Basic Information
Languages are not stable, and English is no exception. If you go back in time even just a few hundred years, you'll find slang and phrasing quite puzzling, and be amazed at how different (and inconsistent) the spelling is.
Old English has strong Germanic roots, and is almost entirely indecipherable to a Modern English Speaker that hasn't studied it extensively. It was spoken from the 5th Century until sometime around the end of the 11th Century. If there's one familiar word per sentence, consider yourself lucky.
Middle English has French/Norman influences, and uses plenty of words that have since been retired. With time and effort and a reference book, most modern readers will be able to decipher the majority of it, though it feels pretty alien at first glance. Spelling is particularly strange, especially in regards to vowels.
Early Modern English, which is the language of Shakespeare, came to be in the wake of the Great Vowel Shift. The Renaissance, the Printing Press, and further exposure to other languages caused a shortening of English vowels. The result was Early Modern English, which is poorly recreated by the faux-language of the trope called Ye Olde Butcherede Englishe.
What you'll recognize as real Modern English didn't come about until after Samuel Johnson published the first major English Dictionary in 1755. Prior to that setting of the standard, spelling was very piecemeal and inconsistent.
See Also: Language and Language Tropes
Sources
Game and Story Use
- A Time Traveler is likely to have a hard time with the language. Some GMs will hand wave this will a little Ye Olde Butcherede Englishe for the sake of plot, but other GMs prefer realism and the challenges it provides. Do not go blindly into that Portal To The Past, or you might be in for a rude awakening. In particular, prior to 1000 AD, expect your English won't get you anywhere unless the game is a comedy.
- The Continuum RPG has some specific metagame tricks for handling in-character translation, as they expect you to be fairly accurate with language (or rather, they have language change realistically, but give the party the tools to get by with a little effort).
- If there's no time travel, it's probably easiest to substitute modern language and vernacular for the default tongue of the setting. Don't worry about the "Thou Didst Give Me Thy Counterfeit Fairly These Monthes And Fortnights Past, Oh Where Hast Thou Been?" and the like, unless you're trying to depict a specific character who's very formal (or not very fluent). That said, some modern phrases might take it too far: "Wazzup biotch?" may strain verisimilitude beyond belief, especially from the lips of a Knight or Courtier.

