This Side of Paradise (1920) is a novel by F. Scott Fitzgerald. It was Fitzgerald’s first novel and became an instant hit, launching Fitzgerald into literary fame for its social commentary on a younger generation fueled by indulgence and materialism. This Side of Paradise is also a historical depiction of the Jazz Age, like Fitzgerald’s most famous novel, The Great Gatsby.

This Side of Paradise follows Amory Blaine’s coming of age during prep school and four years at Princeton. Over time, Amory loses his romantic outlook on life and matures into a man who views the world through a lens of disappointment and disillusionment. Fitzgerald uses Amory’s development to discuss love and money’s impact on relationships while also exposing the dark side of the Jazz Age.

This guide refers to the 1995 Scribner Paperback Fiction paperback edition.

Content Warning: The source text discusses attempted death by suicide.

Plot Summary

In Book 1, Amory Blaine spends much of his childhood traveling the country with his mother, Beatrice. At 13, Amory lives with his aunt and uncle in Minneapolis for two years. He attends school there and has difficulty getting along with the other students, who find him snobbish and arrogant. When Amory returns home to Lake Geneva, he begs Beatrice to send him away for preparatory school. Beatrice agrees, so Amory goes to St. Regis’, a boarding school in Connecticut. Before school begins, he visits Monsignor Darcy, one of his mother’s friends. The two quickly develop a deep friendship, and Darcy becomes a mentor to Amory for the remainder of the novel. Amory also struggles at St. Regis’ because he doesn’t relate well to the other students. However, his second year is better because he becomes a football star and focuses on becoming popular and adaptable in his behavior.

After he graduates from prep school, Amory attends Princeton University in New Jersey. He continues to feel a sense of superiority over his peers, yet he makes deep and lasting friendships with his housemates and classmates. Some of his friends include Tom D’Invilliers, Kerry and Burne Holiday, and Alec Connage. These characters have a significant impact on the man Amory becomes. He also begins experiencing romantic relationships, first with Isabelle Borgé, a beautiful yet shallow debutante from Minneapolis. The couple dates during the spring of Amory’s second year at Princeton, to the detriment of his academic performance. He feels that this is the happiest time of his life as he moves from party to party with his friends and Isabelle, having reached his goal of climbing to the top of the Princeton social class. Close to summer vacation, classmate Dick Humbird dies in a car accident, significantly impacting Amory, who greatly admired the young man. Amory visits Isabelle’s summer home when school ends, but once there, he quickly learns he has no genuine affection for her. He ends the relationship and returns to Princeton.

At the start of Amory’s third year, he takes an exam to compensate for his poor performance the previous spring. He fails the exam and must resign from his various clubs and committees, thus ending his popularity streak. Amory’s father dies, but Amory’s only concern is the family’s financial status. Beatrice reassures him that they’ll be okay if they live frugally. During his senior year, Amory becomes close to Burne Holiday; Kerry has left Princeton and joined the army, allowing Amory to get to know his brother better. Amory also enlists in the military to fight in World War I. As he prepares to go to Europe, Amory learns of Beatrice’s death and knows he’s now destitute. He also learns of Kerry’s and another friend’s death in the war.

In Book 2, Amory returns home from Europe a changed man. He moves into a New York apartment with Alec and Tom and falls in love with Rosalind Connage, Alec’s sister. The couple falls in love and considers marriage. However, Rosalind comes from a wealthy family and does not want to leave her accustomed comfort: She breaks her engagement because Amory lacks money and turns to the wealthy Dawson Ryder instead. Amory never recovers from the heartbreak he suffers from Rosalind’s decision. He knows he’ll never succeed in love and no longer feels joy or happiness. Alec moves out of their New York apartment to live with his family, but Amory and Tom remain.

When Amory visits an uncle in Maryland, he meets Eleanor Savage, an intelligent woman who shares Amory’s love for poetry and literature. They have deep and meaningful conversations, and while the couple appears perfect for each other, Amory can’t commit to her and ultimately leaves after she attempts suicide. Amory then goes to Atlantic City, where he runs into Alec. Amory ends up sacrificing his reputation to save Alec’s when Alec brings an unmarried woman into the hotel with him. Amory makes the sacrifice knowing that Alec has a family who will be devastated by the news, whereas Amory has no one who will be affected by it. He returns to New York and learns of Rosalind’s engagement to Dawson Ryder. Now that he knows Rosalind is truly out of reach, he can move on and stop pining for her.

A penniless Amory stands outside a theater and realizes how much he detests poor people, which is ironic because he is now part of the lower class. He decides to walk to Princeton and meets a former classmate’s father on the way. Amory discusses wealth, class, and what it means to be spiritually married and unmarried. The novel concludes with Amory returning to Princeton’s campus, feeling nostalgia for his youth but realizing that he knows himself and nothing more.