You Shall Surely Reprove (but you don't need to be a jerk about it)

(17) You shall not hate your kinsfolk in your heart. Reprove your kinsman but incur no guilt because of him. (18) You shall not take vengeance or bear a grudge against your countrymen. Love your fellow as yourself: I am the LORD.

(6) If one man commit a sin against another man, the one sinned against shall not remain in silent hate against the sinner, as it is said of the wicked: "And Absalom spoke unto Amnon neither good nor bad; for Absalom hated Amnon" (Second Samuel. 13.22); but, on the contrary, it is obligatory upon him to make known to him and say unto him: "Why have you done to me thus and such, and wherefore have you sinned against me in that particular matter?"; for, it is said: "And thou shalt indeed rebuke thy neighbor" (Lev. 19.17). And, if the sinner did repent and begged to be forgiven by him, he must forgive him; and in doing so he should not be cruel, for it is said: "And Abraham prayed unto God" (Gen. 20.17).⁶For Abimelech, who sinned against him.

... He who rebukes his fellow, whether it be regarding a sin committed between man and man, or whether it be regarding matters between man and God, it is essential that the rebuke be administered only between them both; and he shall speak to him calmly, employing soft language, telling him that he does not speak of it to him, save for his own good, to bring him to a life in the world to come. If he receive it attentively from him, it is well; if not, he should rebuke him a second, even a third time. So is the constant duty of a man to continue to rebuke his fellow, even until the sinner strike him, and say unto him: "I will not listen". He in whose power it is to prevent sin and does not take the means to prevent it, he himself is ultimately overtaken by their sin, since it was possible for him to prevent them.⁷Shabbat, 54a; Ibid. 119b; Baba Mezi’a 31a. C. G.

(8) He who rebukes a friend, at the beginning, no hard words should be used against him to shame him, for it is said: "And thou shalt bear no sin upon him" (Lev. 19.17). Thus did the wise men say: "Understand it not by rebuking him thou mayest cause his countenance to change expression; for, it is said: 'And thou shalt bear no sin upon him'" (Ibid.; Arakin, 16b); herefrom we learn that it is forbidden to put an Israelite to shame, needless to say publicly. Although he who does put his fellow to shame is not flogged, it is a grievous sin. Even so did the wise men say: "He who publicly puts his fellow's countenance to shame has no share in the world to come" (Pirke Abot, 3.15). A man is, therefore obliged to guard himself against putting his fellow to shame publicly, regardless of whether he be young or old; not to call him by a name of which he feels ashamed, nor tell aught in his presence of which he is ashamed. Baba Mezi’a 59a; Yoma, 86b. C. G.

(10) The angry man cannot be very wise, for wrath causes reason to flee from the mind, so that he cannot answer as is proper, and he cannot rebuke as is proper, and all his words are not prompted by intelligence. The angry man bars from himself all corrections and rebukes, for no man feels free to reveal his errors and his shortcomings, inasmuch as every man fears him, — fears to tell him the things he does wrong, lest he be wrathful with him. And even if some person should rebuke him, the angry man will not receive correction because of his anger. In general then, an angry man does not acquire any good quality unless he first removes his anger from his heart. Just as the angry man does not accept rebuke from others, so is he not able to administer rebuke to others, for the Torah has said, "You shall surely rebuke your neighbor, and thus not bear sin because of his wrongful conduct" (Leviticus 19:17), which means that first you must rebuke him gently, and in private, and with soft speech, pleading with him that you are thinking only of his own good. And then, if you do this, sin will not accrue to you. But if you rebuke your companion right at the beginning, with an angry voice and with wrath, and you shame him, then you are sinning for your companion will not receive correction from you. For this is human nature, if a man comes to his companion with force then his companion will be stubborn and unyielding to him, and will not listen to him. Concerning this the wise man said in Koheleth, "The words of the wise are heard gently" (Eccl. 9:17), that is to say, the wise man speaks gently.

(21) Therefore, the Creator commanded us to rebuke those that fall short in the fulfillment of their duties, as written: "you shall surely rebuke your fellow" (Vayikra 19:17), and our sages taught: "until when is it one's duty to rebuke? Rav said: 'until he curses you', Shmuel said: 'until he assaults you' " (Erechin 16b), and it is said: "He that rebukes a man shall find more favor afterwards than he that flatters with the tongue" (Mishlei 28:23).

(14) For instance, the Torah commanded us: "you shall surely rebuke your fellow" (Vayikra 19:17). Very often a person attempts to rebuke sinners at a place or time when his words will not be heeded and he causes them to breach even further in their wickedness, to desecrate the Name of G-d, and to add transgression to their sin. In such cases, the only Chasidut is to keep silent. Thus, our sages, of blessed memory, said: "just like it is a mitzva to say what will be heeded, so too it is a mitzva to not say what will not be heeded" (Yevamot 65b).

(12) Even when it becomes necessary to rebuke someone we have been warned not to rebuke with cruelty, as it is written: "You shall surely rebuke your neighbor but not bear sin because of him" (Lev. 19:17), which means "Do not rebuke him strongly and with cruelty to shame him and thus be guilty of sinning against him."

(24) And one should be very careful not to shame any man for the Sages said: "He who whitens (shames) the face of another in public has no portion in the world to come" (Baba Mezià 59a). To whiten another's face is like murder, for the red departs and the white comes (thus one is spilling the blood of the shamed one within him) (Ibid., 58b). And the Sage said further: The pain of shame is worse than death. A person should allow himself to be burnt alive and not shame his fellow in public. And they learned this from Tamar who, even though they brought her forth to be burned, did not want to shame Judah (Berakoth 43b). And even when you are required to rebuke another the Torah says: "You shall surely rebuke your neighbor and not bear sin because of him" (Lev. 19:17). How shall you rebuke? At first, secretly and gently. However if you rebuke him at the beginning in public and shame him, then you have sinned because of this, (Arakin 16b). And this is all the more true where one shames another where no rebuke is called for.