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Re: I dislike him wearing a mask or I dislike his wearing a [#permalink]
I think it depends on what you intend to relay.

If you're saying that you dislike someone because he wears a mask, you use the first sentence 'I dislike him wearing a mask'.

The second statement is more appropriate when you are referring to his habit of wearing a mask. This habit belongs to someone, and so you use the possesive pronoun 'his'.
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Re: I dislike him wearing a mask or I dislike his wearing a [#permalink]
anirban16 wrote:
I dislike him wearing a mask or
I dislike his wearing a mask?


I think the second sentence is correct because the possesive adjectives (e.g. my, your, his, her, its, our, their etc.) precede the gerund. for example:

1. He insists on you leaving the town- is not correct.
2. He insists on your leaving the town - is correct.

Him is one of the complement pronouns (e.g. me, you, him, her, it, us, them etc.). Complement pronouns take complement position and complement a verb or a preposition. for example:

Uma told him a story.
Ram gave me a pen.
Ram will present his after him (Shyam).
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Re: I dislike him wearing a mask or I dislike his wearing a [#permalink]
I would choose the second too, although I agree there may be circumstances where you can use a structure like the first one.
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Re: I dislike him wearing a mask or I dislike his wearing a [#permalink]
anirban16 wrote:
I dislike him wearing a mask or
I dislike his wearing a mask?


I dislike him who wears a mask ==>I dislike him wearing a mask.

Could we say that?

I dislike his wearing a mask.

'wearing a mask' is the gerund as the object of possessive.
right?

Need more explanation.
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Re: I dislike him wearing a mask or I dislike his wearing a [#permalink]
chunjuwu wrote:
I dislike him who wears a mask ==>I dislike him wearing a mask.

Could we say that?



I don't think so. If in your first example "him" is "the person", as "I dislike the person who wears a mask" then it can be changed to" I dislike the person wearing a mask". Here wearing a mask modifies the person and defines the target of your dislike. However "him" is already defined, you can't modify it using a clause or a particle.



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Re: I dislike him wearing a mask or I dislike his wearing a [#permalink]
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