DEUT782 He who gives charity to the poor with a mean expression loses his merit, and he transgresses (this verse): "And let your heart not be evil when you give to him," even if he gives much. It is better to give a perutah [a small coin] with a pleasant expression. The ideal is to give correctly to a deserving poor man, with a pleasant expression. It is better to give before one is asked, and to give in secret, as it is written (Mishlei 21:14): "He who gives in secret suppresses wrath." Some men were in the practice of tying money in a piece of cloth and casting it behind them for the poor (Kesubos 67b), so that the giver did not know to whom he had given and the recipient from whom he had taken, thus sparing the poor embarrassment. In summary: Whatever can be done in secret, so that the poor man does not know the giver and the giver does not know the recipient, should be done. And when a man gives charity, he should accompany it with lovingkindness, such as buying with his money something that the poor man needs in order to spare him the bother of buying it himself. Or, finding that a poor man's needs can be cheaply acquired at a certain time, but that he is lacking in means, you should supply him with the necessary funds, making sure to do so at that particular time, thus showing lovingkindness. About this the prophet has said (Hoshea 10:12): "Sow for yourselves with charity; harvest with lovingkindness." That is, the reward is commensurate with the lovingkindness (Sukkah 49b).