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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