1. What secrets of mine did you tell Tim, in case he hadn't already heard
everything from someone else before?

2. What secrets of mine did you tell Tim, assuming he hadn't already heard
everything from someone else before?

The speaker assumes that Tim might have heard all his secrets from someone
else before, and he is asking his interlocutor which of his secrets his
interlocutor divulged to Tim.

I suspect Tim has already heard everything from someone else, but anyway,
what secrets of mine did you tell him?

Are '1' and '2' grammatical and meaningful?

Gratefully,
Navi

Interested in strange structures
Lost in the twilight zone of the English language
Obsessed with ambiguity

Navi, I have rewritten your alternative to emphasize the
part that's different:

> What secrets of mine did you tell Tim,
> 1. in case
> 2. assuming
> he hadn't already heard everything from someone else before?
>
> The speaker assumes that Tim might have heard all his
> secrets from someone else before,

Yet he (the speaker) explicitly makes an opposite assumtion!

> and he is asking his interlocutor which of his secrets his
> interlocutor divulged to Tim.
>
> I suspect Tim has already heard everything from someone
> else, but anyway, what secrets of mine did you tell him?

No, that's a wrong interpretation, or a badly worded one.
It sounds absurd.

> Are '1' and '2' grammatical and meaningful?

I think both are grammatical, but only #2 is meaningful.
`in case' cannot be used to intoduce this sort of a
precondition for a question, cf.:

And what shall we do in case it rains

which is meaningful.

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Hi Anton,

24.12.2023 1:18:26, Anton Shepelev wrote:

> > I suspect Tim has already heard everything from someone
> > else, but anyway, what secrets of mine did you tell him?
>
> No, that's a wrong interpretation, or a badly worded one.
> It sounds absurd.

How is it wrong though? I believe it says the same thing just in a
slightly less formal way.

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not stopped."
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Gleb Hlebov to Anton Shepelev:

> > Navi:
> >
> > > I suspect Tim has already heard everything from
> > > someone else, but anyway, what secrets of mine did you
> > > tell him?
> >
> > No, that's a wrong interpretation, or a badly worded
> > one. It sounds absurd.
>
> How is it wrong though? I believe it says the same thing
> just in a slightly less formal way.

This a contradiction. The speaker suspects that Tim heard
the secret from somebody else, yet asks of his interlocutor
what part of the secret he told Tim. The original is not so
bad, because the stated suspicion is the opposite -- that
Tim did /not/ hear it from somebody else, in which case the
question is only natural.

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Hi Anton Shepelev,

29.12.2023 17:25:27, Anton Shepelev wrote:

> > > > I suspect Tim has already heard everything from
> > > > someone else, but anyway, what secrets of mine did you
> > > > tell him?
> > >
> > > No, that's a wrong interpretation, or a badly worded
> > > one. It sounds absurd.
> >
> > How is it wrong though? I believe it says the same thing
> > just in a slightly less formal way.
>
> This a contradiction. The speaker suspects that Tim heard
> the secret from somebody else, yet asks of his interlocutor
> what part of the secret he told Tim.

Well... It still seems logically consistent to me. I don't know how you
got the idea that something's "wrong" with it. The usage is just fine
like this and everyone's supposed to see the point.

Let's meditate:

"I guess he already knows everything...
as of now...
but... if anything...
what have you told him?"

Isn't it ok as well?

--
"The early worm deserves the bird."