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Obviously Red knows that Ressler is a great guy and from 3x01 it seems that he has realized that Ressler cares a great deal for Liz.
But for some reason I can't see him hopping on board with the idea of them together in the future. I don't know why.
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There is nothing that can take the pain away. But eventually, you will find a way to live with it. There will be nightmares. And everyday when you wake up, it will be the first thing you think about. Until one day, it’s the second. ~ Raymond “Red" Reddington, The Blacklist
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