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1) He gave me five hundred dollars to take care of his dog.

I think there is a weird kind of ambiguity in that sentence. One idea is obviously that he paid me so that I would take care of his dog.

The other idea is (very unlikely but possible):

2) He gave me five hundred dollars to take care of his dog with.

In this case, the money doesn't go into my pocket. He isn't paying me anything. I am probably taking care of his dog as a favor. The money is to be spent on the dog,

Is there ambiguity or not?

Gratefully,

Navi

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Hi, Navi,

@navi posted:

1) He gave me five hundred dollars to take care of his dog.

I think there is a weird kind of ambiguity in that sentence. One idea is obviously that he paid me so that I would take care of his dog.

The other idea is (very unlikely but possible):

2) He gave me five hundred dollars to take care of his dog with.

In this case, the money doesn't go into my pocket. He isn't paying me anything. I am probably taking care of his dog as a favor. The money is to be spent on the dog,

Is there ambiguity or not?

Gratefully,

Navi

I agree that this could be ambiguous. I think it depends on the question, ''who is me?'' A close friend (doing it as a favor) or a pet sitter (doing it as my job). 

Last edited by ahmed_btm

Hello, Navi—I agree with you and Ahmed that the sentence can be ambiguous in the interesting way you have pointed out, and think that, syntactically, the attachment site of the infinitival clause will be different in each case. In practice, however, it is context that will make the difference:

  • He gave me $500 to take care of his dog. How could I refuse?
  • He gave me $500 to take care of his dog and $50 to take care of his bird.

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