Rachel Stevens is a 29-year-old high school English teacher from California who takes on the responsibility of chaperoning three of her students—a meticulous Margot, the easygoing Sam, and the gifted yet troubled Billy—to a weekend drama competition. On their first day, after a meeting with the principal concerning logistical details, Rachel learns that Billy is dealing with a behavioral disorder and is on medication. Upon their arrival at the hotel, Rachel encounters another teacher, Walter, and despite the apparent tensions of his marital status, they indulge in an awkward sexual encounter.
Later that night, upon returning to her room, she finds Billy looking distraught outside his door. He brushes off her concern with a light-hearted excuse about losing his key, leaving Rachel to spend the evening in solitude, drinking and rehearsing her classroom dialogues.
The following morning presents new challenges as Rachel takes Billy to the mechanic to fix a flat tire, while the other students engage in their rehearsals. During their mile-long walk to a nearby diner, a conversation about her sexuality arises, leading Rachel to assert that they’re veering into inappropriate territory. Back at the hotel, Sam informs Billy of the missed critical rehearsals.
As they compete, Margot falters during her recitation of A Streetcar Named Desire, provoking Rachel’s support. Margot reveals that the trip's funding came from her parents, along with her belief that if Billy shines in the competition, it could mean more financial support for their school's arts programs. Tensions rise when Billy inadvertently calls Rachel by her first name during dinner, alarming her and the other students.
Rachel seeks comfort from Walter, who ultimately turns her away, pushing her to return to her room dejectedly. Billy then arrives to apologize for the dinner faux pas; witnessing her sadness, he forces his way into her room, attempting to lighten the mood by bouncing on her bed. This leads to an unexpected moment of intimacy where Rachel reveals her lingering grief over her mother's death the previous year. Their connection deepens as Billy comforts her, though it quickly becomes apparent that this closeness is inappropriate.
The situation escalates when Sam and Margot interrupt, leading to further complications as they share their own romantic woes. Billy, feeling pushed out, reacts with frustration and storms out, leaving an unsettling silence.
The next morning, Billy delivers a passionate rendition of his monologue from Death of a Salesman, earning Rachel's applause and a private confession from him that he's not taking his medication. Realizing the precarious situation, she attempts to reach the principal but to no avail, leading to an encounter with Walter, who encourages her to detach from her students more.
At the awards ceremony, Billy wins second place, and as they journey back, their earlier tension is palpable. A reminder from Margot about a makeup test for The Great Gatsby leads the students to create a clever scheme to help Billy pass, culminating successfully.
Upon returning to school, Rachel recommends that Billy talk to his parents about his medication. In a poignant moment, he suggests that she, too, needs someone to take care of her. After a brief pause, she exits her car, ready to approach Billy and his family with a warm smile, signifying a new chapter for both she and her students.
