This Side of Paradise by F. Scott Fitzgerald, 1920

Amory Blaine learns unhelpful and unsustainable social skills from his mother, then goes into the world: to the east coast for prep school, Princeton, and adulthood. Not much happens in prep school until he, as a senior, has a turn at that most useless of social heroes, the star quarterback. Early on he makes an adult friend who could be a guide, but the monsignor seems too subtle by half for a clot like Amory. Princeton is mostly about the friends he makes, although it lets him develop a taste for theatricals (the lead up to his crash and burn is presented as a play script). Women are met along the way, but as the women get older they get better at dealing with men like him, and the damage gets worse on each successive unsuccessful encounter. His adulthood starts at advertising agency, but doesn't survive his crash and burn. World War I happens. The story ends with Amory making a pilgrimage from New York back to Princeton, during which he has an embarrassing undergraduate dorm-room bull session about socialism in the back of a chauffeured limousine, exactly the kind of pilgrimage Amory would expect to have.

This book is credited with founding the Jazz Age, but I'm skeptical. I suspect the Jazz Age got going on the backs of the oppressed, juiced by economic delirium. This book is not that story. This is the story of a spoiled (in many ways) boy stumbling around places where he doesn't belong, isn't accepted, and is unequipped to find his way in. It's a story that gets told over and over as the American bourgeois gets rolling, and Fitzgerald had the luck to be in on the leading edge.