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I was chatting with my friend and I asked him this question. But, then I was not sure if it was grammatically correct because I had never used the phrase "do you think" with an interrogative sentence.

Here is the simple interrogative sentence:

Which day should I tell him to drop the package?

Now, if we add the phrase "do you think" in this sentence, does it change the subject- verb order (as in 1)or does it remain the same as before (as in 2) ?

1) Which day do you think I should tell him to drop the package?

2) Which day do you think should I tell him to drop the package?

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3 Answers 3

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When a wh-question asks about an object or a complement, a helping verb/modal verb follows the question word:

What did you say? Answer: I (subject) said (verb) nothing (object)

Where is my car? Answer: Your car (subject) is (verb) in the garage (complement)

Where can I sleep? Answer: You can sleep in my bedroom.

In your sentence, which day asks about the object of the verb think - a simple present verb that requires do or does in question:

Which day do you think bla bla? Answer: I think Friday is blah blah.

Bla bla has no effect on the structure of the question, and so bla bla must not be inverted. That means you can't invert should and I: Which day do you think should I ..? is incorrect. You can substitute blah bla with anything

Which day do you think he will come over? Answer: I think Friday is the day he will come over.

Which day do you think I should tell him? Answer: I (subject) think (verb) Friday (object) is the day you should tell him.

To see that I should tell him has no such effect, change the verb think into some other verb that needs no further complement:

Which day do you perform? Answer : I perform on Friday.

If you remove do you think, then you'll be asking about the object (or rather complement) of the verb should:

Which day should I tell him? Answer: You should tell him on Friday.

PS. In question, the verb goes before the subject

Which day should I?

in present/past simple tenses, there are no helping verbs and therefore we add the words do/does before the subject, in questions:

I respect my mom. Question : Who do you respect?

I think you should tell him on Friday. Question: Which day do you think I should tell him?

It's important to understand that Which day do you think I should tell him? and Which day should I tell him? are two different questions asking about two different things

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  • Thank you so much for explaining in such detail. I really appreciate it. But, I didn't mean to ask about the effect of the "bla bla bla" part of the sentence to the rest of it. What I meant to ask was would the addition of the phrase "do you think" in the original simple question "Which day should I tell him..." invert the order of "should" and "I"? The question in its simplest form has the order of first "should" then "I". What will happen if we add another question phrase like "do you think" in this question? Will it reverse the original order of of "should I" to "I should".
    – Shivam
    Sep 21, 2018 at 19:48
  • I addressed that already when I said "and so Bla bla must not be inverted". See above for an expanded answer.
    – Sara
    Sep 21, 2018 at 20:13
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In American English you will hear both:

Which day do you think I should tell him to drop off the package?

Which day do you think should I tell him to drop off the package?

We would say "deliver" or "drop off", not simply "drop".

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  • What if it's not "tell" but "ask" as the verb in the sentences? Does that make any difference?
    – Shivam
    Sep 21, 2018 at 19:19
  • That would make no difference.
    – TimR
    Sep 21, 2018 at 19:19
  • Is it common for native speakers to use "which day" when they want to know when something is going to happen. "Which day" sounds a bit different. I might be wrong but just wanted to confirm.
    – lea
    Sep 22, 2018 at 22:57
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    @lea: In response to a statement like "We are meeting to discuss the marketing strategy" native speakers might ask What day is that meeting? or When is that meeting? or some might ask a little elliptically Which day is that? That question means "Which day is that [going to take place on]?"
    – TimR
    Sep 23, 2018 at 14:26
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1) Which day do you think I should tell him to drop off the package?

Comment: The "do you think" is part of sentence as **in: Do you think I should tell him?. think is made interrogative: do you think. "I should tell him" is a separate clause and the object of "Do you think".

2) Which day should I tell him to drop off the package, do you think?

Comment: The question is: "Which day should I tell him?" The verb is should tell and requires reversal for a question if it is the main verb.

"Do you think" is an extra phrase. It is not an integral part of the sentence in 2). The comma above make now make that clear.

1) integrates the phrase and 2) does not.

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  • Just to make sure, we have the simple interrogative sentence without the "do you think" part : Which day should I tell him to drop off the package? Now, if we add the "do you think" part to the original question, will we have to change the original order of should and I? Does the addition of "do you think" in the original simple question change the regular order of firstly "should" then "I"?
    – Shivam
    Sep 22, 2018 at 6:07
  • Thanks very much for bearing with me. I really appreciate it. You are right when you say no, we don't invert the order of "should" and "I". But that's the case when you add that phrase in the end of the main question (as in 2). But, you did reverse the the order of "should" and "I" in (1) when you added the " do you think" part in the begining in the first example. I mean "reverse" or "swap" by taking " Which day should I tell him to..." as the base. Because for interrogative sentences we use the verb before the subject. I am taking that as the base and then adding the "do you think" part.
    – Shivam
    Sep 22, 2018 at 13:51
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    @Shivam You said: ["Which day should I tell him to drop off the package?" Now, if we add the "do you think" part to the original question, will we have to change the original order of should and I?] Your original order in that comment is: "should I tell him". If you add "do you think", you do not reverse that order.
    – Lambie
    Sep 22, 2018 at 14:21
  • Yes, you made that very clear. You didn't change the order as is clear from your second example. But, that's when you added it at the end after the comma. And I'm not asking about that example. I'm asking about your first example where you added "do you think" just after "which day", and in that case you did change the original order of should then I. Could you please talk about the first example as to why when we add the "do you think" phrase in the begining it reverses the original order of "should I tell" to "I should tell".
    – Shivam
    Sep 22, 2018 at 15:30

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