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In a way, I think you're right. These characters do have trouble communicating their feelings. I think it has to do with perspective. The big guy in "Only the Dead Know Brooklyn" has trouble communicating the metaphor of 'drowning' in the vastness of the city to the more specific literal-minded narrator. The big guy is on some wandering quest to get to know Brooklyn and the narrator can't figure this out from what the guy says to him. The big guy is figurative and vague, almost wistful (and drunk). The narrator is no-nonsense, literal and genuinely sympathetic but more practical, less philosophical.
In "The Far and the Near," it is not so much an individual or cultural difference as it is in the previous story. It's more about perspective and a kind of self-centrism. In his mind, the engineer had created this ideal relationship, as if he knew the woman and her daughter intimately. He fumbles with his explanation because upon meeting them, he finds that they (like himself) have become old and haggard. His idyllic conception of them is shattered because the image he had of them (from afar) was idealistic and unchanging. When he sees that they have changed, he's unable to communicate because he's so bewildered and confused that this one image of faith and hope is gone. It's as if he'd put them on an immortal pedestal, like they were angels watching over him. Once he finds them mortal, he confronts his own mortality. "suddenly he knew he was an old man." The fact that this is the moment when he faces his own mortality compounds his confusion (loss of faith in the 'unchanging' wavers) - and adds to his inability to communicate his feelings.
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