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Is there any difference between the following expressions? When do I have to use one over the other one?

A:私に消しゴムを借りさせて下さいませんか。

B:私に消しゴムを貸して下さいませんか。

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B:私に消しゴムを貸して下さいませんか means that the lender is the listener, while A:私に消しゴムを借りさせて下さいませんか means that the lender is not necessarily the listener. Practically, you don't use A.

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We don't say the sentence A. I think the sentence B is a bit unnatural. It would be 消しゴムを貸してくれませんか or 消しゴムを貸して下さい.

The respect form of 借りる is お借りになる and the humble form of that is お借りする and 拝借する. So you can say 消しゴムをお借りしてもよろしいですか? and this is very polite.

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