Jessie is a sixteen-year-old junior who recently relocated from Chicago to California after her father eloped. She secures an after-school job at a local bookstore called Book Out Below! while trying to survive the exclusive social hierarchy of Wood Valley High School. Still heavily grieving her mother's death from ovarian cancer, she feels numb and out of place in her new affluent environment.

Ethan is a quiet, observant junior at Wood Valley High School who frequently wears a Batman t-shirt. He pairs up with Jessie for an AP English project on T.S. Eliot's "The Waste Land." He frequently appears exhausted and withdrawn from his peers, preferring to read poetry when he cannot sleep.

Theo is Jessie's new stepbrother and a fellow junior at Wood Valley High School. He dresses theatrically and presents a confident, flamboyant exterior to his peers. Beneath his dramatic persona, he experiences severe anxiety and resentment over his mother's sudden marriage.

Scarlett is Jessie's tough, witty best friend who remained in Chicago when Jessie moved away. She regularly provides reassurance and advice through text messages and phone calls. Her physical distance forces her to handle her own high school transitions and romantic developments without Jessie's immediate physical presence.

Adrianna is a friendly junior who welcomes Jessie into her social circle alongside her friend Agnes. She harbors a strong crush on senior musician Liam Sandler. Her welcoming attitude provides Jessie with an early anchor in an otherwise hostile school environment.

Liam is a senior at Wood Valley High School and the newest guitarist for the student band Orgasmville. He gives up some of his working hours at the local bookstore so his mother can hire Jessie. He is dating Gem, one of the wealthy girls in Jessie's class.

Bill is Jessie's father, who recently relocated his daughter from Chicago to Los Angeles. After losing his first wife to cancer, he met Rachel in an online bereavement group and eloped shortly after. He struggles to manage his daughter's emotional needs while adjusting to his own new life in California.

Rachel is Jessie's wealthy new stepmother and Theo's biological mother. She met Bill online after the death of her first husband and quickly married him. She tries to manage the newly blended household but her energetic presence feels exhausting to Jessie, who resists her attempts at connection.

Agnes is a student at Wood Valley High School and a close friend of Adrianna. She quickly accepts Jessie into their friend group and offers candid opinions about their wealthy classmates.

Gem is a wealthy, blonde student at Wood Valley High School who immediately targets Jessie for bullying. She relies on her family's financial status to evade consequences for her malicious behavior.

Crystal is a blonde student at Wood Valley High School who follows Gem's lead. She actively participates in gossiping about Jessie during their classes.

Mrs. Pollack is the AP English teacher at Wood Valley High School. She notices the hostility Jessie faces from other students and attempts to intervene, though her initial approach only alienates Jessie further.

Mrs. Sandler is the owner of the local bookstore, Book Out Below!, and Liam's mother. She offers Jessie a job and provides a comforting, maternal presence when Jessie has difficult days at school.

Caleb is a senior at Wood Valley High School who is friends with Liam and Ethan. He occasionally helps the school band write their music and is frequently seen around the campus.

Adam is a high school student in Chicago. He dates Scarlett, introducing new romantic pressures and anxieties into her life while her best friend is living across the country.