Looking for Alaska is exactly this. The main character, Miles- nicknamed Pudge as an irony because of his gawky build- has an obsession with last words (here's where the intellectual mentions come in). He moves to a boarding school and meets the crazy, gorgeous Alaska Young, who he instantly falls in love with. Unfourtunately for him, she has boyfriend who she's devoted to. But this doesn't stop her (along with some other unforgettable friends like Takumi and the Colonel) from catapulting Pudge into the Great Perhaps: a world filled with covert smokes, lots of booze, and well-planned pranks. When a terrible event happens, Pudge has to overcome his grief and re-examine his thoughts on one of the saddest aspects of life (that's it, no more spoilers!).
What I will say now is that if you haven't read anything by John Green, read Paper Towns. That was by far his best. Then read An Abundance of Katherines. It's still pretty good. But after reading those two, I've gotta say, this book falls a little flat. It's not that it's horrible- it isn't by a long shot. It just doesn't stand up to the other two books. The rapping scene is funny, but other than that there wasn't much hilarity. The messages were good, but without the aforementioned hilarity they feel a little heavy. I think the main problem with this book is that it's just too short. After the climactic event, there isn't a lot of time given for Pudge to puzzle through his feelings. His conclusion seems a little abrupt, because in less than half the book he goes from a blubbering mess to a person with concrete resolve who is ready to face the world. Even with this abrupt change, the book (especially after the central event) is a bit slow at times; it was easy for me to put down.
That said, this book is still worth a read because of its unique subject matter. This review may seem really negative but don't get me wrong- it's still a great book. The end was still tear-inducing and the characters were still quirky. It's just not as wonderful as John Green's other books.
If you loved this book, you'll like:
Paper Towns by John Green
An Abundance of Katherines by John Green
Saving Francesca by Melina Marchetta
Getting the Girl by Susan Juby
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