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My friend, Yong, kept telling me that the above construct must be used since man's represents a set of friends that the man has. I believe he went too far.

I understand double possessive is sometimes required to help clarify the difference between a set from its subset / element.

For examples:
1. John met only one friend of mine, where mine is a set of my friends and John met only one specific friend out of the set.
2. John borrows a picture of Bob's, where Bob's represents a collection of pictures that Bob has (e.g., that one picture could be the picture of Bob's car).

The second statement must be written that way to differentiate any picture that Bob owns from a picture that shows Bob's image. However, John met a friend of the man's could be logical and grammatically correct, but its double possessive usage is unnecessary since no possessive distinction is required.

After listening to my argument, Yong trapped me, "Do you think John met a friend of me is correct?"

Could you kindly share with me your thoughts?

Thanks and Best Regards,
Hoa Thai
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There are three ways to convey the idea you want here.

met a friend of mine / *met a friend of me / met one of my friends

met a friend of John's / *met a friend of John / met one of John's friends
?met a friend of the student's / ?met a friend of the student / met one of the student's friends

*ungrammatical for the intended reading
?questionable; unnatural; unidiomatic -- but understandable

The first of the two is most frequently used for pronouns (mine, yours, ours, his, hers, theirs) and proper nouns. It is somewhat unidiomatic for other words.
The second is sometimes used though it is not often the best choice. It is clearly ungrammatical for pronouns.
The third is natural in any case and is probably the most usual in ordinary conversation. My advice: When in doubt, use this third form.

CJ
Comments  
Hi Hoa,

I guess that your friend, Yong is right. You can use double possessives to help clarify the difference between a set and its subset. However, the sentence:

John met a friend of me.

is not correct. This is because "me" is not a possessive form.
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Neeraj JainHi Hoa,

I guess that your friend, Yong is right. You can use double possessives to help clarify the difference between a set and its subset. However, the sentence:

John met a friend of me.

is not correct. This is because "me" is not a possessive form.

Neeraj,

My 2-cent:
Preposition of can often replace the possessive case. Thus, John met a friend of the man is good enough - no need for double possessive usage. John met a friend of the man's doesn't sound natural to me and not needed because both statements mean the same w/o causing any confusion.
 CalifJim's reply was promoted to an answer.
Dear Neeraj Jain and Anonymous,

Both Yong and I understand the need for double possessive usage. The difference between the two of us is that Yong insisted that the construct must always be used; while I believe it is applicable only for the cases where confusion might arise, but not always (why double when single is fine?). As pointed out by Anonymous, there is no confusion in the statement John met a friend of the man. However, the statement John borrows a picture of Bob deals with any picture with Bob's image; while the statement John borrows a picture of Bob's addresses any picture that Bob owns, including those with his image.

Of course, when Yong asked me if John met a friend of me is correct, we both knew that good English writers hate that statement, even though they accept both friend of Bob and friend of Bob's. The reason I said that Yong trapped me is because I don't see anything wrong with friend of me or picture of me, or any ... of me logically, even though I rather say my friend, ... instead.

Could you see now why Yong punched me with his question? He forced me to go with John met a friend of mine, so his argument for double possessive would stand. I still think he went too far but I have not found a good counter punch yet. I guess I must learn to love the language for its inconsistency to gain its idiomatic beauty! (Could the lover of yours be a friend of mine).

Cheers,
Hoa Thai

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Thank you CJ! - Hoa Thai