Audre is a 16-year-old junior class president and debate team captain at Cheshire Prep in Brooklyn. She plans to write a self-help book to boost her Stanford application. She struggles with anxiety and a crippling need for perfection. To push herself outside her comfort zone, she hires a transfer student to help her complete a list of daring experiences.

Bash is a 17-year-old transfer student from California who recently moved in with his estranged mother in Brooklyn. Though he has a wild reputation among the student body, he is actually calm and deeply passionate about tattoo artistry. He agrees to help Audre complete a series of daring challenges, bringing a relaxed approach to her highly regimented life.

Eva is a highly successful author and Audre's mother. She frequently experiences severe migraines but hides her pain from the public. While she deeply loves her family and wants the best for Audre, her exacting standards and secretive nature create tension in their household.

Reshma is Audre's 16-year-old best friend, born in India and adopted by British pop stars. She lives an opulent but lonely life, often acting out or meddling in others' affairs to stave off boredom. She writes the list of daring experiences that pushes Audre to hire a fun consultant.

Shane is an acclaimed author and Eva's fiancé, actively planning their upcoming wedding while managing his own recovery from alcohol addiction. He is a stable presence in the household, attempting to balance his career with caring for his new baby and supporting Audre.

Clio is a freshman at Cornell University who volunteers in Prospect Park. She is the only person in New York who knew Bash before he moved from California, and she persistently urges him to reach out to his estranged father.

Ellison is Audre's former prom date. He presents an image of an upstanding student worried about his college admissions, but he holds a damaging secret over Audre's head. His actions cause her severe anxiety and prompt her to avoid social situations.

Milton is the director of track and field at California University and a former Olympic hopeful. He is an intense, demanding figure who disowned Bash and forced his son to move across the country.

Sparrow is a classmate of Audre and Reshma at Cheshire Prep. She has a strong crush on Bash Henry and frequently worries about how to change her appearance to attract his attention.

Lizette is Eva's mother and Audre's grandmother. She is a former model and pageant queen who now runs her own business. Her demanding nature and complicated history cast a long shadow over the women in her family.

Jennifer is Bash's estranged mother who owns a gift shop called Just Because in Brooklyn. She spends much of her time traveling to volunteer with underprivileged youth, remaining largely absent from her own son's daily life.

Mack is the owner of Fifth Angel Ink Designs in Myrtle Beach. Impressed by Bash's art portfolio, he offers the young artist a chance to audition for a position at his studio.

Manny is a boy Audre knows through the school debate team. He becomes the target of Audre's attempt to complete one of her daring challenges by kissing a boy at a party.

Alice is Audre's one-year-old half-sister. Her arrival has caused massive changes in the family's apartment layout and dynamics, leaving Audre feeling pushed aside.