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

On Sunday, December 24, 2023 at 2:28:41 AM UTC-8, arthurvv vart wrote:
> 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

Both your sentences '1' and '2' seem a little awkward and clucky to me but I prefer your "2" over your "1".

Because grammar to me is always a secondary consideration to an intuitive and predictable flow and style, I would edit your #2 to either A, B or C as follows:

A - "What secrets of mine did you tell Tim assuming he hadn't already heard everything elsewhere already?" (where repetition of 'already' is intentional)

B - "What secrets of mine did you tell Tim assuming he hadn't heard everything elsewhere already?"

C - "What secrets of mine did you tell Tim assuming he hadn't already heard everything elsewhere ?"

Lo, on the 12/24/2023, arthurvv vart did proclaim ...
> 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?

Both are grammatical, I guess, but both are quite unwieldy and not
likely to be found in the wild.

"Which of my secrets did you tell Tim? Had anybody else told him?"

> Gratefully,
> Navi
>
> Interested in strange structures
> Lost in the twilight zone of the English language
> Obsessed with ambiguity

The only ambiguity I can force onto the originals is whether the
listner

--
"Maintaining a really good conspiracy requires far more intelligent
application, by a large number of people, than the world can readily
supply."

Sam Plusnet

Snidely explained on 12/24/2023 :
> Lo, on the 12/24/2023, arthurvv vart did proclaim ...
>> 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?
>
> Both are grammatical, I guess, but both are quite unwieldy and not likely to
> be found in the wild.
>
> "Which of my secrets did you tell Tim? Had anybody else told him?"
>
>
>> Gratefully,
>> Navi
>>
>> Interested in strange structures
>> Lost in the twilight zone of the English language
>> Obsessed with ambiguity
>
> The only ambiguity I can force onto the originals is whether the listner

... is covering the possibility that Tim /hadn't/ heard the secrets,
or the speaker is covering the possibility, which only makes sense if
Tim was supposed to hear.

/dps

--
"I am not given to exaggeration, and when I say a thing I mean it"
_Roughing It_, Mark Twain