The transition from Old English to Modern English was a process, not an event
Changes in language don’t occur overnight, though slang terms come in and out of use relatively quickly and new words are invented while others fall into disuse. The rules of grammar you learned in school are the same ones your parents were taught and what your own kids will (or do) use. A few new words are tossed in the mix every few years to keep things interesting (remember the uproar when “ain’t” was added to the dictionary?).
The transition from Old English to Middle English to Modern English was a process rather than an event — the rules didn’t all suddenly change on May 24, 1503. Before the Normans invaded England in 1066, the people living in Britain spoke Old English or Anglo-Saxon. Some of the words from that time are still with us — the ones of the vulgar four-letter variety. Old English was so unlike Modern English it’s fair to view it as a foreign language. For example, here are the opening lines of the poem Beowulf:
Hwæt! Wé Gárdena in géardagum
þéodcyninga þrym gefrúnon
hú ðá æþelingas ellen fremedon.
I’m completely lost. Something about a garden, maybe?
Modern English translation as follows:
Listen! We — of the Spear-Danes in the days of yore,
of those clan-kings — heard of their glory,
how those nobles performed courageous deeds.
Yeah, not even close.
Save a horse, ride a Chaucer.
Let’s bump it up a bit to Chaucer’s time at the turn of the 14th century, when Middle English was in use (circa 1100 through 1450). The Canterbury Tales kicks off with:
Whan that Aprill, with his shoures soote
The droghte of March hath perced to the roote
And bathed every veyne in swich licour,
Of which vertu engendred is the flour
No walk in the park, but not completely indecipherable like Anglo-Saxon Old English.
When April’s gentle rains have pierced the drought
Of March right to the root, and bathed each sprout
Through every vein with liquid of such power
It brings forth the engendering of the flower
The real problems would arise with speaking — all the letters that are silent today were pronounced back then, which would make effective communication challenging at best. A simple conversation would most likely be possible — with the aid of some pointing here and there — but any sort of intellectual discourse would be off the table.
I have never seen anyone so chill while stabbed through the dome piece.
What differentiates Middle English from Modern English is the Great Vowel Shift, which brought about a huge change in the pronunciation of the long vowels between Chaucer’s era and Shakespeare’s. For example, the word “sheep” in the 1300s would be pronounced as “shape,” more or less. We may think that’s a bit nuts, but read this sentence aloud: “I sat and read what he had to read,” or “A rough-coated, dough-faced ploughman strode through the streets of Scarborough, coughing and hiccoughing thoughtfully,” before passing judgment on our medieval forbearers for their nonsensical pronunciation practices.
“‘Tis but a scratch” — the Black Knight.
Reading Middle English would prove to be much easier than holding a conversation with a medieval peasant or even a duke. One single word could have several different pronunciations and meanings that could vary from village to village. Once the common folk became more educated and literate, word definitions became more uniform from place to place, but pronunciations, or accents, still varied widely.
We arrived at our current pronunciations of most words around 1500, which most agree is the dawn of the Modern English age. William Caxton, the first English printer, wrote the following in the late 1400s, and it’s not all that hard to puzzle out:
For we Englysshe men ben borne under the domynacyon of the mone, whiche is never stedfaste but ever waverynge, wexynge one season and waneth and dyscreaseth another season. And that comyn Englysshe that is spoken in one shyre varyeth from a-nother…
For we Englishmen are born under the domination of the moon, which is never steadfast but ever wavering, waxing one season and waning and decreasing another season. And that common English that is spoken in one shire varies from another…
Not such a stretch from where we are today, certainly when compared to Old English.
Legless Jesus says: “Is that a pitchfork in your pocket or are you just happy to see me?”
Communicating with Shakespeare would be relatively easy aside from the occasional head-scratching moment, but, for the most part, both parties would be able to get the gist just fine.
Post-Shakespeare, you’d probably have no trouble at all.
We may be able to understand Shakespeare, but could we understand his butcher or blacksmith? And how much of our understanding springs from his work being required coursework for most of us?
Post-Shakespeare, you’d probably have no trouble at all. The Bard did much to shape the English language and how people express themselves and invented many words and figures of speech in common use today.
So, we could probably go back to around 1500 or so and communicate with contemporary English speakers — and they with us. Of course, the level of success would be contingent on a number of factors, including the level of education of both parties, the dialects (some are easier to comprehend than others), and the subject matter (keep it to things familiar to all concerned, no PC vs. Macs or other topics bound to befuddle a Tudor-era Englishman).
So obviously, the closer you get to our own time, the easier mutual understanding would be. A conversation with Ben Franklin would flow better than one with Sir Thomas More, and let’s face it — be infinitely more entertaining. Unless of course, you’re into hair shirts and self-flagellation, and who am I to judge?