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This discussion arose around the statement "PersonX was my oldest high-school friend" The intention was to refer to length of time known (roughly the opposite of 'most recent') as opposed to meaning that the friend was older in years (age).

After reading this thread on eldest vs oldest it seems that oldest would, indeed, by the right word to describe most-aged friend. Was the original statement incorrect? If so what is the proper term?

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The phrase is indeed ambiguous. My oldest friend usually means the one I have known longest, and it would be unusual to use it in the other sense, but it might happen.

There is not really a straightforward way of saying the other meaning: I would probably use eldest (which is only used in this sense), but my eldest friend, though clear, sounds odd to me, so I would say the eldest among my friends.

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You are right that is ambiguous. The difficulty comes because old here is being used as an opposite of new rather than as an opposite of young, but both meanings of the word "old" could be applied here in a way that would be valid.

We use context automatically to disambiguate in these situations, and there relatively few situations where you would care to be describing your friend who is the oldest age, so this doesn't tend to be confusing. "My oldest book" is much more ambiguous because it's easy to think of situations where you would be describing both the book you've had the longest and the book that was written/printed earliest.

If such a need did arise, you would say "the" instead of "my" (e.g. the oldest friend I have.) Logically, this could mean the exact same thing, but people would pick up the fact that you were using a different phrasing for a reason.

The web series Jake and Amir pokes fun at this ambiguity in the English language in Jake and Amir: Cheryl

Jake: Your best friend in the whole world? I've known Amir for 5 years, and I've just heard of you.

Cheryl: Yeah, we met yesterday.

Jake: You said you were his oldest friend.

Cheryl: I'm 50. Thank you for saying I look fantastic.

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Two suggestions:

  • My longest standing high school friend
  • My earliest high-school friend

The second option doesn't necessarily imply that you've been friends continuously: you could have lost touch in the meantime.

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The person who has been my friend over a longer time period than any other is referred to as my longest tenured friend.

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    Do friends have tenure? I can’t say I've ever heard it used in that sense. Commented Sep 11, 2022 at 5:58
  • Yes, friends do have tenure. Tenure includes "the term of holding something," per Merriam-Webster. My friends all hold a position of friendship with me. The friend in that position longer than any other is my longest tenured friend, unambiguously.
    – Habanero
    Commented Sep 19, 2022 at 13:38

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