Emilie is a high school junior in Omaha, Nebraska, who relies on strict schedules and pros-and-cons lists to manage her life. Deeply affected by her parents' messy divorce, she uses meticulous planning to avoid repeating their mistakes, especially regarding romance. She strives for academic perfection to secure a college scholarship.

Nick is Emilie's enigmatic chemistry lab partner. He drives a truck, listens to Metallica, and openly expresses his distaste for Valentine's Day. He maintains a cynical view on love and happiness, believing that contentment is fleeting and easily lost.

Josh is a highly motivated and academically successful student involved in debate and mock trial. Emilie views him as the perfect boyfriend on paper, admiring his ten-year plan and confident demeanor. He dresses neatly, often in leather accessories, and maintains a charming presence at Hazelwood High.

Macy is Josh's ex-girlfriend. She remains actively present at school, creating an awkward dynamic that interferes with Emilie's carefully planned anniversary and causing Emilie to question her seemingly perfect relationship.

Max is Emilie's grandmother, providing a safe haven when Emilie's home life becomes overwhelming. She is outspoken and encourages Emilie to stop trying to please everyone else and openly express her true emotions.

Emilie's father shares custody of her following his divorce. He works a job that recently offered him a promotion in Houston, Texas, prompting him to plan a move across the country with his new wife and children, a decision that deeply hurts Emilie.

Emilie's mother shares custody of Emilie in Omaha. She and her ex-husband have a strained history that impacts Emilie's sense of stability, often leaving Emilie feeling out of place between two separate households.

Lisa is Emilie's stepmother, married to Emilie's father. She manages a busy household that includes her twin boys and often expects Emilie to accommodate her younger children's schedules.

Joel is Emilie's younger brother who lives at her father's house. His morning routine frequently disrupts Emilie's carefully timed schedule when they have to share a bathroom.

Chris is one of Emilie's close friends at school. He frequently points out Emilie's obsession with checklists and control, offering honest feedback about her relationship with Josh.

Roxane, often called Rox, is another of Emilie's good friends. She supports Emilie through her stressful school days and provides a sounding board for Emilie's relationship troubles.

Mrs. Bowen is an administrator handling the prestigious summer journalism program at Hazelwood High. She holds the responsibility of informing students about their fellowship application statuses.

Todd is Emilie's stepdad, married to her mother. He lives with them in Omaha and forms part of the divided family structure Emilie experiences.

Eric is Nick's deceased brother, who died in an ATV accident. His death heavily impacts Nick's outlook on life and creates a lingering grief that Nick struggles to process.

Dante is a tattoo artist who works with Nick. He notices Nick's changing demeanor and cares about his coworker's well-being following a personal tragedy.