How Far Back in Time Could an English Speaker Go and Still Communicate Effectively?

Fascinating video, Meanderer. It brought back a memory of my high school English teacher, a colorful "spinster" type, as they were called in those days. She was a great teacher, and most of the time we were scared to death of her.

She loved Chaucer, and one day she read that description of the gentlemanly knight, in old English, accent and all. Then she looked off into the distance with a dreamy expression, and said plaintively, "And where is he now?"
 
Remember the song "Why Can't the English?" in My Fair Lady?

"The Scotch and the Irish leave you close to tears.
There even are places where English completely
Disappears. In America, they haven't used it for years!"
 
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