1. I don't want to be with the man always begging me for money.
2. I don't want to be with him always begging me for money.
Q1) Are both sentences above correct and natural?
Q2) Is "always begging me for money" referring to "the man" in each sentence?
I'm not sure whether "the man" and "him" play an important role in making a sentence natural or not. I don't think 2 is correct because "him" is already specified.
1. I don't want to be with the man always begging me for money. 2.
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1. I don't want to be with the man always begging me for money.
2. I don't want to be with him always begging me for money.
Q1) Are both sentences above correct and natural? No. It's more natural and clearer to say eg
3. I don't want to be with him (or the man) because he is always begging me for money.
Q2) Is "always begging me for money