Why will they both be lonely if they are walking together?

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Well, they aren't really walking together. Perhaps they appear to be, in the imagery and the vision of the poem, but they aren't really. Walt Whitman, Ginsberg's great idol, died long before he was born. Garcia Lorca, too, died when Ginsberg was only ten years old. Writing them into the...

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Well, they aren't really walking together. Perhaps they appear to be, in the imagery and the vision of the poem, but they aren't really. Walt Whitman, Ginsberg's great idol, died long before he was born. Garcia Lorca, too, died when Ginsberg was only ten years old. Writing them into the supermarket tears them away from their own eras to keep Ginsberg company, but the poet knows it's not real. He is quite aware that he's separated from his literary idols by lengths that can never be crossed. When Ginsberg says he feels lonely when walking with them, he means that it pains him that he will never do that in reality. He attributes the same feeling to Whitman, who he imagines also sometimes felt lost and alone without someone to share his point of view.

It can be quite safely assumed that Ginsberg, a great poetic mind, feels lonely in a general sense. He longs for companionship that only similar souls can bring but feels like the people who could have provided him with that are gone. "A Supermarket in California" is a wishful dream, then, Ginsberg's fantasy of how much he'd like to run into his idols at a random supermarket, even if it would be just to reflect on the problems of America's society together. That, however, is not just improbable, but impossible for him. It's understandable why that makes him feel quite lonely.

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