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.
—F. Scott Fitzgerald, This Side of Paradise (1920)[18]
Amory Blaine, a young Midwesterner, is convinced that he has an exceptionally promising future. He attends a posh college-preparatory school and later Princeton University. He grows estranged from his eccentric mother Beatrice and becomes the protégé of Monsignor Thayer Darcy, a Catholic priest. During his sophomore year at Princeton, he returns to Minneapolis over Christmas break and encounters Isabelle Borgé, a wealthy, young debutante whom he first met as a boy. They embark upon a romantic relationship.
While at Princeton, he deluges Isabelle with letters and poems, but she becomes disenchanted with him due to his incessant criticism. After his prom, they break up on Long Island. Following their separation, Amory graduates from his alma mater and enlists in the United States Army amid World War I.[a] He is shipped overseas to serve in the trenches of the Western front.[b] While overseas, he learns his mother Beatrice has died and most of his family's wealth has been lost due to a series of failed investments.
After the armistice with Imperial Germany, Amory settles in New York City as it undergoes the birth pangs of the Jazz Age.[c] He becomes infatuated with a cruel and narcissistic flapper named Rosalind Connage. Desperate for a job, Amory is hired by an advertising agency, but he detests the work.[d] Due to his poverty, his relationship with Rosalind deteriorates as she prefers a rival suitor, Dawson Ryder, a man of wealth and status. A distraught Amory quits his job and goes on an alcoholic bender for three weeks until the start of prohibition in the United States.
F. Scott Fitzgerald among junior classmen at Princeton University in 1917. Fitzgerald is pictured in the top row, third from the left.When Amory travels to visit an uncle in Maryland, he meets Eleanor Savage, an 18-year-old atheist. Eleanor chafes under the religious conformity and gender limitations imposed on her by contemporary society in Wilsonian America. Amory and Eleanor spend a lazy summer conversing about their love. On their final night together before Amory must return to New York City, Eleanor attempts suicide in order to prove her disbelief in any deity, and Amory realizes that he does not love her.
Returning to New York, Amory learns that the fickle Rosalind is engaged to be married to his affluent rival Dawson Ryder. A devastated Amory is further dispirited to learn that his beloved mentor Monsignor Darcy has died. Homeless, Amory wanders from New York City to his alma mater Princeton and, accepting a car ride from a wealthy man driven by a resentful chauffeur, he speaks out in favor of socialism—although he admits he is still formulating his thoughts as he is talking.
Concluding his long argument about their time's political and societal problems, Amory emphasizes his disillusionment with the current era. He announces his hope to stand alongside those who would bring forth fundamental changes to the age. The men in the car denounce his views, but upon learning that one of them was the father to one of his old friends at Princeton and that the son had died in World War I, Amory and the man reconcile, acknowledging mutual respect. It dawns on Amory that his time as a young promising Princetonian man has all been but a wasted dream, and he parts ways with his travel mates amicably.
Continuing his lonesome walk towards Princeton, Amory gradually forsakes the final obsessions about times and people that once constituted fundamental ideologies of his old self. Standing alone and musing at the sight of Princeton's gothic towers, Amory ecstatically yet somberly concludes: "I know myself . . . but that is all."[24]
