The story begins with Sutter Keely (Miles Teller), a high school senior who finds himself in his dimly-lit bedroom, struggling to complete an overdue essay necessary for his college application. The prompt challenges him to recount a hardship he has faced and how he overcame it. Sutter's response reveals the disruption of his seemingly perfect life as the upbeat "life-of-the-party" teen following the breakup with his attractive and popular girlfriend, Cassidy. In a series of brief flashbacks, we get a glimpse of Sutter’s goofy personality—his laid-back, lampshade-wearing antics that explain his seemingly endless invitations to parties, yet highlights how little respect he garners from his peers, including Cassidy.
Eager to help a friend make a romantic connection, Sutter attempts to orchestrate a "hook-up" by using his knack for procuring alcohol to attract two beautiful girls. However, after a chaotic series of events, Cassidy confronts him at a party, accusing him of infidelity. Although the misunderstanding could be easily resolved, Cassidy moves on quickly to a new boyfriend, leaving Sutter heartbroken. In his frustration, he drives under the influence, only to wake up in an unfamiliar yard, met by the earnest Aimee (Shailene Woodley), who wakes him, concerned for his well-being. While she introduces herself, it's clear that Sutter and Aimee come from vastly different social circles. Aimee, burdened with supporting her family through her paper route—an obligation her disinterested mother shirks—declines Sutter's offer to help her out at first, only to relent when he mentions it would assist them both.
With Aimee feeling flattered by the attention from a popular kid, and Sutter keen to convince her of her own attractiveness, a bond begins to form. Despite his partying lifestyle negatively impacting his academics, he enlists Aimee’s help as a tutor, which she willingly accepts. As their relationship develops, Aimee finds herself falling for Sutter while he still clings to his past with Cassidy, failing to reciprocate Aimee's deepening affection. Despite this, he takes Aimee to various parties and their prom, hoping to inspire her to break free from her shell. Their prom night culminates in an awkward yet tender moment where Aimee loses her virginity to Sutter.
Sutter's world becomes increasingly chaotic, as his mother, working tirelessly as a nurse, neglects to address her son's spiraling behavior. Obsessed with preventing him from contacting his estranged father, a man Sutter believes his mother unjustly rid himself of, he faces emotional turmoil. When Sutter finally secures his father's number from his sister, he embarks on a four-hour drive with Aimee for support. However, their reunion with his father reveals a man who embodies each negative trait Sutter wishes to escape. Let down and seeking solace through alcohol, Sutter's reckless driving nearly results in disaster when he narrowly avoids a fatal crash after consuming large amounts of liquor.
Despite his dangerous actions, Aimee's main concern remains Sutter's well-being, professing her love for him. However, burdened by feelings of unworthiness, Sutter pushes Aimee away, leading to a tragic accident where she suffers a broken arm. This incident plunges Sutter into a deeper state of despair, causing him to further indulge in alcohol while grappling with his inability to confront his past or envision a positive future. Aimee, meanwhile, plans for a college journey to Philadelphia, hoping to share her life with Sutter as he pursues community college.
On the day of Aimee's departure, Sutter ignores her calls, reflecting a return to the opening scene where the same essay question looms large. Struggling with his self-imposed hardships, Sutter experiences a moment of clarity. Realizing he has the power to change his circumstances, he takes a leap of faith and sets out to reunite with Aimee at college, marking a pivotal moment in both their lives.
