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What are similarities and differences between Holden Caulfield and Esther Greenwood?

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Holden Caulfield and Esther Greenwood are both discontented despite their privileged backgrounds. Holden is alienated at Pencey Prep, while Esther feels empty despite her academic success and job in New York. Both are obsessed with innocence—Esther with the Rosenbergs and Holden with Central Park ducks—due to personal losses. However, Holden is critical of others' phoniness, lacking self-reflection, whereas Esther is intensely self-critical and aware of her shortcomings.

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Holden Caulfield in The Catcher in the Rye and Esther Greenwood in The Bell Jar are both miserable in the midst of academic privilege and material wealth. Esther Greenwood says at the beginning of the novel:

"I knew something was wrong with me that summer, because all I could think about was the Rosenbergs and how stupid I'd been to buy all those uncomfortable, expensive clothes, hanging limp as fish in my closet, and how all the little successes I'd totted up so happily at college fizzled to nothing outside the slick marble and plate-glass fronts along Madison Avenue. I was supposed to be having the time of my life."

Though she has won a scholarship to college, where she has been very successful, and she is working at a magazine in New York, she is desperately unhappy. Nothing from the outside world brings her joy, and she feels empty and...

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miserable despite the fine clothes she has bought at Bloomingdale's.

Similarly, Holden begins his narrative talking about his misery while attending Pency Prep:

"Where I want to start telling is the day I left Pencey Prep. Pencey Prep is this school that's in Agerstown, Pennsylvania. You probably heard of it. You've probably seen the ads, anyway. They advertise in about a thousand magazines, always showing some hotshot guy on a horse jumping over a fence."

He, like Esther, is the beneficiary of a top-notch education that would make others envious, but he is miserable. He feels distanced and alienated, though he has, by outward appearances, every reason to be happy.

Like Esther, who is obsessed with the execution of the Rosenbergs (who were alleged spies), Holden has his obsessions. For example, he is obsessed with the ducks in Central Park. He says:

"I live in New York, and I was thinking about the lagoon in Central Park, down near Central Park South. I was wondering if it would be frozen over when I got home, and if it was, where did the ducks go. I was wondering where the ducks went when the lagoon got all icy and frozen over. I wondered if some guy came in a truck and took them away to a zoo or something. Or if they just flew away."

Esther is obsessed with the Rosenbergs, who she sees as innocent victims, and Holden's obsessions include the ducks in Central Park, who he sees as innocent and subject to removal or to freezing. Both Esther and Holden relate to innocent victims because they also are innocent but treated harshly by fate (Holden loses his brother to cancer, and Esther loses her father when she is nine).

Holden and Esther are different in that Holden sees others as phony and is critical of others without being critical of himself. For example, when Spencer describes Holden's parents as "grand," Holden thinks, "Grand. There's a word I really hate. It's a phony. I could puke every time I hear it." Holden sees everyone and everything around him as fake, but he doesn't ever note the falseness in himself. Unlike Holden, Esther is intensely self-critical. For example, she says, "I'm five feet ten in my stocking feet, and when I am with little men I stoop over a bit and slouch my hips, one up and one down, so I'll look shorter, and I feel gawky and morbid as somebody in a sideshow." She is self-reflective and finds herself constantly lacking, but Holden directs his animosity and criticism at others rather than at himself. 

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