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In chapter 22, Holden becomes "even more depressed" while talking to Phoebe.
"Why the hell do you have to say that?" Holden asks, subsequent to Phoebe saying, "You don't like anything that's happening!"
Holden most likely reacts this way because
Phoebe's comment reveals that not even she ”the person who is closest to him” understands Holden.
Phoebe's remark to Holden is both offensive and innacurate; her comment depresses Holden because it indicates that Phoebe can be spiteful.
Holden knows that Phoebe's assessment of him is correct and he does not want to confront his problems nor reevaluate his view of the world.
Phoebe's remark was made in a snobby and affected tone, which Holden has not heard her use before; what she says depresses Holden because her actual demeanor clashes with his innocent image of her.
Phoebe's comment, and the way she says it, sounds to Holden like something that Allie would say; this depresses Holden because it reminds him yet again that Allie is dead.