Its protagonist, Amory Blaine, is a handsome middle-class student at Princeton University who dabbles in literature and engages in a series of unfulfilling romances with young women.

Fitzgerald, who took inspiration for the title from a line in Rupert Brooke's poem Tiare Tahiti,[1] spent years revising the novel before Charles Scribner's Sons accepted it for publication.

[7][8] His newfound fame enabled him to earn higher rates for his short stories,[9] and his improved financial prospects persuaded his fiancée Zelda Sayre to marry him.

[21][22] The novel created the widespread perception of Fitzgerald as a libertine chronicler of rebellious youth and proselytizer of Jazz Age hedonism which led reactionary societal figures to denounce the author and his work.

Accepting a car ride from a wealthy upper-class man driven by his working-class chauffeur in a Locomobile, Amory speaks out in favor of socialism in the United States—although he admits he is still formulating his thoughts as he is talking.

[73][74] During his sophomore year at Princeton, Fitzgerald returned home to Saint Paul, Minnesota during Christmas break where the 18-year-old aspiring writer fell in love with 16-year-old Chicago debutante Ginevra King.

[80][81] In November 1917, hoping to have a novel published before his deployment to Europe and his anticipated death in the trenches of World War I,[81] Fitzgerald began writing a 120,000-word manuscript titled The Romantic Egotist.

[100] In October 1918, Fitzgerald submitted a revised version of The Romantic Egoist to Scribner's, but the publisher rejected the work a second time, and he captioned their telegram in his scrapbook: "The end of a dream.

[118] Abstaining from alcohol,[117] he worked day and night to revise The Romantic Egotist as This Side of Paradise—an autobiographical account of his Princeton years and his romances with Ginevra King, Zelda Sayre, and other young women.

"[86] Despite the fact that Fitzgerald's manuscript repelled older employees at Scribner's, the executives relented out of fear of losing Perkins as a gifted editor and literary talent scout.

[125] "The postman rang, and that day I quit work and ran along the streets, stopping automobiles to tell friends and acquaintances about it⁠—my novel This Side of Paradise was accepted for publication," he recalled, "I paid off my terrible small debts, bought a suit, and woke up every morning with a world of ineffable top-loftiness and promise.

[132] Although Fitzgerald complained to his friend Burton Rascoe that This Side of Paradise didn't make him wealthy,[5] his new fame enabled him to earn much higher rates for his short stories,[9] and Zelda resumed their engagement as he could now afford her privileged lifestyle.

[135][136][137] Despite his disappointing marriage, Fitzgerald had achieved the peak of his fame and cultural salience, and he recalled traveling in a taxi one afternoon through the streets of New York City and weeping when he realized he that he would never be as happy again.

[138] This Side of Paradise was the flaming skyrocket of its season... [Fitzgerald's] photograph appeared in all of the exclusive journals as the picture of the hope of young America, the first person to turn the spotlight on the flapper in the back seat on a lonely road...

[8][141][22] He riveted the public's attention on the promiscuous activities of their sons and daughters cavorting in the rumble seats of Bearcat roadsters and prompted a national conversation over the perceived immorality of this hedonistic younger generation.

[11][145] According to writer John O'Hara, half a million young men and women "fell in love with the book,"[59] and, according to essayist Glenway Wescott, Fitgerald's novel became the rallying banner of the "youth movement".

'"[12] Such articles fostered the widespread impression of Fitzgerald as championing the revolt by young Americans against traditional norms and as the outstanding aggressor in the rebellion of "flaming youth" against the "old guard".

[150] Declaring that World War I "had little or nothing to do" with the change in morals among young Americans and did not leave "any real lasting effect,"[150][151] Fitzgerald attributed the sexual revolution among youth to a combination of popular literature by H. G. Wells and other intellectuals criticizing repressive social norms, Sigmund Freud's sexual theories gaining salience, and the invention of the automobile allowing youths to escape parental surveillance in order to engage in premarital sex.

Heywood Broun decried Fitzgerald's use of modern slang and attempted to discredit him by claiming the author fabricated his novel's depiction of young people engaging in drunken sprees and premarital sex.

The young American novelist usually reveals himself as a naive, sentimental and somewhat disgusting ignoramus—a believer in Great Causes, a snuffler and eye-roller, a spouter of stale philosophies out of Kensington drawing rooms, the doggeries of French hack-drivers, and the lower floor of the Munich Hofbräuhaus... Fitzgerald is nothing of the sort.

[173] Fitzgerald's novel soon attracted the attention and displeasure of John Grier Hibben, a Presbyterian minister and educational reformer who succeeded Woodrow Wilson as the president of Princeton University.

It would be an overwhelming grief to me, in the midst of my work here and my love for Princeton's young men, should I feel that we have nothing to offer but the outgrown symbols and shells of a past whose reality has long since disappeared.

In response to Hibben's chastising letter, Fitzgerald wrote a respectful but uncompromising reply that denied any attempt to disparage Princeton and defended his novel's depiction of the university.

[169] Although undergraduates across the country touted the novel as a realistic portrayal of college life,[146][59] Princeton alumni and former classmates continued to treat the author with contempt in social settings over the ensuing months.

After a 44-year-old Fitzgerald died of a heart attack due to occlusive coronary arteriosclerosis in December 1940, many Princeton staff and alumni continued to privately and publicly belittle the author and his literary oeuvre.

[189] Believing that prose had a basis in lyric verse,[190] Fitzgerald crafted his sentences by ear and, consequently, This Side of Paradise contains numerous malapropisms and descriptive non sequiturs which annoyed readers and reviewers.

[199] Highly educated in discussing poetry and philosophy, "Eleanor not only posits her desires in juxtaposition to the lingering expectations of women in her day but also serves as soothsayer to the demands which would be placed on females".

[201][202] Within two years, in the wake of young imitators writing in more experimental styles and discarding the traditional story structure, Weaver declared Fitzgerald's influence on younger writers to be so great as to be inestimable.

[25] Writing in The New York World-Telegram, columnist Westbrook Pegler wrote that Fitzgerald's death a few weeks prior reawakened "memories of a queer bunch of undisciplined and self-indulgent brats who were determined not to pull their weight in the boat and wanted the world to drop everything and sit down and bawl with them.

"[205] Due to this widespread perception of Fitzgerald and his literary works, the Baltimore Diocese denied him a Catholic burial and refused his family permission to intern him at St. Mary's Church in Rockville, Maryland.