Still feeling restless, Holden changes his shirt and goes downstairs to the Lavender Room, the Edmont’s nightclub. Before he leaves his room, he thinks again about calling his little sister, Phoebe. Referring to her as “old Phoebe,” he gives a description of her character that is remarkably similar to the description he gave of Allie in Chapter . Like Allie, she has red hair and is unusually intelligent for her age. He recalls the time he and Phoebe went to see Hitchcock’s The Steps (despite his professed loathing for the cinema, he has clearly seen many movies and has strong opinions about them). He notes Phoebe’s humor and cleverness, and mentions that she writes never-ending fictional stories that feature a character named “Hazle” Weatherfield. According to Holden, Phoebe’s one flaw is that she is perhaps too emotional.

In the Lavender Room, Holden takes a table and tries to order a cocktail. He explains that due to his height and his gray hair, he is often able to order alcohol, but, in this case, the waiter refuses. He flirts and dances with three women who are visiting from Seattle. They seem amused but uninterested in this obviously young man who tries to appear older and debonair. After tolerating him for a while, they begin to laugh at him; they also depress him by being obsessed with movie stars. When Holden lies to one of them about having just seen Gary Cooper, she tells the other two that she caught a glimpse of Gary Cooper as well. Holden pays for their drinks, then leaves the Lavender Room.

As he walks out to the lobby, Holden reminisces about Jane. Their families’ summer homes in Maine were next door to one another, and he met her after his mother confronted her mother about a Doberman pinscher that frequently relieved itself on the Caulfields’ lawn. Holden and Jane became close—Jane was the only person to whom Holden ever showed Allie’s baseball glove. One day, Jane’s alcoholic stepfather came out to the porch where Holden and Jane were playing checkers and asked Jane for cigarettes; Jane refused to answer him, and, when he left, she began to cry. Holden held her, kissing her face and comforting her. Apart from that incident, their physical relationship was mild, but they used to hold hands constantly. When you held Jane’s hand, Holden reminisces, “all you knew was, you were happy. You really were.” Holden then feels suddenly upset, and he returns to his room. He notices that the lights in the “perverts’” rooms are out. He is still wide awake, so he heads downstairs and grabs a taxi.

Holden takes a cab to a Greenwich Village nightclub called Ernie’s, a spot he used to frequent with D. B. His cab driver is named Horwitz, and Holden takes a liking to him. But when Holden tries to ask him about the ducks in the Central Park lagoon, Horwitz unexpectedly becomes angry. At Ernie’s, Holden listens to Ernie play the piano but is unimpressed. He takes a table, drinks Scotch and soda, and listens to the conversations around him, which he finds depressing and phony. He encounters an obnoxious girl named Lillian Simmons, whom D. B. used to date, and is forced to leave the nightclub to get away from her.

By this point in the novel, it’s clear that loneliness is at the heart of Holden’s problems. When he arrives in New York, it is already quite late in the evening, but he embarks on an almost manic quest for interaction. His call to Faith Cavendish in Chapter hinted at Holden’s desperation—calling a girl you’ve never met in the middle of the night is not quite normal—but here we see the depth of Holden’s feelings of loneliness and alienation.

Despite his independent nature, Holden demonstrates how badly he needs companionship. In these chapters especially, his thoughts are always of other people. He thinks about Phoebe, he repeatedly remembers Jane, and he mentally ridicules the people at surrounding tables. But Holden never mentions himself. He avoids introspection and reflection on his own shortcomings and problems by focusing on the world around him, usually through a dismissive and critical lens. His focus on other people reveals the extent to which he longs for companionship, love, and compassionate interaction to help him through a difficult period in his life.

Through his nostalgic memories of Jane, we gain insight into the type of companionship Holden wants. He mentions that he knew he was happy when he was with Jane—this is a certitude that he is lacking at the present moment. His memories of Jane are especially touching because he describes a very deep emotional connection. Additionally, their moments of intimacy were subtle and extremely personal, free of any sort of posturing or phoniness.

The key moment of Jane and Holden’s relationship bears a curious resemblance to Holden’s present situation. After her stepfather’s intrusion, Jane is overwhelmed by a pain she cannot articulate, a deep sadness that she cannot put into words. Holden, full of silent compassion and understanding, knows what to do to help her through trouble. Now, he finds himself in a similar situation, struggling with a pain that he can’t talk about with anyone in the book, including the reader. He desperately needs the same deep, compassionate connection he says he once experienced with Jane.

Holden’s self-delusion and unreliability as a narrator continue to grow. When he enters the Lavender Room, he depicts himself as a wise-beyond-his-years, debonair playboy. But because the waiter refuses to serve him alcohol, and because the girls laugh at his advances, we doubt that Holden’s self-description is accurate. Holden rationalizes the girls’ dismissal of him by saying that they are silly tourist hicks. Although there does seem to be a bit of provincialism in their character, it’s fairly clear that the girls are amused by the situation and that they indulge Holden in his flirtation out of pity combined with a touch of mockery. Holden likes to imagine that he is a mature individual who perceptively sees all the hidden details around him, but in actuality he’s just a kid. Once again, Holden’s inability to understand the world around him—or, perhaps, his unwillingness to acknowledge the world around him—reveals his profound disconnection and isolation.