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Originally Posted by 26 Year Gap
In this instance, Mr. Annoying Spelling guy would not come into play as the spoken word is the same for both your and you're.
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Mr. Annoying Etymology Guy has to disagree. When spoken, 'your' and 'you're' are homynyms. They may be pronounced the same way, but they are definately different words.
In addition, once the words are written out, the difference comes into play.