I lent a friend money over a year ago and they have never mentioned it since. Every time we meet I am thinking about it. Do I ask, or do I let it go?

“When thou dost lend thy brother any thing, thou shalt not go into his house to fetch his pledge. Thou shalt stand abroad, and the man to whom thou dost lend shall bring out the pledge abroad unto thee.”

Israel's law permitted lending, but it regulated how a lender was allowed to behave when collecting. A creditor could not walk into the borrower's house and take the pledge himself; he had to stand outside and wait. The rule protects something easily lost in a money dispute: the dignity of the person who owes you. Being owed did not give you the right to diminish someone.

“And if ye lend to them of whom ye hope to receive, what thank have ye? for sinners also lend to sinners, to receive as much again. But love ye your enemies, and do good, and lend, hoping for nothing again; and your reward shall be great, and ye shall be the children of the Highest: for he is kind unto the unthankful and to the evil.”

Jesus is teaching a crowd about loving people who cannot balance the ledger. The lending he describes is deliberately uncomfortable, given without the calculation of return that made lending safe in the first place. He is not forbidding you from asking for repayment. He is naming what your heart should be prepared for, so the money never becomes the thing you value above the person.