The film, inspired by real events, begins with Tobias "Toby" Hammel (portrayed by Thomas Mann) at an airport, as he gazes at a beautiful girl on the escalator. As he narrates, he introduces himself with a shocking admission: "My name is Toby: I'm seventeen years old. I'm a scholarship winner, and I've started and run an international drug ring. And I am fucked."
Three months earlier, we see Toby arriving on the campus of Sage Hall in September 1984. He feels out of place among the affluent students, whom he refers to as "preppies," believing they have their futures handed to them due to their wealth and connections. At home, his mother, Ingrid (played by Amy Hargreaves), soon reveals that Toby has been awarded a scholarship to attend the prestigious school, a fact he finds hard to accept. Despite his family's hopeful aspirations, Toby struggles with feelings of inadequacy.
After initially skipping registration day, Toby's mother insists on taking him to complete his enrollment. However, the atmosphere at the school proves to be overwhelming, especially during the opening ceremony, where he suffers a humiliating mishap while signing the honor code. In this moment of vulnerability, he meets Fidel (played by Guillermo Arribas), who understands Toby’s outsider status and offers support.
Toby's life at school is tumultuous, marked by bullying and the efforts of his peers to ostracize him. After forming a bond with Fidel, he becomes infatuated with Alex Hayes (played by Lucy Fry), who initially seems unattainable. The dynamics shift when Alex asks Toby to procure marijuana. He and his friend Dennis (played by Dylan Blue) scramble to find a dealer, leading Toby down a dangerous path. Their night of searching ends badly for Toby, leading to his suspension after being caught with the drug.
Upon returning to Sage Hall, Toby’s reputation transforms as the story of the pot incident circulates, leading to newfound acceptance among his wealthier peers, including Alex. He becomes entangled in their world, sharing in their indulgences, which include drugs. However, the pressure mounts, and when his home life and feelings of not belonging become unbearable, Toby seeks ways to keep up with his peers, even as he begins dealing drugs to fit in.
In pursuit of acceptance, Toby travels to Colombia with Fidel, diving deeper into the dangerous drug culture that fuels his new-found popularity. Awash in the thrill of making deals, he finds himself entwined with dangerous characters, leading to romantic encounters with Alex that escalate as they cross boundaries that threaten to unravel everything he’s worked towards.
Toby’s actions culminate in a fateful trip back, where he makes the harrowing decision not to dispose of the drugs he brings. This choice leads to his arrest, causing a rift between him and Alex. As the weight of his actions bears down, friendships fracture and tragic events unfold, including the devastating suicide of Laura, a girl who had been part of their circle.
In the courtroom, Toby faces the consequences of his choices, grappling with the fallout for his family, friends, and the relationships he cherished. As he contemplates his fate, he acknowledges the pain this has caused his parents, especially his mother’s heartbreak. The narrative concludes with a glimpse of reality, depicting the aftermath of the events, focusing on Toby's transformation from an outsider to a prisoner, intertwined with the lives he impacted along the way.
As the credits roll, viewers are left with the sobering truth of Toby’s story, reminding us of the impact decisions make on lives and the struggle for acceptance amidst a world steeped in privilege and expectation.
