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Abbreviate ED as earlier dialects of your modern first language(s). I desire to read writing written in only ED (eg: philosophy written in English or French dated from 1400) and NOT in languages which must be learned from scratch, but I have been failing to understand ED's olden morphology and syntax. Old vocabulary is not a problem because dictionaries address it.

1. Without a modern gloss or paraphrase for the work in ED, should you learn ED? If so, how? As if the ED were new languages? If not, how can you understand the original texts written in ED?

2. I can read and ask not about writing after 1850, because their grammars resemble today's grammar.

3. I ask not about ED that simply differ too much, and must be learned as a new language (eg: Old English).

4. This question presumes the inefficiency and futility of struggling word-by-word, which I already attempted to no avail. As I wrote on ELL, it is too inefficient to question anew every long sentence that confuses me, and so I must transcend this approach 'by chance', which feels like a wastefully haphazard, torturous crawl of piecemeal creeps that hobble too narrowly to reach, even the rungs towards, the apex of sentential comprehension sought.

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    Despite your #4, the answer is indeed practice. As it is with the great majority of your questions. – Dan Bron Sep 16 '15 at 14:55
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    You refine your guesses as you progress further through the text. If a later passage contradicts what you took an earlier passage to mean, then you alter your hypothesis until everything you've read up to that point is consistent with it. In other words: you simply read. It is not possible to have factual confirmation of every idea every author has tried to express in every passage of every text ever written (and if such a confirmation existed, it, itself, would be a written work. And now you've got two problems.) – Dan Bron Sep 16 '15 at 15:10
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    Without a modern gloss on English from 1400, you should be lost, even if you are a native speaker of English. The way you start is with three books: a dictionary, a grammar (with lots of examples), and a chrestomathy, which is a selection of various readings in the olden language, with translations and notes. What you do is go through the chrestomathy from easy to hard and do it word-by-word, not asking Why something happens, but rather noting What actually happens, and learning that it does happen. This is the experience you'll need. – jlawler Sep 16 '15 at 19:09
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    And you'd better become very familiar with the philosophies discussed, and their peculiarities and idioms, as well; knowing a language doesn't make anybody capable of understanding philosophic writing. Especially since the philosophers in 1400 were undoubtedly writing in Latin, and not in English or French. – jlawler Sep 16 '15 at 19:10
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    +1 that (philosophy). What makes Aristotle hard to read -- in English -- is not the language, but the content, and especially the context. – user6726 Sep 16 '15 at 19:28
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One approach that linguists use is to train themselves in reverse chronological order. I'd suggest you do the same:

Read a few hundred pages in each century, going backwards. Choose similar genres and topics if possible. This allows you to adjust to changes in vocabulary, grammar or simply fashion in phrasing.

Three things you may want to look out for:

#1 You may go back to the 1800's for your first read, but from there on, do not move on until you feel at ease reading.

#2 Plan out your journey beforehand. Make sure you know the final piece you want to arrive at, and choose the intermediate steps so they lead into it.

#3 Never just read a single author, and allow yourself some margin for error. Some books from the 1600's may simply just not cut it today.

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