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"I was home-schooled in middle school, if that counts."

I think that without the comma, the sentence implies that the speaker was home-schooled in middle school only if "that" counts, whereas with the comma, the speaker is saying "if that counts" as more of an aside. I'm definitely going more for the latter meaning, so is the comma correctly placed, then?

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Yes. It's an example of parenthetical comma. If we instead use parentheses as in:

I was home-schooled in middle school (if that counts).

Then, there's a heavier sense of break and separation, but the meaning is close.

The parenthetical use gets hidden slightly, because we don't have a closing comma just before the period, which is to say it's logically the same as:

*I was home-schooled in middle school, if that counts,.

But whenever we might logically have ",." we just write "."

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Yes, that's a correct use of a comma to set off an aside.

If you leave it out, it looks like a simple (yet nonsensical) conditional.

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