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How far back in time can you understand English?
(www.deadlanguagesociety.com)
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I've been a Rob Words channel fiend lately, about the same as you OP. I suspect if I was teleported back in time earlier than 1400 that I could learn quicker than someone who has never learned any form of English to a point, but it'd still be quite the effort. Then again I'm only considering listening and reading. I think learning to speak well enough to be understood in return is probably harder still, possibly worse than blank slate?