The Torah commands in Parashat Kedoshim (Vayikra 19:17), “Hochi’ah Tochi’ah Et Amitecha” – “You shall surely reprimand your fellow.” This command establishes the obligation to approach somebody whom we observe committing a misdeed – whether an interpersonal offense, or a sin against G-d – in an attempt to correct his behavior. The Torah issues this command with the double expression “Hochi’ah Tochi’ah,” which the Sages understood as indicating that if our initial attempt to correct the individual’s behavior does not succeed, we must try again. Even if we need to approach the person and speak to him one hundred times in an effort to lead him to change, we are obliged to do so.
The verse continues, “Ve’lo Tisa Alav Het” (“You shall not bear iniquity on his account”), which the Sages interpreted to mean that one is not permitted to embarrass his fellow in the course of reprimanding him. The words of rebuke must be spoken lovingly, calmly and respectfully, and not in an angry outburst which will cause the sinner to feel embarrassed.
A person must repeatedly reprimand his fellow, if necessary, until he fears that the sinner will respond with physical violence if he persists. At that point, there is no longer an obligation to reprimand the sinner.
The Sefer Ha’hinuch writes that before speaking words of rebuke in fulfillment of this Misva, one should offer a prayer to G-d, asking that his efforts should be successful. Teshuba (repentance) is possible only with G-d’s assistance, and so one should first pray that his efforts to inspire his fellow to repent will succeed, and trust in His help. The Sefer Ha’hinuch also emphasizes that one is worthy of great reward if he succeeds in leading a sinner back to the path of proper behavior. Conversely, a person who is in a position to correct his fellow’s behavior but fails to do so bears a degree of responsibility for his fellow’s continued wrongdoing.
This obligation applies in all times, in all places, and to both men and women. One who fails to reprimand a sinner whom he could have led to repentance transgresses this affirmative command, and, as mentioned, bears guilt for the sinner’s misconduct henceforth.
The later scholars addressed the question of whether one transgresses this Misva if he neglects to reprimand a sinner but the sinner then repents on his own, without this individual’s intervention. Rav Yehonatan Eibshutz (1690-1764), in Ya’arot Debash (11), maintained that the individual is not considered to have neglected this Misva in such a case. He explains that the obligation to reprimand a sinner is rooted in the principle of “Kol Yisrael Arebim Zeh La’zeh” – that we are all responsible for each other’s religious observance. If a person committed a sin, then those who could have prevented it bear a degree of accountability for that misdeed. Hence, Rav Eibshutz writes, if the person repented, then those who failed to reprimand him have nothing for which to be held responsible, since the sinner repented and did not continue acting wrongly. As such, they have not transgressed this Misva. Others, however, disagree, claiming that once the Torah obligates a person to try to correct his fellow’s behavior, he is in violation of this command once he fails to do, even if his fellow repents on his own.
In conclusion, it is worth noting the significance of the aforementioned Halacha requiring one to reprimand his fellow even one hundred times if necessary. This Halacha demonstrates that we do not give up on our fellow Jew, even after numerous unsuccessful attempts to influence him to improve. We are to firmly believe in every person’s capacity to repent and improve his behavior, and never assume that a sinner will always continue his current improper behavior patterns.