What’s the farthest I could travel back in time and converse properly in English?

And what caused this ‘new style’ of English speaking [that we know (and love) today]?

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    If you wanted to understand everything it would be a lot more recent than if you wanted to be able to get most of it. Also, it depends on the person. I couldn't make much of Chaucer in it's original in high school but my friends who got into Yale and Harvard seemed to be able to make sense of it. I get about 90% of the thrust related to morals and plot-line but maybe only 50% of the connotations to the wittier lines in Shakespeare. I think I grasp nearly the entirety of Ben Franklin's writings and most his humor even though words were used differently then, especially when used figuratively. – Tom22 Apr 11 '18 at 17:27
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    If you're interested, then you really need a whole book (or video series) on the subject. One example is "The Story of English" (book and video series) by Robert McNeil et al. en.wikipedia.org/wiki/The_Story_of_English – Green Grasso Holm Apr 11 '18 at 17:27
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    Even better, David Crystal's Cambridge Encyclopedia of the English Language. Or, if you really want to know how it works, Larry Trask's Historical Linguistics. As for your question, if you are a native speaker of an English dialect, then you could probly go at least 200 years back and still understand the lingo, almost anywhere it's currently spoken. If you go to the right places, maybe up to 500 years back. But if you go where the GVS hadn't happened yet, you're lost. – John Lawler Apr 11 '18 at 17:52
  • Probably not as far back as you think. There is a great difference between the spoken word and the written word, especially when you consider that you do not have to go very far back for many people to be illiterate and generally not well educated. Culturally, you would probably find topics of conversation very different, and the ways that people would talk of things. You may well understand the individual words, mostly, but still not get the sense of the conversation. – Lee Leon Apr 11 '18 at 18:30
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    0 years. Without traveling. Have you heard the kids these days? It sounds like English but what are they talking about? What with all their Pokémon and thotties and quantum blockchain molly. – Mitch Apr 13 '18 at 11:47

Were you to buy the Oxford annotated Shakespeare of Hamlet, you would find that it seems very ancient because of turns of phrases, idioms, and small grammar changes that are really not that large; once you know them it reads quite like a modern tale. The footnotes help a lot.

I lived in the UK for 3 years recently, after having worked for a British bank for over 10. It is amazing how hard it is to understand native UK speakers after being back in the U.S. for 2-3 weeks. Once back in the UK, you quickly align with local language, spelling, and usage when immersed - even in your native language.

I imagine 16th century English would be easy to adopt if you were a native English speaker.

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