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In dictionaries, I often see examples using the structure "to have trouble with + a thing"

For example

He was having trouble with his homework.

We’re having a lot of trouble with the new computer system.

And, some native speakers say "I have trouble with my boss" is somewhat wrong or weird.

They insist on me saying "I am in trouble with my boss".

My question is:

  • is "I have trouble with my boss" wrong or not common?

  • if it is not wrong, then what is the difference between "I have trouble with my boss" and "I am in trouble with my boss"?

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You can say you have trouble with someone or something if that person or thing is causing you problems:

I'm having trouble with my car (it won't start, the brakes are bad, etc)

I'm having trouble with my son (he gets drunk a lot, he steals from me, he is lazy)

You say that you are in trouble with someone in authority over you if you have done something wrong, or are suspected of it:

I'm in trouble with the police (I got drunk and smashed some windows)

I'm in trouble with my boss (I was late for work three times this week)

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"I have trouble with my boss" is unusual but "I have trouble with my children" is common.

You generally say you have trouble with something or someone that's supposed to obey you (but doesn't - that's the aforementioned trouble). You're supposed to obey your boss, so you won't say this so commonly. You could say this to mean you find your boss hard to deal with, but it's kind of cheeky.

"I am in trouble with my boss" means your boss is angry with you (and possibly that you're facing the threat of some kind of punishment from them).

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  • I would understand 'I have trouble with my boss' to mean that you have a difficult relationship with them. Jun 12 at 8:40
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(A) The first definition for "in trouble" from the Farlex Dictionary of Idioms is

  1. Subject to punishment for a particular offense or wrongdoing.

Example: I am in trouble with my boss because I ate his hamburger when he wasn't looking!

(B) The definition for "the trouble with (someone or something)" is

The most irritating or troublesome aspect or characteristic of someone or something.

Example: The trouble with bosses these days is that most of them are lazy!

(C) The first definition for "trouble (someone or oneself) with (someone or something)" is

  1. To bother or inconvenience someone with something, such as a problem, question, or task.

Example: Don't trouble the boss with this right now. He's eating his hamburger!

Thus "I am in trouble with my boss (for spilling coffee on him)" implies that the boss is unhappy with you (A). Whereas "I have trouble with my boss (who is always so lazy)" means that you are irritated with your boss (B). So in case A, the boss has a problem with you, whereas in case B, you have a problem with the boss.

Links:

https://idioms.thefreedictionary.com/in+trouble

https://idioms.thefreedictionary.com/trouble+with

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