As Holden Caulfield faces his dismissal from yet another school, he battles intense feelings of isolation and loss. To fight the loneliness he experiences, Holden reaches for anyone and everyone he can. Holden turns to people he can access, not necessarily people he likes. He turns to these people because of proximity, shared history, and even just one redeeming quality. Holden behaves as though anyone he knows may suffice in his time of need. Besides the people he knows, Holden also attempts to engage people he doesn’t know. He seems equally indiscriminate with strangers. Upon his departure from the school, Pencey Prep, Holden initiates conversation with all manner of strangers: adult men at work, women at restaurants, and children at play. With all of the strangers, Holden tries to attract their attention and favor with drinks, donations, or hot chocolate. Holden simply wants them to stay with him. As Holden continues to initiate conversations with people, no patterns emerge in terms of the type of person Holden approaches. He remains open to all who listen to him. Finally, Holden takes risks with some of the women he engages. Sixteen-year-old Holden flirts with a former schoolmate’s mother, hires a sex worker, and makes drunken advances towards a woman at her workplace. Holden’s extreme loneliness leads him to seek out people he does not like, people he does not know, and women with whom he should not flirt. In his desperation, Holden turns mostly to people who can not satisfy his need for human connection.

People he does not like

Holden feels so desperate for connection that he reaches out to people he does not like. Holden feels annoyed and even disgusted by Robert Ackley, a fellow Pencey Prep student. However, Holden confesses: “[Ackley] was sort of a nasty guy. I wasn’t too crazy about [Ackley], to tell you the truth…I asked Mal if he minded if Ackley came along with us. The reason I asked was because Ackley never did anything on Saturday night…” (p. 10, 18). Holden describes Ackley as “nasty” and admits that he does not care for Ackley. Despite Holden’s negative opinion of Ackley, he chooses to invite Ackley along with him and another boy on their weekend outing. As Ackley sleeps in the room next to Holden’s, Holden sees Ackley’s own isolation and can empathize. When Holden leaves Pencey Prep for Manhattan, he telephones a girl he sometimes dates, Sally Hayes. Holden shares, “I wasn’t too crazy about [Sally], but I’d known her for years. I used to think she was quite intelligent, in my stupidity…Anyway, I gave her a buzz” (p. 55). Holden no longer likes Sally, and does not think she is very smart. Holden calls to invite her on a date anyway because he has a history of dating with her. He knows if he talks to Sally, he has a chance to get a date. Later, Holden telephones Carl Luce, a former schoolmate. Holden explains, “I gave old Carl Luce a buzz. He graduated from the Whooton School after I left. He was about three years older than I was, and I didn’t like him too much, but he was one of these very intellectual guys” (p. 69). Carl Luce is another person Holden believes may meet him. As with Ackley and Sally, Holden shares that he does not like Carl. Holden hopes he and Carl can at least have an interesting conversation. Holden explicitly says that he does not like Robert Ackley, Sally Hayes, or Carl Luce, however, he invites them all to spend time with him. In his desire for human interaction, Holden indiscriminately contacts the people he knows.

