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One of the things that is important about Winston's interaction with the old man, and with the proles in general, is that he feels they are the source of any possible change. That they must be mobilized and without them there is no hope of change as the party members are already too weak, too often spied upon, etc. His conversation with the old man demonstrates this somewhat irrational belief and the energy with which he pursues it, the same energy that will eventually lead to his arrest because he gets carried away.
He continues to try and push the old man to speak about things prior to the war, things about the party or about how people acted prior to the way things are now. He finds eventually that the old man's memory "was nothing but a rubbish heap of details," and the hopelessness returns, but he is quick to erase it by purchasing the antique piece of glass.
It is this search for hope for reason and meaning that eventually leads to his arrest.
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