Before her therapy session, Phoebe decides to sit at the beach near the Santa Monica Pier where she and Jonathan used to come together after they graduated from college. She reminisces about a time when she and Jonathan had noticed a teacher supervising a group of children on a field trip. Phoebe had discovered that they were from one of the schools to which she had applied, and Jonathan had encouraged her to put herself out there and approach the teacher, who turned out to be Cheryl. Phoebe’s ability to de-escalate a conflict between two students impressed Cheryl, which directly led to her getting her teaching job at Brentwood Friends Academy.

In the present, Phoebe hopes for a sign that her friendship with Jonathan will recover. Suddenly, Finn appears carrying a surfboard and stops to talk to her. Phoebe learns that he’s 24, five years younger than her. At her therapy session, Phoebe spends most of the time discussing Finn and her plan to get a ride home from him after the school’s upcoming Fall Ball, hoping the charged moment of a nighttime drop-off will lead somewhere. Her therapist, Sandy, questions whether Phoebe’s intense focus on Finn is a way to avoid her more significant issues with Jonathan and Matthew. Phoebe dismisses this, leaving the session confident that her relationship with Finn will soon progress.

Jonathan arrives home late, and the interaction with Phoebe is immediately strained and distant. He eats cold pizza at the kitchen table instead of joining her on the couch as he normally would. They attempt their shared ritual of the Monday crossword puzzle but fail to complete it. As they head upstairs, Phoebe asks him if he thinks they will regain their former closeness. Jonathan reassures her that they will, but he avoids eye contact, prompting Phoebe to realize she can no longer understand his feelings. He promises things will be fine and takes her hand.

Phoebe attends the Brentwood Friends Academy Fall Ball with a plan to get Finn to drive her home. At the dance, the principal, Dan, first announces a two-glass punch limit, referencing last year’s punch-induced breakdown by teacher Jane, then announces that the school has “decided to outlaw grinding altogether this year” (192), which makes Finn and Phoebe laugh. Encouraged, Phoebe makes sure Finn overhears that her car is in the shop.

Later, when the principal asks her to schedule an interview for the assistant principal position, Phoebe agrees though she remains undecided about taking the job. She and Finn share a pleasant conversation over punch, and he confirms she is invited to Noah’s upcoming party. As the dance ends, Teacher Rob enthusiastically offers Phoebe a ride home before she has a chance to ask Finn. As Finn leaves, he gives her a curtsy, and she dejectedly prepares to go home with Teacher Rob.

Phoebe gets a ride with Teacher Rob and the dance’s emcee, DJ Spider, whose real name is Nick. In the messy car, Nick lights a joint and passes it around. Phoebe smokes and has an immediate, intensely negative reaction. Believing she’s experiencing a medical emergency, she tries to calm herself by breathing deeply and repeating comforting mantras in her head. Her paranoia escalates as she uses her phone to google her symptoms, convincing herself she is suffering from a series of fatal conditions, including pulmonary edema and an aneurysm.

When they pull up to the bus stop to drop off Nick, he exits the car and Teacher Rob invites Phoebe to sit up front. Instead, she gets out as well, tells him the drop-off is perfect, and walks away. She goes to a nearby Carl’s Jr., orders food, and calls Jonathan for help. Jonathan picks her up, and she realizes she has already misplaced the milkshake she bought for him. His presence immediately soothes her panic, and she feels safe as he drives her home.

Feeling confident, Phoebe dresses up to impress Finn at Noah’s birthday party. She invites Jonathan to join them, but he quickly declines. On the way, Meg reveals she and Noah have been on several dates, making Phoebe feel like an inattentive friend. At the party, Phoebe’s confidence dissolves as she feels overdressed and out of place among Finn’s friends. She wanders off to find the bathroom and enters Finn’s bedroom, where she is struck by the familiar scent of Jonathan’s cologne. Under the bed, she discovers one of Jonathan’s favorite green T-shirts. In a moment of horrifying realization, Phoebe checks her Find My Friends app and confirms that the location she believed was his new girlfriend Sydney’s house has been Finn’s apartment all along. Overcome with nausea and shock at the truth of Jonathan and Finn’s secret relationship, she abruptly leaves the party and runs home. Jonathan opens the door, and Phoebe confronts him by silently handing him his shirt. Devastated, she goes to her room and collapses into bed.

Overwhelmed by the events of the previous night, Phoebe takes a sick day from work for the first time. She finally understands what Jonathan has been trying to communicate and feels consumed by guilt that she failed to understand what he was going through. Her despair deepens when she learns from a group chat that her friend Nora is moving to San Francisco for a new job in less than two weeks. Phoebe realizes she never even knew Nora had applied for the job. Believing she has hit rock bottom, Phoebe finds a new sense of urgency to make changes. She systematically gathers all her beloved romance novels, which she now views as propaganda, along with her laminated list, puts them in trash bags, and leaves them on the sidewalk for anyone to take. On her fridge, Phoebe notices a graduation photo of her and Jonathan, and feels overcome by the importance of their friendship in her life. She immediately grabs her keys, walks out the door, and begins to drive.