Course Hero. "This Side of Paradise Study Guide." Course Hero. 13 Mar. 2017. Web. 15 Oct. 2018. <https://www.coursehero.com/lit/This-Side-of-Paradise/>.
Course Hero. (2017, March 13). This Side of Paradise Study Guide. In Course Hero. Retrieved October 15, 2018, from https://www.coursehero.com/lit/This-Side-of-Paradise/
(Course Hero, 2017)
Course Hero. "This Side of Paradise Study Guide." March 13, 2017. Accessed October 15, 2018. https://www.coursehero.com/lit/This-Side-of-Paradise/.
Course Hero, "This Side of Paradise Study Guide," March 13, 2017, accessed October 15, 2018, https://www.coursehero.com/lit/This-Side-of-Paradise/.
For Amory, New York City is a symbol of everything cosmopolitan and adult. Given its proximity to Princeton University (where he attends college), he and his friends spend a great deal of time there, cavorting and drinking. Initially, the city holds a great deal of promise for him, but after an episode there in which he hallucinates seeing the devil, it shows a darker, more sinister side.
When Amory ultimately moves to New York City with his Princeton friend, Thomas, the city again symbolizes the promise of a successful life. He falls in love with Rosalind Connage, gets a job, and plans to marry her. But his time in New York is marked by his breakup with Rosalind and its aftermath, the loss of his job and remaining family money, and the death of his friend, Monsignor Darcy. These events leave Amory penniless and alone, wandering a city that has become a much darker, sadder place for him. In this way, New York City acts as a crucible, a place in which Amory undergoes a transformation. His experiences there cause him to reconsider who he is and what he believes about the world.
In Book 1, Chapter 1, Amory and his school friend come up with the idea of the "slicker" versus the "big man" in order to decide their trajectory in the world. They define the slicker as someone who has "a clever sense of social values," dresses well, shines in his chosen activities, and is ultimately successful "in a worldly way." The big man, on the other hand, is superficial and stupid, which results in a problematic future in which he "feels lost without his circle, and always says that school days were happiest, after all."
For Amory, being a slicker is the only real goal in life, and one that he keeps in mind as a guidepost for much of his adolescence. In college, he privately revises the definition, adding "courage and tremendous brains and talents," as well as a "bizarre streak" for the fun of it. Amory indeed possesses some of the characteristics of the slicker, but in the end he fails to be successful in the world. The fact that Amory believes there are only two identities to choose from that oppose each other (as winner versus loser) symbolizes both his intense desire to be successful and impress others but also how limited his formula for doing so really is.
Drinking plays a large role in the lives of Amory and his friends, symbolizing distraction and self-destruction. Amory's friend, Dick Humbird, for example, is killed in a car accident after a night of drinking. This doesn't stop Amory and his friends from continuing to get in trouble by staying out late drinking at bars and clubs themselves. Drinking fuels the rebelliousness and freedom of the young men and women in the novel, but it often serves as a distraction from painful realities as well.
Amory turns to alcohol after he has his heart broken by Rosalind. He drinks so heavily that he gets into trouble, blacking out in one instance and being beaten up badly in another. This self-destructive bender is only cut short after Prohibition laws take effect, which forbid the sale of liquor. Amory doesn't regret his binge, but he doesn't long to continue it, either.