yes or no
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No, Winston could not answer that question. From the text:
Winston sat for a minute or two gazing at his empty glass, and hardly noticed when his feet carried him out into the street again. Within twenty years at the most, he reﬂected, the huge and simple question, ’Was life better before the Revolution than it is now?’ would have ceased once and for all to be answerable. But in effect it was unanswerable even now, since the few scattered survivors from the ancient world were incapable of comparing one age with another.