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  1. I would only put a written note on a client's desk whom I know.

I may be criticised for assuming that the attachment of 'whom' to 'client' is understood and unambiguous. Grammatically, some might say, I am attaching 'whom' to 'desk'.

  1. I would only put a written note on a client's desk if I know them.

Similarly with the following :

  1. I would only drive a friend's car who had insurance.

  2. I would only drive a friend's car if he had insurance.

Am I wrong to use 1 and 2 ?

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  • Common sense trumps grammar.
    – Barmar
    Commented Jan 25, 2018 at 1:21
  • @Barmar We-ell ... if there is genuine ambiguity, common sense will not be certain what to do. Grammar requires to articulate properly so that sense may understand.
    – Nigel J
    Commented Jan 25, 2018 at 1:25
  • The point is that grammar may suggest two possible interpretations, but common sense indicates that one of them is not reasonable. So even though the grammar is ambiguous, the intention is not.
    – Barmar
    Commented Jan 25, 2018 at 1:33
  • Of course, if both possible meanings are possible, then we do have a true ambiguity. Then we usually need to reword.
    – Barmar
    Commented Jan 25, 2018 at 1:34

2 Answers 2

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I rather doubt we will encounter "the desk" as "whom" very often. Desks usually are not a "who". So, I doubt ambiguity.

I would prefer a different construction, however.

I would never put a written note on the desk of a client I did not know.

For me, that clarifies intent. But the whole business is mostly opinion, and mine is offered

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Regardless of the issue of ambiguity in 1 and 3, they both comes off sounding rather awkward. They would, however, suffice for colloquial use, but you would be better off refraining from such use in professional or academic writing.

I would only put a written note on the desk of a client whom I know.

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