Gift or Loan — Which is Preferable

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Question

A friend wants to borrow money from him, and he prefers to give him a gift. Which mitzvah is preferable: a gift or a loan?

Answer

A loan is preferable, so initially give it as a loan and then tell him that you are giving it as a gift. In this way, you gain both a loan and charity (if he is poor), and it is also easier to receive the money initially as a loan, making it more pleasant for him. When you forgive the debt, there is no longer any awkwardness associated with receiving a gift.

Source

Ketubot 67, Yoreh De'ah 253

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