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For example, can you say 'I have more than one best friend' and is that grammatically correct given that these friends are equally good?

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I see nothing wrong with talking about your best friends or the worlds highest mountains, but that does not imply that the actual top-position is shared by two or more of them. –  oerkelens Jun 3 at 13:29
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This is not a matter of grammar. You can say that you have more than one best friend and be completely grammatical. You can also say that you have more than one best pelvis and be grammatical, even though you obviously have only one pelvis. What you’re asking about is logic and semantics; not grammar. –  Janus Bahs Jacquet Jun 3 at 13:30
    
If you are really asking if it's grammatically correct, then the answer is that you can put absolutely any adjective at all there. The grammar does not change one bit. –  RegDwigнt Jun 3 at 13:33

1 Answer 1

The term best is a category. How many units fit in the category depends on context.

If there is a contest, like a dog show, there may be a best in each breed, and a best in show. Overall, the show would issue several best medals.

Stores often categorize products based on features. They may label several of a given type of item good, several better and several best. Whether they have one or more in each category mostly depends on the depth of their offerings.

The term best when applied colloquially is a high end compliment, not intended to formally rank a person with regard to all friends or aquaintences. It is likely that your spouse would not be annoyed or feel diminished if you thank a friend for an assist by saying

You're the best!

As to best friend, it again depends on context. You might say

We're the best of friends.

There may be several individuals you could say that about without confusion.

However, when you say

This is my best friend

most US speakers would probably think that the identified individual was likely the single person you felt closest to (aside from relatives, who might or might not be labeled best friends).

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