Middle English is the language which Chaucer spoke, and in which he wrote.

Middle English throve from the twelfth century to the fifteenth century, and represents the gradual amalgamation of Old English with Norman French following the Norman Invasion in 1066. During that time, several characteristic Old English letters drifted out of the alphabet:
thorn þ, Þ "th" sound (unvoiced)
eth ð Ð different "th" sound :) (voiced)
ash æ Æ; good question

There's also something called wynn, which looks a lot like thorn and seems to languish unrepresented in ISO 8859-1Latin-1. wynn signified some kind of "w" sound.

Middle English differed in vocabulary and sentence structure from Modern English. for example, they'd do subject-object-verb as in "I hym folwed", or verb-object-subject as in "taughte me my dame". Both examples are from Chaucer. Much of the vocabulary is recognizable, but "distorted"; of course, it's our own late modern English words which are "distorted" descendants of those words, not the reverse. Either way, you can recognize "folwed" as "followed" if you've got your wits about you.

The term "Old English" is horrifically misused. The language of Shakespeare and of the King James Version of the Bible -- the two were contemporaneous -- is early Modern English. Neither Shakespeare nor Chaucer ever wrote in Old English. The odds are about 10,000 to 1 (if not steeper) that what you call "Old English" is early Modern English.
As stated above, there were several letters in Middle and Old English which no longer appear in Modern English, but which are still interesting none the less, and still come up once in a while, particularly for medievalists.
  • Æ æ: "ash" pronounced like "a" in hat
  • Þ þ: "thorn" pronounced like "th" in thread; it is derived from the Germanic Runes or "Futhark." Interestingly enough, the form of this letter gave us that quaint word "ye" as in "Ye Olde Shoppe"--The loop of the Þ gradually seperated from the top end, forming what looked like a y, and thus leading to the written form "ye"--however, both forms--"ye" and "the" were used, until "the" eventually became the standard as education became uniformed in the late nineteenth century.
  • Ð ð: "Þæt" in English, but currently known by its Icelandic name "eth"; it is pronounced like "th" in leather
  • P p: "wynn" meaning "joy"; pronounced like "w"; this letter is not supported by HTML, and so I have given an aproximation found in the shape of the letter P, which looks almost identical. It is also derived from the Runes/Futhark, and is generally rendered "w" in most texts.
  • 3 3: "yogh" whose pronounciation is complicated, but is usually rendered "g" or "y"; it is not represented by HTML, but looks like the number 3, which I have substituted here.

BrianShader says "re Middle English : If I remember rightly, the original form of the "thorn" letter remained alongside the 'y' form until the printing press came over from Germany. These presses had no thorn symbol and so y was used instead, and thus the original form was completely erased."

Me says Interesting point.

To which Txikwa offers this rebuttle: "re Middle English: There were manuscripts in the 1300s where Y was used for thorn, i.e. where they'd become identical in shape, so it wasn't just a matter of printing."

Me says Ahh. Getting more interesting.

OE = Old English, ME = Middle English (c. 1150-1450), MnE = Modern English.

Grammar

The main grammatical difference between OE and ME was the loss of most inflections. Old English was a heavily inflected language like German. The reduction and loss of these inflections began before 1066, notably in the Danelaw where it was in contact with speakers of the closely related Old Norse, but it accelerated after the Conquest.

The OE dative plural -um changed to -en, becoming identical with an existing ending and also with endings -an and -on. Endings -e, -a, and -u also merged. These unstressed vowels lost their distinctive sounds and became the schwa or neutral vowel, as in MnE bitten, button. Eventually all these endings, now written -e, became silent, and the final -e served only to mark the length difference between e.g. rat and rate. The silent -e lingered in spelling for many centuries more.

Where OE had a multiplicity of plural formations, ME generalized the -s, -es ending, keeping a lesser number with -en (of which several remain, like oxen).

In OE, past participles had the prefix ge- as in German (er ist gekommen 'he has come'). In ME this become i- (also written y-), and eventually disappeared. Its legacy is the odd archaism like yclept, and the song Sumer is icumen in, which means 'Summer has come in' (cf. German), not 'is coming in'.

OE had a distinct present participle in -and (German -end) as in 'a laughing hyena', and gerund in -ing (German -ung), as in 'laughing is infectious'. In ME the gerund was generalized and the participle dropped out.

Literature

The principal monument of ME literature is of course The Canterbury Tales. Because Chaucer was a Londoner, his dialect is the ancestor of the kind of English most of us now speak, so is rather easier to understand than the contemporary poem Sir Gawain and the Green Knight, from the North-West Midlands. This is a pity, since Gawain is a beautiful poem, well worth struggling through. Other important literature of the period includes Piers Plowman, Pearl, Patience, Ancrene Riwle (rules for anchoresses), Ayenbite of Inwit (remorse of conscience), Sir Orfeo, and the historical-cum-legendary Brut of Layamon, which includes a version of the King Arthur story.

There is a long didactic poem Ormulum by a monk called Orm. It is stupefyingly boring as literature, but fascinating as language because Orm tried to institute a spelling reform in which a short vowel was indicated by doubling the following consonant. This provides a very valuable guide to the pronunciation of ME. It's sad that it's virtually never credited as the Orrmulum of Orrm, as he wanted.

Dialects

OE had four principal dialects, Northumbrian, Mercian, West Saxon, and Kentish. The standard literary language in the later period was West Saxon, that of the court of King Alfred at Winchester in Wessex. Because of the Danish occupation of the east, Mercian was dividing into two, West Midland and East Midland. From 1066 the centre of culture was London, midway between the Kentish and East Midland areas. As the new universities of Oxford and Cambridge were also in the East Midlands, it is this dialect that became the basis of standard modern English.

The northern dialect remained uniform until about 1300, then over the next hundred years rapidly diverged into three, those of Yorkshire, Northumberland, and lowland Scotland. Yorkshire was influenced by the south, and took on an intermediate character. As Scotland was an independent kingdom, the Scots or Lallans dialect was increasingly perceived as a separate language. This identity diminished after the union with England in 1603. Characteristic features include plural -is, a strong fricative spelt quh for southern wh, and the fact that long a didn't change to o as it did in the south (hame, camb).

Both the southern dialects used voiced versions of f, s initially: vriend, zummer. Kentish later lost this but it may still be heard provincially in the South-West. The modern word vixen comes from a southern feminine of fox.

Vocabulary

From about 1250 the trickle of borrowings from French turned into a flood, turning English into the hybrid it is today.

It must be borne in mind that French has also changed a great deal since then, and the pronunciation of borrowed words would have been quite different from modern French. The ending -ation would have been more like -AH-see-ohn.

Pronunciation

ME spelling is confused, to say the least. The change of sounds from OE, in the different dialects, and with overlay of French habits, produced a complex system that was stabilized but not standardized when printing came in at the end of the ME period. But because OE spelling was more accurately phonetic, we can untangle many of the details of the sound changes of ME.

The guttural written with yogh, later gh, often disappeared in the southern dialects, leaving a long vowel, as in light, though. In other circumstances it became y as in day, w as in law, or f as in rough.

The clusters ld, nd, mb caused short vowels to lengthen: wild, blind, climb.

Middle English comes to an end as the Great Vowel Shift wreaks major changes on its pronunciation. Before this you could pronounce it roughly like any other European language. After it comes the Early Modern English of the Elizabethan/Jacobean playwrights and the Authorized Version.

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