People he does not know

Holden also tries to make connections with new people he encounters in fleeting situations. When Holden gets off the train at Penn Station, he attempts to befriend the first person he interacts with: a taxi driver. Holden asks the taxi driver to take him to a hotel, and on the way, Holden asks the driver: “Would you care to stop on the way and join me for a cocktail? On me. I’m loaded” (p. 31). Although he never seems to learn his driver’s name, Holden politely invites the man to spend time with him. Holden asks the man to stop work to go to a bar with him. Holden says, “somewhere,” as if he remains flexible and open to suggestions, and makes clear to the driver that he intends to pay for the driver’s drinks. Holden assures the taxi driver that he has enough money for the two of them. The next day at breakfast, Holden seeks interaction with more strangers. Two nuns sit down beside him at a breakfast counter and “They didn’t seem to know what the hell to do with their suitcases, so I gave them a hand…They let me give them ten bucks as a contribution…I swung the conversation around to general topics and asked them where they were going” (p. 56-57). Holden immediately helps the nuns with their belongings and offers them a monetary donation. Although only a teenager, without a job of his own, Holden insists that the nuns take cash from him. He proceeds to tell the nuns about himself, and also asks them questions. While he isn’t Catholic, Holden takes a great interest in the two nuns. After breakfast, Holden goes on a walk and encounters a child in the park. He asks the child if she knows his sister, and helps the child with her skates. He muses, “She was a very nice, polite little kid. God, I love it when a kid’s nice and polite when you tighten their skate for them or something. Most kids are. They really are. I asked her if she’d care to have a hot chocolate or something with me, but she said no, thank you.” (p. 61). Sixteen-year-old Holden doesn’t mind if his companion is a little girl, he simply wants to spend time with someone. He appreciates the girl’s good manners and attempts to extend their interaction. Holden wants to talk to someone - anyone - so he reaches out to strangers, including adult men, Catholic nuns, and children.

People with whom he takes risks

Holden asks people he dislikes to spend time with him, he engages strangers he meets in Manhattan, and he initiates risky situations on several occasions, all in an effort for some company. Holden seems not to care if his words and actions are illegal, inappropriate, or dangerous. When he leaves his school, teenage Holden meets Mrs. Morrow, a woman he learns is the mother of a former schoolmate. Holden guesses the woman is in her forties. They strike up a normal conversation, but Holden presses for more. Holden says to the woman: “Would you care for a cocktail? We can go in the club car. All right?…C’mon, join me, why don’t you?” (p. 30). At sixteen, Holden cannot legally buy alcohol for himself. Not only does he seem willing to break the law in front of Mrs. Morrow, he invites her to join him. In Holden’s desire to connect with someone, he extends a flirtatious invitation to the much older, married mother of a boy he knows. When Holden returns to his Manhattan hotel that night, he meets a man named Maurice who offers to send a sex worker to Holden’s hotel room. Holden agrees to Maurice’s offer but immediately laments: “That’s the whole trouble. When you’re feeling depressed, you can’t even think…I was already sort of sorry I’d let the thing start rolling, but it was too late now” (p. 48). Although he is a high school student on his own, Hoden takes a risk and allows a strange man, late at night, to send a woman to his room for sex. He regrets his decision to accept Maurice’s offer, but does not change the decision. The next night, at the Wicker Bar, Holden becomes very drunk, and directs his attention at a female employee. He remembers: “She kept telling me to go home and go to bed. I sort of tried to make a date with her for when she got through working, but she wouldn’t” (p. 77). Holden’s drunkenness, at a city bar by himself late at night, puts him in a vulnerable and dangerous position. Furthermore, the woman he asks to meet him later tells him multiple times to go home.

When Holden leaves his boarding school, he does not want to return home to his family immediately. He wants to put off what he knows will be an unpleasant reaction from his parents. The time between Holden’s expulsion from boarding school and his return home to his family casts him into a lonely space. He seeks human connection anywhere he can, and the desperation leads him to numerous unsatisfactory and even dangerous encounters. The people that Holden knows around him, the strangers in Manhattan, and the women towards which he makes unwise advances, do not make him happy. During or after most of his time with Ackley, Sally, and Carl, or his taxi cab drivers, the nuns, and the child, or with Mrs. Morrow, the sex worker, and the employee at the Wicker Bar, Holden feels dejected or depressed. These people do not ease his suffering. Holden’s final moments at Pencey Prep, and his return to Manhattan illustrates the vulnerability of a young person, especially during a challenging time. During his last moments at Pencey Prep, and his first days back in Manhattan, the only times Holden feels happy is when he thinks of his little sister, Phoebe, or spends time with her. Holden feels happy when he buys Phoebe a new record (p. 60), and as he watches her ride a carousel (p. 108). After many bad interactions, Holden can survive on the good times with his sister.

References

Salinger, J.D. (1951). The catcher in the rye. Little, Brown and Company.