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1)
a) What did you want to talk to me about?
b) What did you want to talk about to me?

2)
a) Who do you want to talk to about this problem?
b) Who do you want to talk about this problem to?

I saw 1a in the TV show Grimm and the sentence set me thinking and there you go. I know sentences usually end with a preposition in English. Therefore 1a and 2b should be correct. However we've got 2 prepositions in each sentence so I'm not sure what to do and which ones would be correct. Maybe they all are. To my mind, 1a and 2a sound better but that's all I can say. How flexible is that kind of structure?

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    How about 2) To whom do you want to talk about this problem?? – Chris H Nov 12 '13 at 12:29
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    @Chris: yeah, except that's something exactly zero people ever will actually say. What they'll do instead is get the "Who do you want" out of their way first, on complete autopilot, and then figure out the rest later as they go along. The question is, what is it they are most likely to end up with. – RegDwigнt Nov 12 '13 at 14:24
  • @RegDwigнt You're saying that all of them are equally fine and natural? ) – Dunno Nov 12 '13 at 14:28
  • I'd feel hard pressed to find a point in my comment at which it was my intention to express or imply any such thing. ) – RegDwigнt Nov 12 '13 at 14:31
  • @RegDwigнt this > The question is, what is it they are most likely to end up with. :P :D Anyway I was sort of just asking your take on this. – Dunno Nov 12 '13 at 14:34
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I think "Who did you want to talk to about this problem?" is really the common "Who did you want to talk to?" ending in your desired preposition. The about part is kind of a tack on.

If you stepped up to an imaginary customer service counter where you could arrange to speak to a number of representatives, the reception person would say "Who did you want to talk to?" (2a) The about part would be implied or understood.

I think both 1a and 1b are probably both technically acceptable but 1b and 2b are both stilted and just nothing I would ever expect to hear in regular speech.

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