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

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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.")

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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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