1

Context:My friend was disturbing me by messing around in English class; running, speaking aloud, etc. I told my friend to sit down several times, but he didn’t sit down.

  1. How much did I tell you?
  2. How much should I tell you?
  3. How more should I tell you?

What is the most natural one to English speakers? I think I can be rude because he is my best friend.

5
  • None are very natural. You are asking a rhetorical question. You don't want your friend to tell you an answer to the question.... How rude do you want to be? Why are you telling your friend to sit?
    – James K
    Apr 10 at 9:00
  • James K, I think I can be rude because he is my best friend.
    – user133899
    Apr 10 at 9:03
  • Okay Why are you telling your friend to sit in English?
    – James K
    Apr 10 at 9:04
  • 1
    Because he was disturbing me by messing around in English class; running, speaking aloud, etc.
    – user133899
    Apr 10 at 9:05
  • Good, I'll add that context to the question
    – James K
    Apr 10 at 9:07
2

None of these are natural.

Probably you want something like

How many more times do I have to tell you [to sit down]?

You use "many" because you are asking for a counting number. The word "times" is countable. "How many times" is a common phrase. I've used "have to" as this is less formal than "must".

This is a rhetorical question. You don't want your friend to tell you the answer "You have to tell me three more times."

There are other things you could say.

How many times have I told you [to sit down]?

Do I have to tell you again?

I'm not going to tell you again.

This suggests that next time you will take action!

It is always going to be a bit rude to talk to someone like this. Whether this is okay depends on your relationship. It might be hard for a language learner to judge rudeness.

6
  • Is it okay to use adverb ‘much’ modifying ‘more,’ of course not adjective ‘much’?
    – user133899
    Apr 10 at 9:15
  • Yes. "much more" is very natural. But "much more times" is not correct, because "times" is countable. It must be "many more times" ... "How much more ice cream is he going to eat?"
    – James K
    Apr 10 at 9:17
  • I think it is related to British culture. In my mother language, we choose 2 for half and 3 for the other half; I may be confused because in my native language the word that equals to ‘how’ can modify the word that equals to adverb ‘more’. I think British speakers tend to leave out unnecessary parts.
    – user133899
    Apr 10 at 9:29
  • We could also say "How many times have I told you [to sit down]?".
    – rjpond
    Apr 10 at 9:33
  • Yes, this again illustrates that English is not the same as other langauges! I don't see any special British/American difference here.
    – James K
    Apr 10 at 9:35
1

I told my friend to sit down several times, but he didn’t sit down.

There seems to be an error of misplaced modifier; I believe you mean

I told my friend [several times to sit down], but he didn’t sit down.

You have not told us your intention, but if it is to urge your friend further, you could say

How many more times must I tell you?

1
  • It probably wouldn't suit OP's exact context here (where the repeated requests all seem to have been made on the same occasion), but if this sort of thing had happened several times in the past, rather than all on the same day - I've told you time and again to sit down and be quiet! Apr 10 at 12:27

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