Holden Caufield is in his hotel room at The Edmont as Chapter ten begins. He is getting ready to go to the Lavender Room, which is a nightclub downstairs in the hotel. He has been thinking about calling his little sister, Phoebe. Holden tells us all about Phoebe, who is ten years old. He loves his sister. He also believes all his siblings are smart. D.B. is a talented writer, Allie, who has passed away, was a math whiz, and Phoebe has gotten all "A's" since first grade. Holden tells us, "As a matter of fact, I'm the only dumb one in the family."

Holden describes all the endearing characteristics of Phoebe. We see a side of Holden that is very different from the embittered, cynical misanthrope, disgusted with the phony ways of everybody. His little sister just enchants Holden, and she may even be his best friend. Phoebe has bright red hair that is similar to the color that Allie had. He tells us, "You'd like her. I mean if you tell old Phoebe something, she knows exactly what you are talking about." Holden can confide in Phoebe, and this fact lessens his sense of isolation. We see that she is a very important figure in his life. He misses her and would call her if he weren't so sure his parents would answer the phone and also because he knows that Phoebe is now sleeping because she is only ten years old.

When Holden goes downstairs to the Lavender Room, he strikes up a conversation with three women in their thirties. They are tourists, who all work for the same insurance company in Seattle, Washington. According to Holden, Laverne and Marty are ugly and Beatrice, the blonde, "wasn't too bad. She was sort of cute." The women find it extremely amusing that this seventeen-year-old boy is hitting on them. Holden notices that they keep giggling at him and tells us "I should have given them the Freeze after they did that, but the trouble was, I really felt like dancing."

Holden does end up dancing with all three women. Beatrice a great dancer. She was a "moron" according to Holden, but he fell "half in love" with her because she was such a good dancer. They are typical star-struck tourists and keep looking around to see if they can spot any famous people as if any famous people would go to The Lavender Room, muses Holden. The women suddenly tell Holden that they have to leave because they have to get up early to see the first show at Radio City Music Hall. They leave Holden with the bill. He feels it was kind of rude to stick him with the whole bill, which even included the drinks they had before he sat with them. Also, the fact that they were all doing such a touristy thing as going to Radio City Music Hall "makes me so depressed I can't stand it", Holden complains.

After the girls leave, Holden decides to leave as well. He says, "There isn't any nightclub in the world you can sit in for a long time unless you can at least buy some liquor and get drunk. Or unless you're with some girl that really knocks you out." Holden could not get served alcohol because he is under-aged, so he was just drinking cokes all night while the women were drinking Tom Collins drinks and Bourbons.

As Holden walks to the hotel lobby, he starts thinking about "old Jane Gallagher" again. He tells us how they used to play tennis and golf and how they were together almost every day in the summer. Jane is also the only person outside of his family that he ever showed Allie's cherished baseball glove with the poems written all over it in green ink. Holden goes into detail about how they almost got close to "necking", but it was in a very sad context. It involved the fact of Jane having to deal with her drunken stepfather, who was most likely molesting her. When Holden asks her directly if her stepfather was messing with her, Jane just begins to cry. Holden reacts by giving her little kisses all over her head and face but not on the lips. They would also hold hands when they would go to the movies. Holden said, "She was terrific to hold hands with." And, also, "You never even worried with Jane, whether your hand was sweaty or not. All you knew was you were really happy. You really were." It is easy to understand why Holden keeps getting upset that Stradlater went on a date with Jane. He is in love with her, but it is a love that is chaste. Holden puts Jane up on a pedestal and cannot think of her sexually because he thinks that it would be cruel, especially since he suspects she has suffered some type of sexual abuse from her stepfather.

Holden gets restless after all this thinking about Jane. "Especially," he says, "every time I got to the part about her out with Stradlater in that damn Ed Bank's car, it almost drove me crazy." So, he decides to go out to a bar that his brother, D.B. used to frequent, called, "Ernie's" in Greenwich Village.

Horwitz is the name of the cabbie who takes Holden to Ernie's. The cab driver is unable to answer Holden's question about where the ducks in Central Park go in the winter, but he does address the fate of the fish in the winter. Horwitz is quite an odd character. He gets very excited explaining to Holden about how the fish freeze in the water and get nutrition from the seaweed or algae and then when the ice thaws, the fish swim around again. Horowitz is very intense and his sudden bursts of anger alarm Holden. Nonetheless, Holden invites Horwitz to come and have a drink with him. Horwitz comments on Holden's young age and asks why he is not at home asleep and then, declines Holden's invitation.

We are once again privy to Holden's disgust with phony people as he moves around inside the very crowded bar. The customers are all phony. Their conversations are moronic. Even Ernie, who was an accomplished musician, is pandering to the crowd, and, like his brother, D.B. has "sold out" and is now an embarrassing phony.

As Holden finally gets served an alcoholic drink, one of D.B.'s old girlfriends, Lillian Simmons, calls out to Holden. She is with a Naval Officer and is just thrilled to see Holden. Lillian is also a big phony, according to Holden; she is a big phony, with big breasts. She invites Holden to come and sit with them at their table, but Holden knows she is just trying to impress him so that Holden mentions her to his brother, D.B. So, Holden says he has to leave, and he returns to the hotel telling us, "People are always ruining things for you."

In chapters ten through chapter twelve, we see Holden in action. He comes on to three middle-aged women. He invites another cabbie to have a drink with him and ventures out, by himself, to a bar in Greenwich Village. Holden has a lot of guts for his age to behave in such an extroverted manner with adults. We also see a far more tender, and sensitive side of Holden as he describes his feelings for the two most important girls in his life; his ten-year-old sister, Phoebe, and Jane Gallagher.