I think that there's a fine balance of recognizing modern colloquial usage while respecting historical meanings, and like you said, to a large degree it depends on the context. In my opinion, when you're in an informal context, such as chatting (I'm talking about face-to-face here--none of that lame IM stuff), emailing, etc., you can pretty much say things however you want. However, when you are in a formal context, it's important to be a little more articulate and observant of correct grammatical principles. Certain things, like formal letters, job applications/interviews, and most books, just don't call for "Yo, 'sup?" language. In any case, I think it's important that everyone know the rules of "grammatical" English, so that they can appear polished when necessary.
Some people say, "Well, if it's commonly accepted, then it becomes correct." I agree with that in many cases, i.e., you shouldn't say, "I certainly feel gay today," when you're trying to say you're in a good mood. Here are a few examples of when I will always disagree with that rule. 1) Spelling errors and homynyms. They're, their, and there are different things, and just because everyone writes, "Theirs a great restaurant over there," doesn't make it moral. Same goes for its and it's. 2) I'm not sure what to call this type of abomination, but you often hear people confusing long words that sound alike and using them in the completely wrong context or pronouncing/spelling them completely wrong. The Priesthood never was and never will be "patriartical." You often hear people say in ordinances that they're "confirming" the Melchizedek Priesthood when they mean to say "confer." That's just plain wrong, and no amount of common usage will change that. I think this type of mistake happens most often with mis-quoted cliches. I could come up with tons of examples, but here's just one more: When you're talking about something that can catch fire, the correct word is technically "inflammable." Over the years, the word "flammable" has come into existence, and in my opinion, it's used commonly enough that it's now a correct word in and of itself. However, when people say that something that cannot catch fire is "inflammable," that's grossly wrong. I don't care how often people do it, it should never be accepted as correct. My final pet peeve is when people pronounce the Biblical spelling of the word "shew" as "shoe." "Shew" is pronounced "show" (as it is simply an archaic spelling of that word), and I think that that mistake is involved with a lot of people not understanding the scriptures. Anyway, just because a word ends in "ew" doesn't mean it's an "ue" sound. The only people that sue their clothes when they fall apart are SCO executives. Everyone else sews them. Anyway, there's my little rant. It's horribly off-topic, but I think it's pretty interesting stuff.
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