I did not have much in common with Caufield. I have never attended or even visited a private boarding school, much less been kicked out of several as Holden had. At 15 or 16, I did not have the cash necessary to hide and entertain myself in Manhattan for three days. And I did not have the nerve to strike up conversations with strangers or attempt to buy liquor in a bar or hire a prostitute.
But something about Holden's inner monologue resonated with me. He felt alone in the world - disconnected from his surroundings. He wavered between feelings of superiority over the phonies in his life and inadequacy due to his own failings. He was intelligent, but unfocused - a classic underachiever.
Holden is an extrovert. He craves the company of others and has no trouble approaching strangers. But he is self-destructive and manages to destroy nearly every relationship in his life. Rude to nearly everyone - sometimes flying into a rage at the slightest provocation. Although his observations are often profound, their legitimacy is damaged by his focus on the negative. Haunted by the death of his brothers, he stumbles through life with no plan. The only genuine relationship he has is with his younger sister Phoebe.
Holden is far from likeable. He is too judgmental and far too cynical; but his frustration is understandable, which makes him relatable. He is the worst parts of me - judging the faults of those to whom he is attracted, but harboring resentment against himself. Holden is my feelings of alienation, angst, and insecurity that rear their ugly heads from time to time.
I felt this a lot in high school.
And now – decades later – I sometimes still fall into that same pit.