Is it because he knows he needs to move forward from childhood to adulthood? Does he realize that he needs to get help or is it because he is just an emotional wreck and can't handle seeing his sister so happy while he is so miserable?
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In my interpretation of the novel, Holden is crying at this point not because he realizes that he needs to move from childhood into adulthood (this realization came to him when his brother died), but because he realizes that soon his little sister Phoebe will have to move from her childhood into adulthood. Holden values the sense of innocence that his sister represents, and as he watches her ride the carousel, he sees that already she is willing to take risks. He knows that soon enough, Phoebe will be ready to enter into adulthood and he fears that she will be corrupted by all the elements of the adult world that he despises. But Holden knows that he cannot prevent this from happening and that growing up is inevitable. So he cries as a symbol of the fact that life continues despite anything that he can do to prevent it from happening.
I think that he's happy.
I think that Holden is actually feeling, for once in the book, as if he is in a place where no one is being "phony." He is watching someone that he cares about (and there are few enough of those people) having pure fun. There is no reason at this point for him to be his usual cynical self. For this reason, he is actually happy for once and might be able to move towards being more of a regular person. I think that is why he feels the way he does at the end of Ch. 25.
I agree with #3 more than #2. This is the one moment where he feels that he and his sister are sharing a real, unartificial and genuine moment. He is genuinely overwhelmed by the joy and pleasure that he has with his sister at this moment, and, having spent the whole novel protesting about phonies doing phony things and having engaged in a number of phony activities himself, he can be real and just enjoy the moment.
It's about the loss of innocence. Holden recognizes that he lost his ability to simply and innocently enjoy those simple moments in life. He is sharing an innocent moment with Pheobe who remains clueless to the harsh reality of life, and even in that moment Holden's understanding of the harsh realities mars that moment for him.
I believe that Holden is crying while watching Phoebe is riding the carousal because he wishes he could regain his innocence. Holden is "advanced" for his young age. He drinks, smokes, and thinks about sex a lot. It is at this point in the story where he seems to understand the importance of being a child. His refusal to grow-up (think the lost foils and getting kicked out of school) shows that he is aware of wanting to stay a child, but his behaviors contradict this. This moment in the novel is perhaps the most profound look at Holden's true inner self. Unfortunately, for Holden, this moment comes too late.
I do agree with #2 as well as with #3. I can sense, as a reader, that Holden is in a safe place when he is with Phoebe. Therefore he can feel free from every limiting characteristic that he has bestowed upon just about everyone except for her. However, I do strongly believe that he feels anxious that Phoebe is, at some point, going to move away from her innocence and become an adult. Imagine what that does to someone like Holden, who feels that adults are the "enemy". I do feel that his tears are a result of both joy and sadness: He is happy to experience Phoebe's innocence, but he is also sad that, one day, it will go away.
I agree with a great deal written here. I think that Holden is happy being with his sister. Her company is the one place in his world where he will be loved unconditionally. Phoebe isn't a fake as he sees so many others. He may, also, be worried about her loss of innocence, but I don't know for certain that this moment can't reflect a loss of innocence for Holden as well. In truth, with his brother's death, Holden may have been confronted by a loss of innocence, but based on his behavior, I wonder if he has yet to embraced it totally—he may be fighting it. For there is no turning back when one turns that corner. In fact, I would argue that Holden's ultimate breakdown may indicate that he has not turned the corner…refuses to. Holden is struggling to find his place in the world, and there are so many people that disappoint him. He could also be crying because he is disappointed to himself…but once again, Phoebe's acceptance of him despite his "disappointing behaviors" may simply be too great a joy to endure without tears.
Holden really struggles in this book with the idea that adults are phony and live shallow lives. He does not want to become an adult, because he sees being an adult as losing not only one's innocence, but one's integrity. The carousel has been a symbol both of change and childhood for some time, so I think it's a perfect example.
I think that Holden is at peace at ths moment where time is not moving forward. Phoebe is on a carousel, symbolising childish pleasures but also a cyclical process. Phoebe is not going anywhere, unlike Allie who has left him and his trusted teacher who betrayed him. Here, at the carousel, time is static and Phoebe is supported by the carousel of childhood, watched over by Holden.
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