizes the whole child and personal autonomy over rigid academic discipline.

Matt is Daisy's husband and the primary breadwinner for the Coble family. He follows a traditional 1970s patriarchal model, spending most of his time at work and leaving the daily childrearing responsibilities to his wife. He wears threadbare suits, suggesting the family's middle-class status is financially precarious. He generally only involves himself in parenting during crises to enforce discipline.

Mr. Lanham is the principal of the private school Donny attends. He represents traditional institutional authority and standard middle-class academic expectations. He initiates the series of outside interventions into the Coble family's life by suggesting Daisy oversee Donny's homework and delivering news of Donny's truancy.

Amanda is Donny's younger sister. She occupies the periphery of the Coble household, quietly observing the family dynamics. As her parents invest increasing amounts of time, energy, and financial resources into managing her older brother's behavioral issues, she receives far less attention.

Miriam is Donny's teenage girlfriend. She adopts a rough, biker-inspired aesthetic, frequently wearing a motorcycle jacket. She is surly and uncommunicative around adults, actively avoiding visits with Donny's parents. Her presence signifies Donny's developing independent social life away from his family's expectations.