The Art of Rebuke
(יז) לֹֽא־תִשְׂנָ֥א אֶת־אָחִ֖יךָ בִּלְבָבֶ֑ךָ הוֹכֵ֤חַ תּוֹכִ֙יחַ֙ אֶת־עֲמִיתֶ֔ךָ וְלֹא־תִשָּׂ֥א עָלָ֖יו חֵֽטְא׃
(17) You shall not hate your kinsfolk in your heart. Reprove your kinsman but incur no guilt because of him.

כְּשֶׁיֶּחְטָא אִישׁ לְאִישׁ לֹא יִשְׂטְמֶנּוּ וְיִשְׁתֹּק ... אֶלָּא מִצְוָה עָלָיו לְהוֹדִיעוֹ וְלוֹמַר לוֹ לָמָּה עָשִׂיתָ לִי כָּךְ וְכָךְ וְלָמָּה חָטָאתָ לִי בְּדָבָר פְּלוֹנִי. שֶׁנֶּאֱמַר (ויקרא יט יז) "הוֹכֵחַ תּוֹכִיחַ אֶת עֲמִיתֶךָ". וְאִם חָזַר וּבִקֵּשׁ מִמֶּנּוּ לִמְחֹל לוֹ צָרִיךְ לִמְחֹל. וְלֹא יְהֵא הַמּוֹחֵל אַכְזָרִי ...

If one man commit a sin against another man, the one sinned against shall not remain in silent hate against the sinner,... 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 ...

רַב וְרַבִּי חֲנִינָא וְרַבִּי יוֹחָנָן וְרַב חֲבִיבָא מַתְנוּ: בְּכוּלֵּיהּ דְּסֵדֶר מוֹעֵד כָּל כִּי הַאי זוּגָא חַלּוֹפֵי רַבִּי יוֹחָנָן וּמְעַיֵּיל רַבִּי יוֹנָתָן. כׇּל מִי שֶׁאֶפְשָׁר לִמְחוֹת לְאַנְשֵׁי בֵיתוֹ וְלֹא מִיחָה — נִתְפָּס עַל אַנְשֵׁי בֵיתוֹ. בְּאַנְשֵׁי עִירוֹ — נִתְפָּס עַל אַנְשֵׁי עִירוֹ. בְּכָל הָעוֹלָם כּוּלּוֹ — נִתְפָּס עַל כָּל הָעוֹלָם כּוּלּוֹ.

Throughout the order of Moed, wherever this pair of Sages is mentioned, exchange Rabbi Yoḥanan and insert Rabbi Yonatan in his place. In any event, they said: Anyone who had the capability to effectively protest the sinful conduct of the members of his household and did not protest, he himself is apprehended for the sins of the members of his household and punished. If he is in a position to protest the sinful conduct of the people of his town, and he fails to do so, he is apprehended for the sins of the people of his town. If he is in a position to protest the sinful conduct of the whole world, and he fails to do so, he is apprehended for the sins of the whole world.

[ח]... ומנין שאם הוכחתו ארבעה וחמשה פעמים חזור והוכיח? תלמוד לומר "הוכח תוכיח". יכול אפילו אתה מוכיחו ופניו משתנות? תלמוד לומר "ולא תשא עליו חטא".

8)... "whence is it derived that if he reproved him four or five times (and he did not take heed), he should keep on doing so? From "Reprove shall you reprove." I might think that he must do so even if his face changes color (in shame); it is, therefore, written "but do not bear sin because of him."

הָרוֹאֶה חֲבֵרוֹ שֶׁחָטָא אוֹ שֶׁהָלַךְ בְּדֶרֶךְ לֹא טוֹבָה מִצְוָה לְהַחֲזִירוֹ לַמּוּטָב וּלְהוֹדִיעוֹ שֶׁהוּא חוֹטֵא עַל עַצְמוֹ בְּמַעֲשָׂיו הָרָעִים שֶׁנֶּאֱמַר (ויקרא יט יז) "הוֹכֵחַ תּוֹכִיחַ אֶת עֲמִיתֶךָ". הַמּוֹכִיחַ אֶת חֲבֵרוֹ. בֵּין בִּדְבָרִים שֶׁבֵּינוֹ לְבֵינוֹ. בֵּין בִּדְבָרִים שֶׁבֵּינוֹ לְבֵין הַמָּקוֹם. צָרִיךְ לְהוֹכִיחוֹ בֵּינוֹ לְבֵין עַצְמוֹ. וִידַבֵּר לוֹ בְּנַחַת וּבְלָשׁוֹן רַכָּה וְיוֹדִיעוֹ שֶׁאֵינוֹ אוֹמֵר לוֹ אֶלָּא לְטוֹבָתוֹ לַהֲבִיאוֹ לְחַיֵּי הָעוֹלָם הַבָּא. אִם קִבֵּל מִמֶּנּוּ מוּטָב וְאִם לָאו יוֹכִיחֶנּוּ פַּעַם שְׁנִיָּה וּשְׁלִישִׁית. וְכֵן תָּמִיד חַיָּב אָדָם לְהוֹכִיחוֹ עַד שֶׁיַּכֵּהוּ הַחוֹטֵא וְיֹאמַר לוֹ אֵינִי שׁוֹמֵעַ. וְכָל שֶׁאֶפְשָׁר בְּיָדוֹ לִמְחוֹת וְאֵינוֹ מוֹחֶה הוּא נִתְפָּשׂ בַּעֲוֹן אֵלּוּ כֵּיוָן שֶׁאֶפְשָׁר לוֹ לִמְחוֹת בָּהֶם:

