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The man regarding whom we didn't know how many times he had been divorced left the room.

Is the above sentence grammatical?

We didn't know how many times one of the men present had been divorced. That man left the room. The man regarding whom we didn't know how many times he had been divorced left the room.

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    It may be grammatical, but it's a very clumsy and unnatural sentence. Mixing a clause about his marital history with a simple statement about his leaving the room reads very oddly. Dec 8 '20 at 9:09
  • Thank you very much, Kate. I see your point. But how about: "The business man regarding whom we don't know how much money he owes has applied for a big loan." Now the ideas hare a logical relationship to each other, but is the sentence natural?
    – azz
    Dec 8 '20 at 11:14
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    It would still be better as two separate sentences. "That businessman has applied for another big loan. We don't know how much money he already owes." Dec 8 '20 at 15:35
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I think the original sentence is technically grammatical, but as Kate Bunting's comment said, it is poorly written. It might make sense if there had been a previous discussion about the man's marital history, but then a shorter phrase referring to the discussion would be better. In the construction "The man who X left the room" the purpose of mentioning X is to identify which man left the room. a long complex clause does ntoi serve this purpose well, especially if it is about an uncorrelated topic. If the information about the divorces is relevant, it should be presented in a separate sentence or group of sentences, and then a short reference made to that discussion when saying that he left the room.

One possible version would be something like:

Joan pointed out a man, that had been reported as having been divorced more than once. I asked ho many times, but she wasn't sure. As we were talking about him, the man left the room.

This adds additional information (which I simply made up) but something like this, in which the information about the mari8tal history is presented separately from the information about the man leaving the room, would be a significant improvement.

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