Looking For Alaska starts by Miles Halter (later to be known as 'Pudge') attending Culver Creek Boarding School. He is introduced to his new roommate Chip "The Colonel" Martin, and he later indroduces Pudge to a girl that lives down the hall, who goes by the name Alaska Young.
After Pudge has settled in to his new boarding school, he has begun to spend more time with Alaska. Although they haven't known each other for long, he is convinced that he has fallen in love with her. Pudge learns that she has a traumatic past and just as they begin to connect on a deeper level, he is told that she has a boyfriend.
Some of Pudge's friends (including The Colonel, Takumi Lara and Alaska) plan to prank the school's wealthy students as they are all visiting their families during this time. They send out fake progress reports (which include plenty of failing grades) and sneak into their dorm rooms to put industrial blue dye in their shampoo and conditioner. After the prank is completed, they learn that Alaska's mother died infront of her when she was eight years old, and her father has never forgiven her for not trying to save her.
The next night, The Colonel, Alaska and Pudge are in Alaska's room drinking. Pudge isn't the biggest fan of this so he was the only one who wasn't visibly intoxicated. They all start playing a game of Truth or Dare and Alaska dares Miles to kiss her, and he does. They are interupted when the payphone in the hall rings. She comes back into the room after answering the phone sobbing.
Alaska leaves in her car after saying that she couldn't be here anymore to Pudge and The Colonel, they help her leave because she is hysterical despite the fact that she is heavily under the influence of alcohol. They immediately regret not stopping her or asking where she was going and why.