While looking for his Great Perhaps (Francois Rabelais, poet) , Miles ‘Pudge’ Halter heads to Culver Creek Boarding School when it becomes apparent to him that he won’t find his Great Perhaps at his own high school. Culver Creek is where his father attended high school, which is one of the reasons Miles decides to go.

Quickly, attending the Creek turns Pudge’s world upside down. His room mate, Chip ‘Colonel’ Martin, quickly gives him a new nickname and introduces him to Alaska Young. As teenagers often do, Pudge falls in love with Alaska basically before even learning her name.

Though, Alaska doesn’t live up to Pudge’s hopes. She’s moody, a little bitchy, and is completely comfortable being a mystery to everyone. In retrospect, she’s a teenage girl. But, Pudge doesn’t want Alaska to be like that. He wants her to be in love with him as much as he loves her, even though she has a boyfriend.

While at the Creek, the Colonel teaches Pudge a lot of important life lessons. Including, but not limited to, not ratting on anyone. Even if you don’t like them. Students at the Creek have a long history of pranking, and the Colonel and Alaska are a perfect pair. Alaska comes up with the ideas, and the Colonel meticulously plans each prank down to the second. The pair cook up a prank they call ‘Barn Night’, and it goes off without a hitch thanks to the Colonel.

But, Alaska has a dark side. She says some dark things, and finally tells the Colonel, Takumi and Pudge about some of her inner demons. When she was young, her mother died right in front of her. Instead of calling 911 like she should have, she just sat and stared at her mother’s lifeless body. She’s held onto the guilt for a long time, and seems to have zero regard for her own life as she drinks herself silly and smokes like a chimney everyday.

One day, while drinking with the Colonel and Pudge just hangs out, Alaska freaks out about something. She begs Pudge and the Colonel to help her get off campus, and drives away drunk.

The next day, the Eagle announces that Alaska Young was in a horrible accident and has died.

Pudge and the Colonel fall into a pit of depression, blaming themselves for Alaska dying. They let her go, even though they knew she was drunk. The become obsessed with finding out if Alaska killed herself, died by accident, or was killed. They are missing a big part of the puzzle for the longest time, until Takumi fills in the blank, but they come to terms with not knowing exactly how or why Alaska died.

In honour of her, they pull off the best prank in Culver Creek history at the end of the year. Pudge comes to terms with slowly forgetting Alaska, and that she helped set him on his journey to his Great Perhaps.