Henri is a high school senior, star student, and dog walker attending FATE Academy on a scholarship. As a first-generation American to Haitian immigrant parents, he relies heavily on his charm and carefully constructed personas to fit into his highly competitive environment. He harbors a secret passion for sneaker design while feeling immense pressure to fulfill his father's dream of attending Columbia University.

Corinne is a fiercely intelligent, intense senior at FATE Academy who lives in Henri's apartment building. Academically focused with her sights set on Princeton University, she struggles socially and enlists Henri's help to become more well-rounded. She is honest, direct, and challenges Henri to abandon his masks and discover his true passions.

Jacques is Henri's father and a Haitian immigrant who works tirelessly as a building manager on the Upper West Side. He places immense pressure on Henri to gain admission to Columbia University, viewing it as the ultimate realization of the American Dream. He routinely sacrifices his own personal ambitions to secure stability and opportunities for his family.

Jacques's brother and Henri's uncle, currently working as a doorman in a luxury building. Lion is a perpetual hustler who is willing to bend moral codes to get ahead, putting him at odds with Jacques. Despite his questionable methods, he possesses sharp insight into human nature and the realities of privilege.

Henri's wealthy best friend and fellow sneaker enthusiast. Born in China and adopted by Jewish parents in New York, Ming is fiercely loyal and completely unbothered by material differences. He provides unwavering support to Henri, demonstrating that true friendship extends beyond socioeconomic status.

Corinne's mother and the first Black female Dean of English at Columbia University. She is a strict, ambitious, and highly successful academic who holds high expectations for her daughter and those around her.

A wealthy, well-connected legacy student at FATE Academy whose family has donated millions to Columbia University. He represents the privileges and institutional advantages that Henri must work incredibly hard to overcome.

A wealthy student at FATE Academy who lives in a Tribeca penthouse. She has a casual arrangement with Henri but eventually confronts him about his assumptions regarding their relationship and what she actually wants.

The guidance counselor at FATE Academy. He tries to manage Henri's expectations regarding his chances of getting into Columbia and encourages him to consider other universities that fit his profile better.

An award-winning playwright and young Black alumna of Columbia. She conducts Henri's college interview and quickly sees through his rehearsed, synthetic answers, challenging him to articulate his authentic desires.

The hypervigilant captain of the FATE Academy debate team. He pushes Henri and the rest of the team to practice rigorously, reminding Henri that he cannot rely on charm alone to win arguments.