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Can someone ever say correctly, "I'm worried about him driving home so late at night alone without his phone"? Or should it be his instead of him. Does that construction always need to be possessive?

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  • That is correct. You can change/switch the structure a bit but that depends on your own taste or if you want to emphasize something. Who are you worried about? Him [doing something]. Commented Feb 24, 2017 at 1:44
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    You probably want a comma after night. "His" avoids an ambiguity because it makes clear that the whole sentence is about him. As is, it could be interpreted that it is you who is alone and without his phone.
    – fixer1234
    Commented Feb 24, 2017 at 1:49

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Your two sentences have different meanings depending on what you want to emphasize

I'm worried about him driving home
you are worried about the person "him".

I'm worried about his driving home
you are worried about his driving skills

both would be understood that you are worried if "he" will get home safely.

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