How It All Goes Down
Amory Blaine is a spoiled little rich kid from Minnesota whose mother constantly dotes on him. He's basically Veruca Salt, only he doesn't fall victim to a bunch of psychotic super-smart squirrels. As he grows up, Amory develops a huge ego and a shallow knowledge of the world, concerning himself more with impressing people than with actually knowing anything. But when he gets old enough to leave home, Amory learns that there's more to life than what his mother has taught him. But it's extremely tough to overcome the years of ego-inflation he's had. He can try to act modest, but being modest ain't so easy.
Despite his laziness, Amory gets good enough grades to go to Princeton for his undergraduate degree. The guy knows he's cruising through life, and it's almost as if he wants to fail so he can finally get down to thinking about what matters to him. World War I starts before he gets the chance to fail, though, and he spends the last years of his youth fighting in the trenches of Europe.
Amory is lucky enough to return from The Great War alive. But once he's back, he becomes obsessed with the question of what his larger purpose in life is. He thinks he finds his purpose when he starts going out with a beautiful girl named Rosalind. But Rosalind dumps him because he's not successful enough. This breakup seems to be the last straw for Amory, who falls into alcoholism and spends the next year or so killing himself with booze. The only thing that really saves him is the start of Prohibition, which makes alcohol illegal in the U.S.
It'll take more than Prohibition to put Amory's life back on track, but the sad thing about this book is that Fitzgerald ends it without ever giving any kind of resolution to Amory's situation. This is (most likely) because Fitzgerald wrote this book when he was twenty-three, when he was still too young to have any answers himself.