What's the furthest back in history that a modern English speaker could understand and communicate verbally with one from that time?

by boneyarsebogman

I was just thinking about this.. Obviously removing modern slang and words, how far back could I go back in time and be able to be understood and engage with an English speaker then?

I specify verbally, because I know written language has changed quite a lot throughout history.

Mictlantecuhtli

There's always room for discussion, but perhaps the section How far back could I go and still communicate? in our FAQ will answer your inquiry.