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Miles Halter leaves Florida to his new boarding school in Alabama, Culver Creek Preparatory School, searching for the "Great Perhaps." Upon his first day, he meets his new roommate Chip "THe Colonel" Martin, who gave him the nickname "Pudge" for his slender appearence. Chip introdroduced his friend Alaska Young, who he finds himself being interested in for her good looks.
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Miles gets kicked out for not paying attention in his World religion class. Alaska defends Miles by standing up for him.
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MIles, Alaska, Colonel and Takumi got caught by the Eagle for smoking. They were sent to the jury and Alaska and The Colonel took the blame for it.
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Alaska sets up a triple and a half date with Miles and Lara, Alaska and her boyfriend, The Colonel and his girlfriend, and Takumi. They go to watch a basketball game, only ending up with Miles having a concussion.
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The weekday warrior flooded Alaska's room by poking a hole through her window. Her books ended up getting wet and ruined as well.
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MIles stays at Culver Creek on Thanksgiving with Alaska.
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Alaska and friends plans on pulling a pre-prank to get back at Kevin and his friends.
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The group of friends learns about each others happiest and worst days while playing a game. During the game, Alaska revealed that that her mother died from Aneurysm. She regret not calling 911. later that night, Miles asks Lara to be his girlfriend and she agrees.
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Miles, Alaska and the Colonel plays truth or dare. Alaska dares Miles to hook up with her and the two makes out. Late at night, Alaska starts freaking out and asks to help her get out of Culver Creek.
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The Eagle asks everyone to gather in the gym. Miles and The Colonel thought they were getting in trouble for helping Alaska escape last night. The Eagle announced that Alaska has passed away last night by a car accident. Miles thinks that it's all his fault and he still doesn't accept the fact that she's dead and believes that she's playing a prank.
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Miles and The Colonel starts investigating Alaska's death. They start off by finding information at the polive station and talking to the policeman who witnessed the accident.
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Miles finds Alaska's doodled flowers on the payphone. He connects it to the flowers in the car during the accident.
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On the day of Alaska's death anniversary, Miles and The Colonel realizes that the reason Alaska was freaking out was because she almost forgot her mother's death anniversary.
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Miles reads a note from Takumi saying that he knew what happened on the day of the accident and he knew why Alaska was upset that day.