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What is the difference in meaning between "careful to" and "careful of" in the following sentences?

Be careful to keep her shoes clean.

Be careful of keeping her shoes clean.

Does "Be careful to keep her shoes clean" mean "You should keep her shoes clean" ?

Does "Be careful of keeping her shoes clean" mean "You should not keep her shoes clean" ?

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"Be careful of keeping her shoes clean" literally means "There are dangers of keeping her shoes clean and you should be cautious about them." But I have never heard it said by people who intended it that way. Every time I have heard that statement made, the person had intended to mean "Make sure she doesn't get her shoes dirty."

As user514428 said, normally careful to is a reminder to make sure something is done, and careful of is looking out for a hazard. But you should also be aware that be careful of is often used in the incorrect manner in which your second example uses it. Humans are not always the most logical thinkers and thus not always the most logical speakers. This is commonly evident in English usage. My studies of other languages never really got anywhere, but I'm pretty sure it's also true for German, Spanish, Latin, Italian, French, and Japanese. I would guess it's true for all of the languages we've made to communicate with each other.

I've been told that it's just a matter of considering what would be reasonable for the sentence to mean. For example, in this case, it would be reasonable to assume that the girl's caretakers would not want the shoes to be dirty, so it's probable that they're trying to warn against them getting dirty. However, I've met enough people to know that while that works in this case, different people are sufficiently different that it doesn't work in all cases.

  • May i ask you a question? What is the meaning of "what you asking it is" in the sentence, " "Be careful of keeping her shoes clean" is literally what you're asking it is "? Strangely, for me, this sentence is not interpreted well. Is this sentence structure(what+subject+~ing+it+is) correct in English grammatically? – user22046 Feb 3 at 0:41
  • It is grammatically correct, but the literal semantics of the statement are the opposite of what people have meant by it 100% of the time I've heard it. I'll edit my answer to try to make it more clear. – Ed Grimm Feb 3 at 0:53
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Careful to is referring to doing something as in a precaution while careful of is to be aware of a hazard of some sort. Be careful of the bottom step it is crooked. Be careful to watch your step because the bottom step is crooked.

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