Almost no one does it except professors and cosmopolitans. Though some books will say that "what" should be pronounced "hwutt" and not "wutt", is it really recommended for us, the common folk, to espouse this pronunciation; or would we sound affected in doing so?
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As others have noted, w(h)ether you should pronounce "wh" as /w/ or /ʍ/ depends on what the prevailing regional accent does. The big exception to this is singing; it pays to be fussy about pronunciation when you sing, even if you wouldn't in normal speech, because it helps the words to come through the texture.
Incidentally, you shouldn't think of /ʍ/ as sounding like "hw". /ʍ/ is an unvoiced aspirant made with the "w" mouth shape, not an /h/ followed by a /w/.
This question explains about its origin and usage. Basically, to sum up, "wh" was originally pronounced "hw" due to its origin.
As you can see, it was originally spelt "hw", changed to "wh", and now, its pronunciation is slowly changing to "w" due to a phenomenon called the "wine-whine merger":
As you can see by this image, that "wh" is stilled pronounced "hw" in quite a bit of USA.
It is true that "wh" is increasingly being pronounced "w", but that doesn't mean that pronouncing it as "hw" is "affected", or snobbish.
So, I wouldn't be bothered using either, as both pronunciations are actually acceptable.
It is regional. Its region is shrinking, but not yet zero. If no one does it where you live, then go ahead and say "wear you live" instead.
The goal of oral English is to be understood clearly in the initial iteration. If one wants to communicate 'where' something is located, aspirating the word clearly differentiates it from the word 'wear', as in reference to apparel. Ambiguity, repetition, and wasted time can thus be avoided. It is a matter of logic.
If you fail to pronounce the combined "wh" sound, how is a person to know if you mean "whale" or "wail", "where" or "wear", whether" or weather, etc. I am a singer, and diction is extremely important or those listening won't know which word you mean. It sounds like mush coming out. Do we really want to start speaking sloppy? I know "I" strive to make the distinction.
I think dropping the "h" is an embarrassing mistake.
protected by Mitch May 31 '15 at 17:03
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