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How far can I travel in time to be able to still understand the English we speak now, to the English they spoke in England?
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silverappleyard
While you wait for an answer, you might be interested in this related question:
When I hear Chaucer spoken in Middle English, it almost sounds more like Dutch than English. But though Shakespeare is closer in time to Chaucer than the present, his English is much easier to understand. What happened to English in between, and why?
with an excellent answer from /u/bloodswan