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

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In this video:

Contrary to what many a Grammar Nazi the world over would have you believe, language is constantly evolving, occasionally extremely rapidly, and there is nothing wrong with that, despite such individuals lamenting that fact pretty much as long as we have documented reference of people discussing language.

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Sources:

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https://www.quora.com/If-we-could-go-...
http://www.bbc.co.uk/history/historic...
   • What Shakespeare's English Sounded Li...  
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