How far back in time could an English speaking person go, and still be understood. | AskHistorians Archive Observer

How far back in time could an English speaking person go, and still be understood.

by climbingoat

I guess what i'm asking would there be a point that old english speakers wouldn't be able to understand modern english?

Searocksandtrees

Hi, check out this thread, which has several examples across different time periods, and links to a handful of other posts

I am a native English speaker with a hypothetical time machine. How far back in time in England can I go and still communicate intelligibly with the locals?

and this one, where /u/bloodswan takes a deep dive into the Great Vowel Shift

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?