Jake is a thirteen-year-old with a reputation as a dangerous delinquent. Following his expulsion from several public schools in Rhode Island, his grandfather places him at The Creative Academy to avoid juvenile detention. He wears dark clothing and an eyebrow ring, and he styles his hair into scarlet spikes. He maintains a tough, standoffish exterior to intimidate others.

Edith, who prefers the name E.D., is the twelve-year-old daughter of the Applewhite family. Unlike her artistically inclined relatives, she values order and a structured curriculum. She takes her education seriously and feels entirely out of place in her eccentric, chaotic household. She deeply resents being paired with Jake for her coursework.

Randolph is the passionate and often hot-headed father of the Applewhite children. As a theater director, he frequently prioritizes his creative projects over practical household duties like grocery shopping. He advocates strongly for individuality and founded The Creative Academy to protect his children from the restrictive rules of traditional schooling.

Sybil is E.D.'s mother and a successful author of detective novels. She insists on using her maiden name to maintain her professional identity. Currently working on a complex literary project, she blocks out household noise with a white noise machine and often feels frustrated by her husband's lack of support.

Lucille is Archie's wife and a poet with a highly optimistic outlook. She practices meditation and shapes her vegetable garden based on the guidance of nature spirits. She is the one who originally proposed taking Jake into the family program.

Cordelia is E.D.'s older sister, a tall teenager who excels at multiple artistic pursuits. Currently focused on dance and choreography, she spends hours in the studio working on a solo project. She captures Jake's attention immediately upon his arrival.

Hal is E.D.'s fifteen-year-old brother and a reclusive sculptor. He rarely leaves his room, preferring to communicate through his closed door or window while loudly hammering away at his latest artwork.

Destiny is the highly energetic four-year-old youngest child of the Applewhite family. He possesses boundless curiosity and quickly attaches himself to Jake. E.D. takes it upon herself to tutor him, worried that his free-form education will leave him lacking practical skills.

Archie is Randolph's brother and Lucille's husband. He works alongside his father in the family woodshop, creating highly inventive and somewhat impractical furniture. He maintains a relaxed demeanor in contrast to his brother's intensity.

Zedediah is the patriarch of the Applewhite clan. He runs the family woodshop, crafting traditional, functional chairs. Unlike the rest of the easily distracted family, he pays close attention to the emotional needs of his grandchildren and offers E.D. grounding support.

Jeremy is a young journalist assigned to interview Sybil Jameson for a literary magazine. He quickly becomes fascinated by the entire Applewhite family's creative environment and decides he wants to write a book documenting their artistic dynasty.

Ravi Govindaswami is Lucille's spiritual guru. He is a serene, calm presence in the chaotic household. He takes charge of cooking for the family, preparing elaborately spiced meals while emphasizing the need for passion in all daily activities.

Henry is Jake's grandfather who lives in North Carolina. Frustrated by his grandson's disruptive behavior and unable to handle him, he arranges for Jake to live at Wit's End as a last alternative to juvenile detention.

Winston is the faithful family dog at Wit's End. He rapidly develops a close attachment to Jake. The dog follows him everywhere and provides the guarded teenager with unconditional companionship.