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Matthew 5:42 Give to him that asketh thee. This is the general rule. It is better to give sometimes to an undeserving person, than to turn away one really necessitous. It is good to be in the habit of giving. At the same time, the rule must be interpreted so as to be consistent with our duty to our families, (#1Ti 5:8) and with other objects of justice and charity. It is seldom, perhaps never, good to give to a man that is able to work, #2Th 3:10. To give to such is to encourage laziness, and to support the idle at the expense of the industrious. If such a man is indeed hungry, feed him; if he wants anything farther, give him employment. If a widow, an orphan, a man of misfortune, or a man infirm, lame, or sick, is at your door, never send them away empty. See #Heb 13:2 Mt 25:35-45. So of a poor and needy friend that wishes to borrow. We are not to turn away, or deny him. This deserves, however, some limitation. It must be done in consistency with other duties. To lend to every worthless man, would be to throw away our property, encourage laziness and crime, and ruin our families. It should be done consistently, and of this every man is to be the judge. Perhaps our Saviour meant to teach that where there was a deserving friend or brother in want, we should lend to him, without usury, and without standing much about the security. - Barnes Notes

Matthew 5:42 Give to him that asketh thee, and from him that would borrow of thee turn not thou away.
Jesus here turns from the negative to the positive side of life. Our conduct, instead of being selfish and revengeful, should be generous and liberal. A benevolent disposition casts out revenge as light does darkness. No lending was provided for by the law of Moses except for benevolent purposes, for no interest was allowed, and all debts were canceled every seventh year. The giving and lending referred to, then, are limited to cases of real want, and the amount given or loaned is to be regulated accordingly. Giving or lending to the encouragement of vice or indolence cannot, of course, be here included. Good actions are marred if they bear evil fruit.          

- The Fourfold Gospel