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Re'eh"If there shall be a destitute person among you, any of your brethren in any of your cities, in the Land that Hashem, your G-d, gives you, you shall not harden your heart or close your hand against your destitute brother. Rather, you shall open your hand to him; you shall lend him his requirement, whatever is lacking to him" (Devarim 15:7-8).
Charity is not limited to a donation given to the collector at your door. Rashi explains: "Lend him" - If he does not want to accept a present, then give him money in the form of a loan. "His requirement" - however, you are not commanded to make him wealthy. "Whatever is lacking to him" - even a horse to ride upon and a servant to run before him. "Is lacking to him" - this refers to a wife.
HaRav Wolbe zt"l notes that there is no rule of thumb when it comes to a deficiency. He who would like to work on becoming a true benefactor must listen and look for what the recipient is really missing. The Torah states that we must wed the pauper a wife, and certainly she must be someone who is suitable for his personality and nature. So, too, we must address the rest of his material needs and deal with them in a manner that is fitting his stature and individuality.
Let us stop for a moment and try to picture the situation in which this formerly affluent man finds himself. He must move out of his mansion and into a humble abode. He has lost all his gold and silver utensils to his creditors. He can manage with all of this; yet, there is just one thing that he just can't handle: He has lost his fancy car and he must make his way around by foot or via public transportation. He leaves his house and returns home feeling humiliated. Such a person wouldn't have the audacity to ask that we supply him with a car; however, we ourselves should be able to understand that this is what he is truly lacking. Practically, those who are lacking food or require medical treatment might take precedence when deciding to whom we must donate our charity. Nevertheless, should we have the ability, one way or another, we would be obligated to provide him with the car that he is so sorely lacking.
If one would work on recognizing what this man is lacking, then instead of getting angry that he has the chutzpah to complain about his traveling when there are people crying for bread, we would look to lighten his burden. We will probably not be able to provide him with a "horse to ride upon and a servant to run before him", yet, if we truly understand him, we can comfort him, that with Hashem's help he will soon return to his former prominent standing.
Unfortunately, there are many different types of shortages. One person might need monetary help, while the second needs advice, needs to find a job, or needs medical or spiritual assistance. Some people speak about their problems, while others not only don't speak about them, but also don't know that they even exist. Before working on actually assisting others, we must first become aware of the matter in which they truly need assistance.
Let us take a minute to listen to another and try to understand what he is lacking. If he doesn't tell us straight out, then it might very well not be easy to discern what he is missing. However, recognizing where someone truly needs assistance is the first step in becoming a true helper of those in need.
Shema Yisrael Torah Network