1984

What is meant by “Tragedy belonged to a different time” why does Winston want to hold on to tragic memories?

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Tragedy was a part of the old pre-revolution world. It was a time when love and loyalty was not solely directed towards Big Brother. It was a time when people were free to feel emotion-life meant something more than mindless devotion to the party. This is why Winston tries to remember even painful memories because at least he can still feel something.