Motivated Grammar provided an excellent discussion of word choice — specifically confusing homophones (like “your” and “you’re”).
Let’s kick off the review session by addressing a confusion that will get you relentlessly and uninterestingly mocked: homophonic pairs. These are pairs like your and you’re or affect and effect, which are pronounced the same but spelled differently. Even if you know the difference between them, you’re still going to screw them up occasionally, especially in quick emails or when you’re writing with your attention wandering. (I probably type the wrong one about 1% of the time, which doesn’t sound like too much until you think about how often one of these words gets used.)
I’m going to look at a subset of these homophonic pairs here, the ones where one member of the pair is a contraction. These are the aforementioned your/you’re, as well as their/there/they’re, its/it’s, and whose/who’s.
In all four of these cases, the word with the apostrophe is the one…
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Pros Write 
I defiantly enjoy this post.
Wait … defiantly and definitely aren’t homophones — just another effect of the Spell Check Trap.
Ha! I have certainly been called “defiant” before. But it’s not true at this specific moment. Or in response to this specific post. Though Jack Black could be implicated here. I can’t blame spell check. Just clumsy typing on my part. (I had to re-type after the system kicked me out ’cause it didn’t like my log in ID.) Argh . . .