Miles Halter, a teenage boy obsessed with last words, leaves his normal 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". Miles' new roommate, Chip "The Colonel" Martin, nicknames Miles "Pudge" and introduces Pudge to his friends: hip-hop emcee Takumi Hikohito and Alaska Young, a beautiful but 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!" 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. 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. Alaska and Pudge grow closer and he begins to fall in love with her, although she insists on keeping their relationship platonic because she has a boyfriend at Vanderbilt University who she insists she loves.