Is It Too Late to Apologiiiize?

Maimonides’ Four Steps to Apologizing

The most famous laws about apology come to us from the 12th century rabbi, philosopher, and physician Maimonides (1135-1204, Spain), or Rambam, one of the greatest Torah scholars of the Middle Ages. Maimonides wrote codes of law for the Jewish community, clarifying common Jewish practice and accepted standards of observance.

According to Maimonides, four of the most important steps of teshuvah (repentance) are the following:

  1. Verbally confess your mistake and ask for forgiveness (Mishneh Torah 1:1).
  2. Express sincere remorse, resolving not to make the same mistake again (Mishneh Torah 2:2).
  3. Do everything in your power to “right the wrong,” to appease the person who has been hurt by your actions (Mishneh Torah 2:9).
  4. Act differently if the same situation happens again (Mishneh Torah 2:1).

The fourth concept originates in the Talmud:

היכי דמי בעל תשובה אמר רב יהודה כגון שבאת לידו דבר עבירה פעם ראשונה ושניה וניצל הימנה מחוי

§ With regard to repentance, the Gemara asks: What are the circumstances that demonstrate that one has completely repented? Rav Yehuda said: For example, the prohibited matter came to his hand a first time and a second time, and he was saved from it, thereby proving that he has completely repented.

We're also given clear guidance on the importance of our intention with an apology--Judaism teaches that in order for an apology to really "count" we have to genuinely MEAN it.

(ד) ב,ד [ג] כָּל הַמִּתְוַדֶּה בִּדְבָרִים, וְלֹא גָמַר בְּלִבּוֹ לַעֲזֹב--הֲרֵי זֶה דּוֹמֶה לְטוֹבֵל, וְשֶׁרֶץ בְּיָדוֹ, שְׁאֵין הַטְּבִילָה מוֹעֶלֶת, עַד שֶׁיַּשְׁלִיךְ הַשֶּׁרֶץ; וְכֵן הוּא אוֹמֵר "וּמוֹדֶה וְעֹזֵב, יְרֻחָם" (משלי כח,יג). וְצָרִיךְ לִפְרֹט אֶת הַחֵטְא, שֶׁנֶּאֱמָר "אָנָּא, חָטָא הָעָם הַזֶּה חֲטָאָה גְדֹלָה, וַיַּעֲשׂוּ לָהֶם, אֱלֹהֵי זָהָב" (שמות לב,לא).

(4) Anyone who confesses verbally and does not commit in his heart to abandon [sin], this is like a person who immerses [in a purity pool] while holding an unclean creature in his hand, so that the bath is not effective until he sends away the unclean creature, and so it says, One who admits and abandons is given mercy (Proverbs 28:13). And he must specify the sin, as it says, This nation has sinned a great sin and made a golden god for themselves (Exodus 32:31).

Along with guidance on how to ask for forgiveness, Maimonides also teaches that the recipient of an apology should be open to offering forgiveness and receiving the apology.

...וּבְשָׁעָה שֶׁמְּבַקֵּשׁ מִמֶּנּוּ הַחוֹטֵא לִמְחל מוֹחֵל בְּלֵב שָׁלֵם וּבְנֶפֶשׁ חֲפֵצָה. וַאֲפִלּוּ הֵצֵר לוֹ וְחָטָא לוֹ הַרְבֵּה לֹא יִקֹּם וְלֹא יִטֹּר...

...when a sinner implores him for pardon, he should grant him pardon wholeheartedly and soulfully. Even if one persecuted him and sinned against him exceedingly he should not be vengeful and grudge-bearing...

ר' זירא כי הוה ליה מילתא בהדי איניש הוה חליף ותני לקמיה וממציא ליה כי היכי דניתי וניפוק ליה מדעתיה
It is related that when Rabbi Zeira had a complaint against a person who insulted him, he would pace back and forth before him and present himself, so that the person could come and appease him. Rabbi Zeira made himself available so that it would be easy for the other person to apologize to him.
אָסוּר לָאָדָם לִהְיוֹת אַכְזָרִי וְלֹא יִתְפַּיֵּס אֶלָּא יְהֵא נוֹחַ לִרְצוֹת וְקָשֶׁה לִכְעֹס וּבְשָׁעָה שֶׁמְּבַקֵּשׁ מִמֶּנּוּ הַחוֹטֵא לִמְחל מוֹחֵל בְּלֵב שָׁלֵם וּבְנֶפֶשׁ חֲפֵצָה. וַאֲפִלּוּ הֵצֵר לוֹ וְחָטָא לוֹ הַרְבֵּה לֹא יִקֹּם וְלֹא יִטֹּר. וְזֶהוּ דַּרְכָּם שֶׁל זֶרַע יִשְׂרָאֵל וְלִבָּם הַנָּכוֹן. אֲבָל הָעוֹבְדֵי כּוֹכָבִים עַרְלֵי לֵב אֵינָן כֵּן אֶלָּא (וְעֶבְרָתָן) [וְעֶבְרָתוֹ] שְׁמָרָה נֶצַח. וְכֵן הוּא אוֹמֵר עַל הַגִּבְעוֹנִים לְפִי שֶׁלֹּא מָחֲלוּ וְלֹא נִתְפַּיְּסוּ וְהַגִּבְעֹנִים לֹא מִבְּנֵי יִשְׂרָאֵל הֵמָּה:

One must not show himself cruel by not accepting an apology; he should be easily pacified, and provoked with difficulty. When an offender asks his forgiveness, he should forgive wholeheartedly and with a willing spirit. Even if he has caused him much trouble wrongfully, he must not avenge himself, he must not bear a grudge. This is the way of the stock of Israel and their upright hearts.— — Concerning the Gibeonites who refused to forgive and be appeased, it is written: "The Gibeonites did not belong to the people of Israel" (II Samuel 21:2).