This Side of Paradise by F. Scott Fitzgerald

This Side of Paradise isn't regarded as one of Fitzgerald's best books but it was published bang on 1920, marking the beginning of his fascination with the on-coming Jazz Age. It's semi-autobiographical and details his experiences of elite social circles at Princeton University. It made him famous overnight.

Fitzgerald dropped out of Princeton and began writing this book, plus also serving in the war. He initially wanted to call it The Romantic Egotist but it was rejected by publishers left, right and centre. Whilst living in St. Paul, Minnesota, Fiztgerald would rework the book to incorporate details of his personal life, including his romantic disappointments and social ambitions unfulfilled. It was then accepted for publication by Charles Scribner's Sons thanks to an editor by the name of Maxwell Perkins - a man who recognised the potential of the author to detail the highs and lows of the following decade.

It was published at a transitioning time for America. It was no longer the conservative Victorian era anymore and more young people were embracing a more liberal attitude towards morality and love. The Side of Paradise attempts to capture this same energy of post-war uncertainty and thus, makes for it becoming one of the defining books for the beginning of a whole new generation.

Upon publication, the book was a runaway success, selling out its first printing in three days. It made Fitzgerald an instant celebrity and secured his literary career. Crucially, the novel’s success reignited his courtship with one Zelda Sayre, who had previously rejected him due to his lack of financial stability. With his newfound success, Zelda agreed to marry him, and they became the defining couple of the Jazz Age. Though the book still details how he, his wife and a bunch of other young people of the decade would come to be known as the 'Lost Generation'...

Plot

The novel follows Amory Blaine, a handsome, intelligent, and self-absorbed young man who embarks on a journey of romantic idealism, intellectual awakening, and ultimate disillusionment. Amory, raised by his eccentric and socially ambitious mother, Beatrice, grows up believing himself to be destined for greatness. He attends St. Regis School, where he develops a sense of superiority, and later enrolls at Princeton University, where he becomes deeply involved in literature, philosophy, and social climbing. However, he remains fundamentally restless and struggles to find his true purpose.

At Princeton, Amory falls in love with Isabelle Borgé, a beautiful but shallow young woman. Their relationship is passionate but ultimately unfulfilling, as Isabelle does not share Amory’s idealistic notions of love. Heartbroken, he immerses himself in intellectual pursuits but remains haunted by his inability to reconcile reality with his romantic ideals.

World War I interrupts his education, and Amory enlists in the army, though he never sees combat. Upon returning, he becomes deeply disillusioned with the materialistic society around him. His search for meaning leads him into another tumultuous romance, this time with Rosalind Connage, a charming and sophisticated debutante. Rosalind, however, ultimately chooses to marry a wealthy man instead, rejecting Amory due to his lack of financial stability.

This second heartbreak plunges Amory into philosophical despair, and he turns to books, political ideas, and introspection in an attempt to make sense of his failures. He experiments with socialism, discusses existential questions with friends, and begins to reject the aristocratic values he once admired.

The novel concludes with Amory walking alone along a road, having lost his romantic illusions, his financial security, and his youthful confidence. He reflects on his experiences and famously declares, "I know myself, but that is all." This final statement signals both a personal revelation and an existential resignation, as he realises that self-awareness alone does not guarantee happiness or success.

Into the Book

Restlessness and Disillusionment:

Throughout the novel, Amory represents the restlessness and disillusionment of the post-war generation. Initially, he believes in romantic love, intellectual superiority, and personal destiny, but each of these ideals is shattered by reality.

His first heartbreak, his war experience, and his rejection by Rosalind force him to confront the emptiness of his ambitions. Fitzgerald repeatedly contrasts youthful idealism with harsh reality, showing how Amory’s romantic dreams inevitably crumble.

By the end, Amory has lost everything such as: his wealth, his friends, and his illusions, but gains self-awareness. However, Fitzgerald leaves it ambiguous whether this self-awareness leads to personal growth or deeper cynicism.

"I'm not sentimental—I'm as romantic as you are. The idea, you know, is that the sentimental person thinks things will last—the romantic person has a desperate confidence that they won't."

- This Side of Paradise by F. Scott Fitzgerald

Class and Social Status:

Amory's aspirations are deeply tied to class and social status. Raised with the belief that he is destined for elite society, he spends much of his youth attempting to climb the social ladder. However, Fitzgerald critiques the inherent superficiality of the American aristocracy, showing how wealth dictates relationships, marriages, and opportunities. Rosalind’s decision to marry a wealthy man instead of Amory highlights the economic determinism of the era.

Amory’s financial downfall forces him to reevaluate his beliefs, leading him towards a brief flirtation with socialism. However, his engagement with leftist politics remains largely theoretical, reflecting Fitzgerald’s own ambivalence toward radical social change.

"She wanted, it seemed, the old things, money and position, admiration and beaux."

- This Side of Paradise by F. Scott Fitzgerald

The Bildungsroman:

The novel is ultimately a bildungsroman, charting Amory’s struggle to define himself. From Princeton to his failed romances, from war to personal loss, each experience strips away a layer of his identity, leaving him in an existential crisis. Amory frequently engages in philosophical debates, reflecting his desire to find a greater meaning in life. Yet, by the end, he is left with only self-knowledge, rather than a concrete purpose.

The final line encapsulates both Amory’s growth and his uncertainty, as he realises that self-awareness does not necessarily lead to happiness or success. Fitzgerald, through Amory, captures the broader existential anxiety of the Lost Generation.

"I know myself, but that is all."

- This Side of Paradise by F. Scott Fitzgerald

Why It's a Masterpiece

Apart from the disillusionment and youthful change that came along with this age, Fitzgerald is really credited here with basically writing the first book documenting a story to do with that generation. It bases itself in a newer experimental style as well, reflecting a rejection of older more Victorian maxims of literature. For example: the book takes on a more stream-of-consciousness form - something made famous by folks like Virginia Woolf and others. This would make it one of the first truly modernist books of its kind in America.

It also became a masterpiece because of its outer-world. The exploration of what we call 'celebrity' is something to pay attention to as Fitzgerald became the poster-boy for his generation overnight. It was a book that would come to influence later Lost Generation writers like Hemingway and Faulkner, who would both adopt their own modernist writing styles. But it also brought the more Victorian-based bildungsroman into the 20th century by focusing on more modern issues of love, philosophy and existential crises.

Conclusion

I personally enjoyed this book's exploration of youth, love and self-discovery because it is so timeless. It can literally be applied to my own generation as well. Those who go off to university in search of themselves but just end up with nothing. If anything, we are the Lost Generation of the 21st century. We are all F. Scott Fitzgerald.

Next Week: The Ragged-Trousered Philanthropists by Robert Noonan