Were I a reasonably educated speaker of modern English planning a trip back in time to medieval England, how far back could I go and still understand others and make myself be understood without too much trouble?

by ynotsneezeroseselavy

idjet

Listen to this: https://www.youtube.com/watch?v=QE0MtENfOMU

Can you understand it? That's Chaucer in the late middle ages, Middle English. If not, no middle ages time travel for you. You won't get any earlier than Shakespeare, and you might struggle with that.