Miles Halter, a teenage boy obsessed with the last words of famous people, leaves his regular high school in Florida to attend Culver Creek Preparatory High School in Alabama for his junior year. Miles' reasoning for such a change is quoted by François Rabelais's last words: "I go to seek a Great Perhaps."[10] Miles' new roommate, Chip "The Colonel" Martin, nicknames Miles "Pudge" and introduces Pudge to his friends: hip-hop MC Takumi Hikohito and Alaska Young, an intelligent, beautiful, and emotionally unstable girl. Learning of Pudge's obsession with famous last words, Alaska informs him of Simón Bolívar's: "Damn it. How will I ever get out of this labyrinth!"[11] The two make a deal that if Pudge figures out what the labyrinth is and how to escape it, Alaska will find him a girlfriend. Later, Alaska sets Pudge up with a Romanian classmate, Lara.
Unfortunately, Pudge and Lara have a disastrous date, ending with a concussed Pudge throwing up on Lara's pants. Alaska and Pudge grow closer, and he begins to fall in love with her. However, she insists on keeping their relationship platonic because she has a boyfriend at Vanderbilt University named Jake, whom she insists that she loves.
On his first night at Culver Creek, Pudge is kidnapped, wrapped up with duct tape and thrown into a lake by the "Weekday Warriors," a group of rich schoolmates who blame the Colonel and his friends for the expulsion of their friend, Paul. Takumi claims that they are innocent because their friend Marya (Paul’s girlfriend) was also expelled during the incident. However, Alaska later admits to Miles that she had told on both Marya and Paul to the dean, Mr. Starnes, nicknamed "The Eagle", to save herself from being expelled.
The gang celebrates a successful series of pranks by drinking and partying, and an inebriated Alaska confides about her mother's death from an aneurysm when she was eight years old. Although she failed to understand it at the time, she feels guilty for not calling 911. Pudge figures that her mother's death made Alaska impulsive and rash. He concludes that the labyrinth was a person's suffering and that humans must try to find their way out. Afterward, Pudge grows closer to Lara, and they start dating. A week later, after another "celebration," an intoxicated Alaska and Pudge spend the night with each other. Soon, Alaska receives a phone call that causes her to be hysterical. Insisting that she has to leave, Alaska drives away while still drunk, and the Colonel and Pudge distract Mr. Starnes. They later learn that Alaska was driving under the influence and died.
The Colonel and Pudge are devastated, blame themselves, wonder about her reasons for undertaking the urgent drive, and even contemplate that she might have deliberately killed herself. The Colonel insists on questioning Jake, her boyfriend, but Pudge refuses, fearing that he might learn that Alaska never loved him. They argue, and the Colonel accuses Pudge of loving only an idealized Alaska he made up. Pudge realizes the truth and reconciles with the Colonel.
To celebrate Alaska's life, Pudge, the Colonel, Takumi, and Lara team up with the Weekday Warriors to hire a male stripper to speak at Culver's Speaker Day, a prank that Alaska had developed before her death. The whole school finds it hilarious; even Mr. Starnes acknowledges how clever it was. Pudge finds Alaska's copy of The General in His Labyrinth with the labyrinth quote underlined and notices the words "straight and fast" written in the margins. He remembers Alaska died on the morning after the anniversary of her mother's death and concludes that Alaska felt guilty for not visiting her mother's grave and, in her rush, might have been trying to reach the cemetery. On the last day of school, Takumi confesses in a note that he was the last person to see Alaska and let her go as well. Pudge realizes that letting her go no longer matters as much. He forgives Alaska for dying, as he knows Alaska forgives him for letting her go.
