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It's redolent of its age, but drives me nuts. Personally, I'm thankful for orthoepic reforms.
English is certainly less wild and wooly than it was, but the French would rightly sneer at this notion that our (frankly demented) orthography is especially consistent.
Oh it drives me nuts too. Maybe that's why I dig it. It's an intellectual exercise. Is that a long s or an f? Yeah.
I tried to read Canterbury Tales in its (semi-reconstructed) Middle English years ago. Your longanimity exceeds mine by leagues.
It's really interesting to compare the evolution of our languages across the ages, I think the earliest de facto Portuguese text I found was from the twelfth-century and it's completely readable, especially if you also know a bit of Spanish. I would say that Galician it's pretty close to what Portuguese was at that time, I mean, we were Galician-Portuguese after all
and even before that we had vulgar Latin which is also surprisingly understandable
What's also remarkable is the persisting mutual intelligibility of those, along with Fala and Eonavian. Then compare them (and esp. their grammar) to Catalan....!
Considering that its incomparably immane lexicon eventuated mostly from amalgamation and agglutination, the convoluted developments of English diachrony seem almost modest. After the slow merger of Anglo-Saxon with Anglo-Norman, vast lexical influxions from 20+ languages over not quite a millennium resulted in less inflectional reduction than that of simpler languages (as Mandarin) over half that span.
All latin based languages are in a certain way highly mutually intelligible, at least textual form. with the exception of Romanian I think, that became a Slavic romance language of sorts. I was reading about this interesting constructed language called Romance Neolatino, It sounds soooooooo good and it's highly intelligible for romance speakers. I hope it gets some attention
Admittedly, Neolatin is appealing and agreeably dulcet -- much better than Esperanto! Romanian's grammar (notwithstanding enclitic definite articles) and verbal vocabulary are impeccably romance, but that Slavic influence in its nominal vocab. and phonology is unshakable. Nota bene: Romanians only fully jettisoned Cyrillic a century ago.
Your mention of mutual intelligibility reminded me of an amusing moment from "Sleuth," which I recently reviewed. Late in the third act, Michael Caine proffers a clue in Italian to frantic Laurence Olivier, who despises Italians but is conversant in Latin, by which he fenziedly deciphers the hinting epigram by tracing its cognates. >:P