How far back in time could a modern day English speaker go and still be able to have somewhat of a conversation with someone?

by YellowMaverick
WhitechapelPrime

As a follow up question: I know the high level differences between old, middle, and modern English, but how close in pronunciation would words that made it through to today be? Would the written word be more effective in communicating, or the spoken word?

Searocksandtrees

Hi, this is one of the most popular questions in this sub. Here's a thread from the FAQ that has some good examples, but a search will turn up many more if you're curious