Halachos of Appeasing Another Jew part 2
By Rabbi Yochanan Eskenazi
If one upset another person, even if it was only with words, he is required to make amends (Shulchan Aruch 606:1). This includes even if someone is unjustly upset at you (Koveitz Halachos [Piskei Harav Shmuel Kamenetsky, shlit"a] 25:16). If one is unsure whether he harmed someone else, he must ask for forgiveness (Aruch Hashulchan 606:4). Therefore it is vital that spouses and family members should ask for forgiveness from one another since it is extremely likely that over the course of the year they did something to warrant an apology (Koveitz Halachos 25:15).
If someone wronged another person, even if he is certain that he was forgiven, it is nevertheless proper to ask for forgiveness, since asking for forgiveness builds humility, which is part of the teshuva process (Koveitz Halachos 25:5).
If one asks a group of people for forgiveness, and he knows that he wronged an individual in that group, he has not fulfilled his obligation of asking forgiveness (Mishneh Berurah 606:3).
If someone truly feels bad for what he did, yet he is too embarrassed to ask for forgiveness, if he knows the person who he harmed says Tefillas Zakah one may b'dieved rely on this [and not actually ask him to forgive him] (Koveitz Halachos 25:5 & ftnt. 10 quoting Harav Yosef Shalom Eliyashuv, zt"l).
It is better to seek forgiveness in person. This includes asking for forgiveness via telephone. One may not write a letter because one does not feel so embarrassed (Koveitz Halachos 25:4). If one feels that the person he wronged will be more receptive to an intermediary he does not need to ask himself (Mishneh Berurah 606:2).
If one cannot reach the person he harmed before Yom Kippur, he should commit himself to seek forgiveness as soon as he is able to (The Power of Teshuva pg. 244 quoting Yapheh L'laiv 6:2). If the person who was wronged has died, one should ask forgiveness at the grave in the presence of ten people (Shulchan Aruch 609:2).
When appeasing another person, one needs to specify the aveira that he did, unless it would cause that person to become upset (Magen Avraham 606:1).
If one tried to appease his friend, yet the friend did not want to forgive him, one is obligated to ask for forgiveness three times. If one wronged his Rebbe, he must continue to appease him until he is granted forgiveness (Shulchan Aruch 606:1). Each new time, he should try to appease in a different way than was tried before (Magen Avraham 606:1). Additionally, the second and third time one comes to ask forgiveness from someone else, he should be accompanied by two other people (Rambam Hilchos Teshuva 2:9 & Shaarei Teshuva 4:19). One can even bring minors (Koveitz Halachos 25:3). If one feels that the person will forgive him without him bringing other people, he may go alone. This may be the reason why nowadays generally people do not bring other people (Koveitz Halachos 25:ftnt. 1).
There is a machlokes if one did ask for forgiveness, and the person said he forgives him, but in his heart he does not really mean it, has the person fulfilled his mitzvah of appeasing his friend (The Monthly Halachah Discussion [Rabbi D. Neustadt,shlit"a] pg. 323).
The Rama [606:1] writes, if one comes to request forgiveness from you, do not be cruel and forgive them. The Mishneh Berurah [ibid: 8] explains because in the Heavenly court you will be treated measure for measure.
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