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The novel opens with a flash-forward: Kyle Chase, a fifteen-year-old sophomore, stands before a scene of shattered glass and blood while an unnamed figure nearby screams. Kyle tries to trace the chain of events that led here, concluding that everything went wrong before tenth grade even began. The narrative rewinds to the first day of school.

Kyle finds his name on the homeroom list at Midlands High School. His social circle, the "hoodies," named for the black sweatshirt jackets they all wear, is a group he fell into by default after his grades proved too low for Odyssey High, where his longtime friends enrolled. Max, the closest thing Kyle has to a best friend, teases him about Ashley Bianchi being in his homeroom. When Kyle's name is called, Ashley turns and smiles; he waves back, immediately feeling foolish. Kyle's disillusionment with school runs deep, cemented when he earned an A-plus on a book report he knew was fabricated.

Time passes uneventfully. The unifying principle of Kyle's life is simple: Don't get caught, whether copying homework, sneaking glances at Ashley, or stealing beers. On the Saturday before Halloween, Kyle and the hoodies discover an unlatched maintenance door at their old middle school. They slip inside, find nothing, and leave within minutes. In bed that night, Kyle registers that what they did constitutes breaking and entering, but the guilt passes quickly. Another line crossed.

Weeks later, Kyle finds a wallet in a stairwell. Before he can return it, its owner, Jake Burke, a large varsity lacrosse player, slams Kyle against the wall and accuses him of theft. Teachers intervene and both are sent to the principal's office. Jake's lacrosse coach asks Kyle directly if he took the wallet; Kyle explains he found it, and the coach believes him. The principal, however, cannot prove innocence or guilt. Kyle receives a three-day suspension for "starting a fight"; Jake gets one night's detention.

Interspersed through the narrative are three conflicting versions of how Kyle got a scar on his right hand: an official report stating he slipped and put his hand through a bus window; a session with the school psychologist in which he admits he wanted to punch a student but hit the window instead; and a heroic account he tells Ashley about defending a student with a disability. Each version layers over the last without resolving the truth.

After his suspension, Kyle calls Ashley. She admits she initially believed the theft rumors, and Kyle is hurt. She accepts his account and pivots to discussing her job interview at the Piercing Point, an ear-piercing kiosk at the mall. Kyle reflects on how they grew close as lab partners in ninth grade. He has never wanted to be with someone more, yet he holds back, telling himself the right moment is coming.

Back at school, Kyle encounters Zack McDade, a new student who introduces himself with theatrical flair and reveals he has read Kyle's confidential file in the principal's office. Kyle refuses Zack's handshake but finds himself intrigued. Zack soon disrupts Ms. Casey's English class during a reading of Romeo and Juliet by loudly identifying sexual innuendo in the text. As he leaves, Zack gives Kyle a nod; Kyle nods back.

Days later, Jake and teammates corner Kyle in the locker room. Zack appears atop the lockers with his cell phone, announcing he has filmed the ambush and will send it to the principal if anything happens to Kyle or himself. Jake retreats. The act binds them: Kyle now feels obligated to Zack.

Kyle's home life is strained. His mother cycles through lectures about jobs and grades; his father communicates through confiscated electronics and curt commands. One night, Kyle overhears his five-year-old sister, Paige, tell their mother she wants to be like Kyle. His mother replies that one Kyle "is enough," devastating him.

Zack invites Kyle to a party attended by friends from Crestwood Academy, a private school across town. Near midnight, Zack publicly reveals that his girlfriend, Brooke, has been writing about purging after meals. Brooke flees in tears. Kyle resolves to distance himself from Zack. At the mall, he visits Ashley at work and decides to ask her out, but a customer interrupts and the moment evaporates. Furious, Kyle shatters a paper-towel dispenser in a restroom, one in a pattern of violent outbursts he cannot control.

A confrontation at a convenience store fractures Kyle's friend group when Ryan—another hoodie—and Max flee at Jake's arrival while Kyle stands alone. Kyle walks away from the hoodies for the first time. Later, Zack invites him to break into Midlands High during Thanksgiving break. Zack has disabled window locks and knows the alarm code. Moving through the darkened hallways, Kyle feels something unexpected: For the first time, he feels welcome in the school. They pry open Jake's locker and Kyle urinates inside. On the way out, Zack asks if Ashley is Kyle's girlfriend. Kyle denies it. Zack asks if Kyle would mind if he called her, and Kyle, suppressing his feelings, tells him to do whatever he wants.

Kyle's trajectory declines further. He fails a quiz while Zack earns a perfect score. His history teacher tells him his average cannot reach the passing threshold. He interviews at Sears, where the manager is impressed by his honesty and all but offers him the job. Nicole, one of Zack's acquaintances, warns Kyle that Zack finds everyone's weakness and pushes until they break. Kyle believes he is immune.

Everything collapses on a single Tuesday. The gym coach, whom Zack has told that Kyle sells drugs, glares at him with disgust; the one adult who believed Kyle now suspects the worst. Security guards search only Kyle's locker. A voicemail from Ashley says she loves him, then clarifies she means as her best friend, and reveals that Zack asked her to skip school. Another voicemail from Zack invites Kyle to the school at nine.

Kyle enters through the French classroom window that night. Zack waits by the trophy case. He reveals he took the Sears job, confirms he triggered the locker search by telling the coach Kyle was selling drugs, and hints that something has been planted in Kyle's gym locker. He describes Ashley in crude terms, claiming they slept together and that he told Ashley Kyle was questioning his sexuality and found her unattractive. Then Zack directs Kyle's gaze into the trophy case, where a red thong hangs from a championship trophy with a tag reading "PROPERTY OF ASHLEY BIANCHI." Kyle imagines Ashley's humiliation the next morning. Instead of punching Zack, Kyle drives his fist through the glass and grabs the thong, determined to protect her. He resolves to finally tell Ashley how he feels.

Then he sees the blood. A shard has sliced his arm from wrist to armpit. The narrative circles back to the opening: Kyle stares at the blood while Zack stands white-faced, screaming, unheard in the empty school. Kyle searches for the moment everything went wrong and concludes again that it started before tenth grade. The novel ends here, its circular structure complete: the same image of blood and shattered glass that opened the story now closes it, the accumulation of Kyle's choices and refusals to choose having brought him to this moment of severe injury as the book's final question—when did it go wrong?—goes unanswered.