Miles Halter, a sixteen-year-old with a fascination for last words, begins his scholastic adventure at Culver Creek boarding school in Alabama with an introduction to his roommate Chip "Colonel" Martin, a trailer-bred genius. Chip nicknames the skinny Miles "Pudge" and introduces him to Alaska Young, a beautiful, literate and intellectually gifted teenager with a head full of elaborate pranks. Under the tutelage of his new (and real) friends, Miles learns to drink, smoke, escape punishment, and understand people. A few days following a major, adrenaline-pumping prank, Alaska drives insanely drunk, crashes her car and dies instantly.
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Miles and Chip, both grieving for their lost friend, wondering if she committed suicide or was killed accidentally, search for evidence of the reasons behind her death. They also feel guilty because they were the last people to see her alive and did not stop her from driving drunk. From his experiences with this loss, Miles learns valuable lessons about loyalty, friendship, and life.
The novel is divided into two sections: "before" and "after". Miles' school year is comprised of exactly 136 days before and after Alaska's death.