He who beholds his fellow stooping to sin or following an unrighteous path, is obliged to return him toward the good, and to let him know that he is actually sinning against himself in pursuing wicked deeds for, it is said: "And thou shalt indeed rebuke thy neighbor" (Lev. 19.17). 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.

הַמּוֹכִיחַ אֶת חֲבֵרוֹ תְּחִלָּה לֹא יְדַבֵּר לוֹ קָשׁוֹת עַד שֶׁיַּכְלִימֶנּוּ שֶׁנֶּאֱמַר (ויקרא יט יז) "וְלֹא תִשָּׂא עָלָיו חֵטְא". כָּךְ אָמְרוּ חֲכָמִים יָכוֹל אַתָּה מוֹכִיחוֹ וּפָנָיו מִשְׁתַּנּוֹת תַּלְמוּד לוֹמַר וְלֹא תִשָּׂא עָלָיו חֵטְא. מִכָּאן שֶׁאָסוּר לָאָדָם לְהַכְלִים אֶת יִשְׂרָאֵל וְכָל שֶׁכֵּן בָּרַבִּים. אַף עַל פִּי שֶׁהַמַּכְלִים אֶת חֲבֵרוֹ אֵינוֹ לוֹקֶה עָלָיו עָוֹן גָּדוֹל הוּא. כָּךְ אָמְרוּ חֲכָמִים (גמרא סנהדרין קז א) "הַמַּלְבִּין פְּנֵי חֲבֵרוֹ בָּרַבִּים אֵין לוֹ חֵלֶק לָעוֹלָם הַבָּא". לְפִיכָךְ צָרִיךְ אָדָם לְהִזָּהֵר שֶׁלֹּא לְבַיֵּשׁ חֲבֵרוֹ בָּרַבִּים בֵּין קָטָן בֵּין גָּדוֹל. וְלֹא יִקְרָא לוֹ בְּשֵׁם שֶׁהוּא בּוֹשׁ מִמֶּנּוּ. וְלֹא יְסַפֵּר לְפָנָיו דָּבָר שֶׁהוּא בּוֹשׁ מִמֶּנּוּ. בַּמֶּה דְּבָרִים אֲמוּרִים בִּדְבָרִים שֶׁבֵּין אָדָם לַחֲבֵרוֹ. אֲבָל בְּדִבְרֵי שָׁמַיִם אִם לֹא חָזַר בּוֹ בַּסֵּתֶר מַכְלִימִין אוֹתוֹ בָּרַבִּים וּמְפַרְסְמִים חֶטְאוֹ וּמְחָרְפִים אוֹתוֹ בְּפָנָיו וּמְבַזִּין וּמְקַלְּלִין אוֹתוֹ עַד שֶׁיַּחֲזֹר לַמּוּטָב כְּמוֹ שֶׁעָשׂוּ כָּל הַנְּבִיאִים בְּיִשְׂרָאֵל:
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. However, all these refer to matters touching the relationship between man and man; but if it concern heavenly matters, if the sinner does not repent after being rebuked privately, he should be shamed publicly, and his sin should be proclaimed, and harsh words should be used in his presence, and he should be shamed and cursed till he repent and take up the good path, even as all of the prophets in Israel did with the wicked.

תניא א"ר טרפון (תמיהני) אני אם יש בדור הזה שמקבל תוכחה אם אמר לו טול קיסם מבין עיניך אמר לו טול קורה מבין עיניך אמר רבי אלעזר בן עזריה תמיהני אם יש בדור הזה שיודע להוכיח

It is taught in a baraita that Rabbi Tarfon says: I would be surprised if there is anyone in this generation who can receive rebuke. Why? Because if the one rebuking says to him: Remove the splinter from between your eyes, i.e., rid yourself of a minor infraction, the other says to him: Remove the beam from between your eyes, i.e., you have committed far more severe sins. Rabbi Elazar ben Azaria says: I would be surprised if there is anyone in this generation who knows how to rebuke correctly, without embarrassing the person he is rebuking.

(ח) אַל־תּ֣וֹכַח לֵ֭ץ פֶּן־יִשְׂנָאֶ֑ךָּ הוֹכַ֥ח לְ֝חָכָ֗ם וְיֶאֱהָבֶֽךָּ׃

(8) Do not rebuke a scoffer, for he will hate you; Reprove a wise man, and he will love you.