SEFER CHOFETZ CHAIM
If one must inquire about a person, family, community, or school in order to make an important decision, but does not want others to know what he is contemplating, he may not engage people in casual conversation with the aim of obtaining pertinent derogatory or harmful information. Unaware that his speech is constructive, the speaker is guilty of speaking loshon hora, and the listener who drew him into conversation has caused him to sin.
Thus, when soliciting necessary information, one must make it clear to the other person that circumstances permit this and that his response, therefore will not constitute loshon hora.
A common practice in such situations is not only to refrain from divulging the purpose of the inquiry, but also to inquire about several people at once, so as to conceal the fact that it is a particular person about whom one is seeking information. This is absolutely forbidden. The desire to protect one’s privacy does not justify irrelevant negative information and causing others to speak loshon hora.
SEFER SHMIRAS HALOSHON
Love Your Fellow Jew
Fulfillment of the mitzvah to judge one’s fellow favorably and development of the quality of shmiras haloshon both hinge on the fulfillment of “You shall love your fellow as yourself” (Vayikra 19:18). If one truly loves his fellow Jew, surely he will not speak negatively of him; to the contrary, he will seek any possible merit for his actions, as he would for himself.
If one were to commit an act which appeared improper, and he were to learn that his action was being talked about by others, surely he would fervently hope that someone would speak up in his defense and explain that, for whatever reason, he was not at fault. This is exactly what one should do when someone else’s behavior comes under scrutiny.
Moreover, to love one’s fellow as oneself is to help him avoid situations which would result in his suffering shame or criticism.
Let us suppose that one finds himself for an extended period of time in a city whose customs are foreign to him. He would seek out a loyal friend in that city who could familiarize him with local customs and inform him privately when his behavior might evoke negative feelings among the city’s inhabitants. In this way, he would be forewarned of anything which could possibly cause him distress or embarrassment. One should act toward his fellow in exactly this manner. If one sees another Jew doing that which could ultimately lead to his distress or embarrassment, he is obligated to warn him of this.