a friend of my sister’s/a friend of my sister

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englishhobby

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Is there any difference in meaning in the following phrases? Are they equally natural?

1) He is a friend of my sister’s.
2) He is a friend of my sister.
 
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Neither is correct because they don't end with a full stop.
 
Is there any difference in meaning in the following phrases? Are they equally natural?

1) He is a friend of my sister’s.
2) He is a friend of my sister.

They are both natural. In number 1, the speaker is probably thinking that the sister has a number of friends. Number 2 doesn't suggest the sister has only one friend, but rather that the speaker doesn't have that number in mind.
 
Correct me if I'm wrong, but I've always interpreted those differently:

1) He is a friend of my sister’s. = This to me sounded like it was meant to be "He is a friend of my sister's friend."

2) He is a friend of my sister.
= "He is my sister's friend."
 
1) He is a friend of my sister’s. = This to me sounded like it was meant to be "He is a friend of my sister's friend."

No, 1 has never meant that.
 
He's a friend of my sister's is a simple and common way to express that among all of my sister's friends, he is the one I'm talking about.
 
In BrE, "He's a friend of my sister" and "He's a friend of my sister's" are fairly unnatural. Most of us would say "He's one of my sister's friends" or "He's friends with my sister".
 
I'm not surprised by your preference but I'm surprised that you don't like the "to be friends with someone" construction. It's very common for me.

I'm friends with lots of people from Europe.
My nephew is friends with the kid next door.
That guy over there is friends with my sister.
 
He's a friend of my sister's is a simple and common way to express that among all of my sister's friends, he is the one I'm talking about.

Not trying to argue here, but I'd just like to know if sister's is in possessive form showing possession, and if it is, what it is possessing. I mean, he is a friend of my sister's what? Sorry, I just couldn't wrap my head around why there's a need for the 's.

P.S.: I hope I'm not hijacking someone's thread.
 
I would say:

He's my sister's friend.
 
Not trying to argue here, but I'd just like to know if sister's is in possessive form showing possession, and if it is, what it is possessing. I mean, he is a friend of my sister's what? Sorry, I just couldn't wrap my head around why there's a need for the 's.

P.S.: I hope I'm not hijacking someone's thread.

Yes, it does express possession. It's a shorter way to say ​he is one of my sister's friends.
 
We cannot usually put a possessive between another determiner and a noun. We can say my friend, Ann's friend or ​that friend, but not [STRIKE]a my friend[/STRIKE] or [STRIKE]that Ann's friend[/STRIKE]. Instead we use a structure with of + possessive.


That policeman is a friend of mine.
He's a cousin of the Queen's.
How's that brother of yours?
She's a friend of my father's.

Swan, Michael (2005.418), Practical English Usage​, Oxford: OUP

I guess you're right. We can never say That policeman is a friend of me, or How's that brother of you? But if that is the case, shouldn't He's a friend of my sister be wrong?
 
They are both right.

Nobody said English was logical.;-)
 
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