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Holden is early for his date with Sally, so he waits for her and indulges in a bit of girl watching. Sally arrives ten minutes late, but since she is looking extremely nice, Holden decides not to be upset with her. They watch the play for which Holden has bought tickets, and he reluctantly admits the show is not bad. Afterward, Sally suggests they go ice skating at Radio City, mostly because she wants to rent one of those little skating skirts to show off her legs. However, both Holden and she are miserable skaters, and they finally retreat to the bar for cokes. While having refreshments, Holden is suddenly roused from his depression with the thought of running away. He asks Sally to go with him, but she dismisses his idea, thinking he is being weird. They fight and Sally leaves with hurt feelings.
This chapter shows Holden in an extremely agitated frame of mind; he insists he is "crazy" and repeatedly says, "I am a madman". Although Holden is able to state this, he is unable to see what prompts his strange behavior. He cannot understand that his need for companionship has driven him to near desperation.
As they have cokes, Holden suddenly decides he wants to run and away and invites Sally to go with him. He feels animated and excited at the prospect of the two of them together. Sally, however, does not even realize Holden’s seriousness when he proposes his plan. She responds with a typically safe, practical, middle-class approach, suggesting that they can do all of what Holden wants, but in the correct order and after they have finished with college. Holden is devastated to hear her practical response. In his near hysterical state of mind, he calls Sally a "pain in the ass". Quite naturally Sally is hurt, and the afternoon is ruined.
The real tragedy of this scene is that for a moment Holden thinks he has found the answer to his problem, thinks he has made a human connection, and feels there is hope. Unfortunately, as much as he tries to convince himself that Sally understands him and as much as he tries to think she should go with him, she is as far away from his emotional state as she can be. She does not understand Holden, which frustrates him even more. He feels he is so close to the solution, and in his frustration at discovering he is not, he strikes out and hurts the one person in the story who cares about Holden.