187. Rebuke

29:15 If one sees that a friend has sinned or is pursuing an improper path, he is obligated to try to return him to the proper way as per Leviticus 19:17, “You shall surely rebuke your friend.” A person should only be rebuked in private and in a calm, gentle tone. (If he is sinning publicly, he must be rebuked immediately in order to prevent a chillul Hashem – Mishnah Brurah 608:10.) We must explain that we are doing this because we are concerned for his spiritual well-being. If one has the opportunity to prevent another’s misdeeds and fails to do so because he did not speak up, he is considered partially responsible for the subsequent sins.

29:16 The above only applies when a person believes that his friend might listen to him. If one knows that he’s going to be ignored, one should not rebuke his friend. (This is when the prohibition is not explicit in the Torah. If it is explicit in the Torah, one must rebuke another even if it is likely that the other may not listen - Rema 608:2.) Rabbi Ilai said in the name of Rabbi Eliezer that it’s a mitzvah to say things that will be heeded and it’s a mitzvah not to say things that won’t be heeded (Talmud Yevamos 65b). Rabbi Abba says this is an obligation based on Proverbs 9:8, “Do not rebuke a jester because he will just despise you for it; rebuke a wise man and he will love you for it.”