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If one were literally in water over one's head, one would, even if a great swimmer, after awhile, drown.

To be in over your head means that you are floundering, doing something beyond your capabilities, that, unless the situation changes, will result in a catastrophe for you.
It means he is in more difficulty than he can manage and can't handle the situation. For example: John was in over his head looking after the 10 children Trevor was in over his head because of the amount of work he had to do before his deadline
It means that you don't really know what's going on. You don't know exactly how to handle the situation. It also means that the situation could be too much for you.
Its above his understanding or he did not grasp the meaning.

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Q: What does to be in over one's head mean?
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