These two words sound exactly the same to me. Are we assuming the "h" in "whine" is silent?


In common use, yes, whine and wine sound the same. That said, if you wanted to give attention to occurrences of /wh/ and carefully pronounce them as in "white," no one would object.

(And with that said, I can't help but think of Stewie and "Whil Wheaton.")


Absolutely the "h" in "Whine" sounds. For "whine" I make a breath sound followed by "wine", almost, "h' wine". Exactly as in "white". Same with "win" and "when", I pronounce "when" almost "h'win".

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