This article intents to discuss the loneliness that haunts the Glass family. Loneliness that appeared as ills of modern society was relevant to the problems of individualism and isolationism that supplanted the optimistic transcendental concept that solitude is a way to concentration on one’s inner self that affirms the divinity of man. Salinger anticipates the sociologist Philip Slater who condemns American obsessions with privacy in his book The Pursuit of Loneliness (1970). Saymour Glass and Franny Glass were beset with an existential crisis. The pressure of conformity prevailed against the autonomy that is to retain the freedom to define one’s own path. Salinger create a sense of entrapment of futility on characters caught in webs of circumstance. For them, humans are isolated from each other, having links and being led by a blind-selfish inner will. In order to escape the blind will, they either withdraw into artistic or religious contemplation, trying to appease one’s innate thirst for recognition, credit, and most importantly, “the will to live”. They mixed up the personal self, possibly inaccessible to anyone else, with his own life-path that largely depends on his own moves. They observed and evaluated everything that is around them, and hesitated. They tried to break the deadlock by intensive reading of Eastern philosophies, existential philosophy, Japanese haiku and Chinese literary works. However, it proves that the more they read, the longer they wait. The inner landscape might be hidden from fellow human beings, but to wait and only waiting is a tragic error.