Looking for Alaska tells the story of Miles “Pudge” Halter, a high school junior who divides his life into time before and time after a life-changing event that the reader will not discover until later in the novel.

Miles plans to attend the Culver Creek boarding school for his junior year of high school. Although his parents worry that Miles wants to attend the school because he does not have friends at his current school, Miles reveals that he is actually influenced by the last words of the poet François Rabelais about “seeking the Great Perhaps.” He moves to Birmingham, Alabama to attend Culver Creek and becomes friends with his roommate, Chip “The Colonel” Martin. Chip teaches Miles about the social structure of the school. He explains that the wealthy students that go home to their parents’ mansions every weekend (the “Weekday Warriors”) do not get along with his friend group.

Chip introduces Miles to his friend Alaska, and Miles is quickly enamored by her. While Miles is obsessed with people’s final words and wants to seek François Rabelais’s “Great Perhaps,” Alaska enjoys books and wants to know the nature of “the labyrinth of suffering” that Simón Bolívar evoked in his final words.

The Weekday Warriors sneak into Chip and Miles’s dorm on Miles’s first night and throw Miles into the lake with his limbs bound by tape. Chip and Miles discover that this action was taken in retaliation for Chip supposedly ratting out their friends—a couple named Marya and Paul—and getting them expelled the previous year. Miles, Chip, Alaska, and another friend, Takumi, begin planning a revenge prank. Miles becomes part of their friend group and starts smoking cigarettes. The four of them get caught smoking and Alaska and Chip cover for Miles and Takumi, demonstrating to Miles that you cover for your friends instead of ratting them out.

Lara joins Alaska, Chip, Takumi, and Miles as they execute their revenge prank on the Weekday Warriors. They set off fireworks and put dye in the Weekday Warriors’ hair products. They also get on the computer of the Dean (whom they call “the Eagle”) to send bad grade reports to the parents of the Weekday Warriors. The five of them spend the remainder of the night and weekend camping and hiding in a barn on campus as their alibi is that they were all off campus. They play a drinking game and Alaska reveals that, as a child, she saw her mom die of an aneurysm and did not call an ambulance because she thought her mom was just sleeping. When they quit playing the drinking game, Miles kisses Lara. He asks if she wants to be his girlfriend and she says yes.