Question: If one wronged one’s friend, must one appease the wronged party on his own or may one send an agent to appease him on his behalf?
Answer: From the words of the Rambam (Chapter 2 of Hilchot Teshuva) we have learned that one who has sinned against his friend, such as by insulting him and the like, must go on his own and appease the individual who he has wronged and request his forgiveness. Only if the friend refuses to forgive him should the sinner send others to ask for forgiveness on his behalf, as the Rambam explains in detail.
Based on this, Hagaon Harav Yaakov ben Chaviv infers (in his Ein Yaakov, end of Masechet Yoma) that this which is customary that when one sins against his friend and verbally offends him, a third party enters the scene and tries to broker a truce between them and, after he has spoken to the wronged party, the sinner then goes on his own to the wronged individual and asks forgiveness, this is an incorrect custom; rather, the insulting party must confront the wronged party directly to begin with and request his forgiveness until he says the words “I forgive you.”
Indeed, many great Poskim, including the Kenesset Ha’Gedolah and Bayit Chadash, quote the opinion of Rabbeinu Yaakov ben Chaviv as Halacha.
Nevertheless, Hagaon Rabbeinu Chizkiya de Silwa writes in his Peri Chadash (Chapter 606) that the opinion of Rabbeinu Yaakov ben Chaviv is not necessarily correct. Similarly, Hagaon Harav Chaim Palagi (in his Sefer Le’Chaim Birushalayim) quotes the words of the Yefeh Mareh who disagrees with the opinion of Rabbeinu Yaakov ben Chaviv and writes that one should always carry out the means which is most constructive towards reaching the goal, i.e. for the wronged party to be appeased. We are not concerned about the method through which the wronged party will be appeased. He proceeds to bring a source for this idea from the Midrash which states that Aharon Ha’Kohen would first appease the wronged party in order to increase peace amongst the Jewish nation and only then would the two individuals meet and reconcile. Maran zt”l (in his Responsa Yechave Da’at, Volume 5, Chapter 44 and Chazon Ovadia-Yamim Nora’im, page 240) likewise questions the ruling of Rabbeinu Yaakov ben Chaviv from another Midrash which states that the brothers of Yosef sent the sons of Bilhah to appease Yosef for them having sold him and only later did the brothers come before him themselves.
Although these Midrashim alone are not quite sufficient to disprove the opinion of Rabbeinu Yaakov ben Chaviv, Maran zt”l writes that halachically speaking, if one sins against his friend, one should appease the wronged party himself and not send an agent to do so on his behalf. Nevertheless, this depends on the specific circumstance, for if it is known that the individual who was wronged is easily appeased and the sinner believes that he will be more easily appeased if he sends a respectable and close friend of his to assuage him first, one should do so. Afterwards, the sinner should come forward himself and second the messenger’s words by asking for forgiveness.
Pirkei De’Rabbi Eliezer (Chapter 46) states that the Satan prosecutes the Jewish nation every day. However, on the day of Yom Kippur, the Satan himself comes to their defense and tells Hashem, “You have a nation that is similar to the Heavenly angels: Just as the Heavenly angels are clean, so is the Jewish nation. Just as there is peace among the Heavenly angels, the same holds true for the Jewish nation.” Hashem listens to the Satan’s testimony and then pardons the Jewish nation.