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As customers, do widows deserve special treatment ?
Q. If I have a customer who is a widow, should I give her a discount? If she's late paying, am I allowed to use normal collection actions?
A. In many places, the Torah admonishes us to display special consideration towards widows. We will be able to answer your question if we examine the nature of these varying admonitions.
The first consideration is relevant to your question if the widow is poor. While there is no particular commandment to give a discount to poor people or to refrain from collecting from them, we have discussed many times in the past that the ideal way of helping the needy is through normal market transactions. If you are in a position to give charity to the poor, then an excellent way of doing so is by giving service to them at specially low prices or at unusually favorable terms of credit. This would apply particularly to a widow.
The second consideration is relevant irrespective of the widow's financial situation. We need to relate to everybody in a thoughtful and considerate way, but this is particularly important with someone who is emotionally vulnerable.
Between these two extremes of economic and emotional interaction, there is an intermediate kind that we have often discussed: the human dimension of our market activities. This aspect is related to in the Torah in a third mandate which is a kind of hybrid of the other two. The Torah warns us not to demand a pawn (collateral) from a widow before the loan is due. "Don't distort the judgment of a stranger or an orphan, and don't repossess the garment of a widow" (Deuteronomy 24:17). The Talmud concludes that this commandment, despite its economic nature, applies even to a wealthy widow. The explanation is that this kind of demand can be demeaning or distressing beyond its economic impact.
This commandment is relevant for your situation. A person is always allowed to collect money for services rendered, but even legitimate collection actions sometimes have a way of declining into very adversarial procedures that neither side is necessarily particularly proud of afterwards. If a widow is involved, we should be especially careful to make sure all collection actions or legal actions are carried out in a businesslike fashion.
Some authorities have written that this commandment applies equally to divorced women. (Sema, Choshen Mishpat 97:22.) In general, we should learn from the Torah's attitude towards widows that we should display special consideration towards anyone who is financially or emotionally vulnerable.