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Phoebe serves as Holden's confidante in the book. She is the one person who listens to him vent and the person he feels truly understands (or at least accepts) him. Whenever Holden is most upset or needs someone to talk to, he talks to his sister. So at the point he chooses to "chew the fat" with her, he is particularly upset or bothered by some aspect of his life, and by talking to Phoebe, he can reveal his feelings to someone who does not judge him.
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