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How would I be making it his day by buying myself a new dress?

Tell me please what kind of grammatical structure is that?
Why -ing form is there?

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    Are you sure the original didn't say, "How would I be making his day...?" (i.e., no "it")
    – J.R.
    Commented Mar 19, 2018 at 14:10
  • Sure. The original didn't say, "How would I be making his day...?
    – Nadya Solo
    Commented Mar 20, 2018 at 11:52

2 Answers 2

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  • How would I be making it his day by buying myself a new dress?

The idiom is: to make someone's day. This can include it or not.

  • How would I be making his day by buying myself a new dress?

To make someone's day

Question form: Are you making (it) my day by [doing whatever]?.

You are making my day by [doing whatever].

You are making my day by giving me a compliment.

Giving me a compliment is how you are making my day.

So,

"Buying myself a new dress is how I am making his day".

Question form in the conditional:

  • How would I be making his day by [buying myself a new dress].

  • Would I be making his day if I bought myself a new dress?

How would x be [making etc.] is the conditional tense for this idiom, preceded by the question word HOW.

As in: How do you know that? How would you know that?

If I say: I'm going to make it your day. The it refers to the day. It would be the same as: I'm going to make this your day. It is not required but can be used.

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It strikes me as a mix between "make it his business" and "make his day".

So really the discussion here is this, and not so much the "would I be making."

To "make one's day" is to make a person happy for the entire day although this can also be used sardonically as well ("The rain messing up my near hairstyle really made my day.")

To "make it one's business" is to interest oneself in a situation or to suggest that a situation is of certain importance to that person.

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