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1 I wouldn't be your friend unless I said that to you (one hour ago).

2 I wouldn't be your friend unless I had said that to you (one hour ago).

3 I wouldn't be your friend if I hadn't said that to you (one hour ago).

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The content of these sentences is a bit strange, which distracts from your question. The use of "unless" is awkward. (3) is OK grammatically, but if you're just looking at the grammar, it would be better to choose a more "normal" example, such as e.g. "I wouldn't be here if you hadn't telephoned me".

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To be honest, I see nothing strange in the content, even leaving aside the fact that a similar sentence was uttered in the American serial "The friends". The sentence was 1 (if I didn't mishear it). I am interested in the UNLESS versions. But thank you for pointing out that three is OK.

TicceTo be honest, I see nothing strange in the content,

I agree with GPY. The content is baffling. Perhaps in the context of a lengthy dialogue, it would make sense, but not as stand-alone examples.

The other thing obfuscating the meaning is the multiple negatives.

I wouldn't be your friend if you hadn't apologized.
The web site would have worked if you had accepted cookies.
The web site won't work unless you accept cookies.

Thank you, but I don't agree with both of you about the oddness of the content of the sentences. However, it's not really important. The important thing is that you replaced UNLESS with IF and by doing so you focused on the wrong thing. I will take your example and revert the needed patterns back.

I wouldn't be your friend (now) unless you apologized 20 minutes ago.

I wouldn't be your friend (now) unless you had apologized 20 minutes ago.


I would really appreciate it if you didn't modify them and comment on them just the way they are. Even if they don't sound idiomatic or whatsoever. What I want to figure out is the usage of UNLESS with past simple/perfect.

Thank you.

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TicceI would really appreciate it if you didn't modify them and comment on them just the way they are.

I wouldn't be your friend (now) unless you apologized 20 minutes ago.

I wouldn't be your friend (now) unless you had apologized 20 minutes ago.

Comment: I cannot compare them grammatically because they are incomprehensible.

TicceI wouldn't be your friend (now) unless you apologized 20 minutes ago.
I wouldn't be your friend (now) unless you had apologized 20 minutes ago.
I would really appreciate it if you didn't modify them and comment on them just the way they are.

To me, these sentences are just confusing. Did the other person apologise? We don't generally use "unless" to talk about something that is known to have happened in the past. "unless" can be used in connection with an uncertain past event, e.g. "I expect she's really mad at you -- unless you apologised?" (the speaker doesn't know whether the other person apologised).

Take the last one and think about it.

"I wouldn't be your friend if I hadn't said that to you (one hour ago)."

Why would you be his a friend?

Because you had said that to him.

Based on that concept, friendship would be pretty easy to you. You would consider someone a friend only if you told him before the statement "You are my friend".

You might use another sentence:

I wouldn't say that to you if you were not my friend.

Here, you tell someone something and that thing you would only say it for the persons who you consider them friends.

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"Why would you be his a friend?"

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