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In this answer I provided a sample sentence:

You are friend with Toby.

and as a result I received a comment from @JasonBassford:

*Both of your example sentences are ungrammatical. You can't be friend with someone. You can be a friend of someone or you can be friendly with someone.*

Now, I tend to trust JasonBassford (as a result of seeing hos posts here on ELL), but a dilemma remains.

From my point of view, friendship and friendliness do not convey the same meaning.

I can be "friendly" with a dog or with some foreigner on the street, but that will not make us friends. Friendship (from my point of view) is much deeper and much more complex than friendliness.

So, to be explicit: is there another way to express friendship? I feel that something is missing, but I am not sure what that is.

As one alternative, I think about "to be friends with" (friend + s = plural):

You are friends with Toby.

but I cannot decide if it is fine / idiomatic, or if there is something else missing.

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  • I don't know about other dialects, but in British English, we can use friendly with to talk about a relationship of friendship. I was friendly to a nice cat I saw in the street; I am friendly with Mary Smith; we have known each other since childhood. Jason Bassford's comment accords with this.
    – Michael Harvey
    Apr 22, 2019 at 7:35
  • Hmmm... That is interesting. However, I prefer to be as non-ambiguous as possible, and as you describe it, "to be friendly with" has some potential to transmit incorrect information (compared to the intention).
    – virolino
    Apr 22, 2019 at 7:39
  • Ambiguity? Friendly to is different from friendly with.
    – Michael Harvey
    Apr 22, 2019 at 7:42
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    You could also say You are Toby's friend. In fact, that's probably the most idiomatic. (Additionally note that friendship implies friendliness, although not the reverse.)
    – Jason Bassford
    Apr 22, 2019 at 7:55
  • 2
    Does this answer your question? Do "friend of" and "friend with" have the same meaning?
    – FumbleFingers
    May 11, 2021 at 16:53

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The key to understanding this is the preposition 'with'.

How many people are being talked about, one or two?

You are friends with Toby.

You are Toby's friend. Toby is your friend. Two friends.

It's not idiomatic, but rather the correct agreement.

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