Is it true that the current usage and spelling of words like we're/were, there/they're/their, your/you're, etc. is shifting? I heard that in the next generation the apostrophe may be disappearing in these words, the spelling changed, and the meaning made more fluid to circumvent the need for these homophones altogether.
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My professional sense is that it is not true that the apostrophe is endangered in any significant way. In fact, the popularity of online communication in text has led to a small resurgence of interest in style guides and usage manuals. (E.g., "Eats, Shoots, and Leaves.")
I wouldn't hold your breath for the atrophy of the apostrophe. HA! Sorry, I couldn't resist a little assonance and a near-pun.
In informal usage, these differences have been neglected often for some time. In formal usage, of course, contractions aren't very appropriate. There is the middle ground, though, of general writing that is neither chatty nor formal. In this middle ground, contractions are permitted, homophones often unavoidable, and good spelling very helpful for making one's point known.
Many of the people who can't be bothered to learn to spell correctly will not need to bother with making themselves clear about matters more pressing than who slept with whose girlfriend and who's going to the prom with whom, even after their thirtieth or fortieth birthdays. A rule or two about contractions and relative or possessive pronouns hardly seem too taxing. The only one that is counter-intuitive, in any event, is "its/it's."
If you think about it, "there" and "they're," for instance, really have nothing in common. The idea of picking a single spelling for both and letting context sort it out would cause more confusion than it would solve. I do admit that some of the other pairs do have more in common semantically, but the idea is still bad.
Those of us who wish to be understood correctly, the first time, will continue to belabor ourselves with spellchecker and a quick proofreading, and teach our children to do likewise. It is a bad policy to accommodate illiteracy too far. It doesn't matter much whether we bastardize our language out of sloth or accommodation for the slothful. It still ends up bastardized, and our ability to express ourselves truncated. Most importantly, we cannot think what we cannot speak. Words and thoughts go together, as the novel 1984 so astutely recognizes.
The spelling does change for some words over time, so it's very likely that some words that have apostrophes but doesn't need them will lose the apostrophe at some point in time. Components of a language that has no use tend to go away over time.
However, this will only happen for some specific words, not apostrophe use in general.
It's of course possible that apostrophes will come out of use entirely at some point, but by then the language around the apostrophes will have changed so much anyway that i's a moot point.