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If I could have kept him away by paying money, I certainly would have paid money.

If I had kept him away by paying money, I certainly had paid money.

Thanks.

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    The second sentence does not make much sense. If you had paid him you should know - so if you don't know there needs to be some explanation. "If I had kept him away by paying him money, then it's likely I paid him."
    – Andrew
    Feb 15 '17 at 1:49
  • @Andrew Yes, you are right, that is a bad example.
    – user48367
    Feb 15 '17 at 2:01
  • @Andrew If I had received that present, I had been surprised. Is this OK?
    – user48367
    Feb 15 '17 at 2:14
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    Hypothetical / conditional statements usually require "would". "If I had received that present, I would have been surprised."
    – Andrew
    Feb 15 '17 at 4:11
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In practice, they're interchangeable in most cases. But there is a difference of nuance:

If I had kept him away ...

implies a straight factual "I didn't keep him away"

If I could have kept him away ...

implies more strongly that, not only did I not keep him away, I couldn't possibly do so.

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  • Thank you. And could you please answer my another question: In reverse, 'Could have I kept him away' and 'Could I have kept him away', which is correct?
    – user48367
    Feb 15 '17 at 1:44
  • 'Could have I kept him away' is certainly wrong. Could I have kept him away' would be OK as a question. That is: "Could I have kept him away?". Feb 15 '17 at 6:08
  • Could I have kept him away (but not could have I kept him away) is also a literary form of If I could have kept him away. I think that's what @user48367 meant.
    – Colin Fine
    Feb 15 '17 at 20:52
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If I could have kept him away by paying money, I certainly would have paid money.

This basically means:

If I could have (done something) then I certainly would have (done it)

So, for example:

If I could have ordered chips with my hamburger then I certainly would have ordered them.

The meaning basically is "I would do it if possible".


If I had kept him away by paying money, I certainly had paid money.

This is somewhat different. We are talking about what actually happened in the past (not what might have happened).

A reasonable sentence might be:

If I had seen that guy before, I certainly would remember his face.

Or:

If I had gone to the zoo, I certainly would have visited the lions.

The meaning here is "If (something had happened in the past) then (I would have done something)".

As it stands your second sentence doesn't make much sense. Maybe it could be reworded as:

If I had kept him away by paying money, I certainly would remember it.

Or, put another way:

He wanted money to keep away. I paid it.

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