Requesting Forgiveness via Letter or Messenger
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Question
A person who has offended a friend with words but is embarrassed to go and ask for forgiveness, can he send words of reconciliation and apology in a letter or through a messenger?
Answer
Since a person who goes himself to ask for forgiveness has greater repentance than if he sends a messenger, it is advisable to make an effort to ask for forgiveness personally. However, if it is difficult for him, he can send a messenger to reconcile with his friend or send him a letter. But sending a letter without the sender's details is of no benefit and does not help in the request for forgiveness at all.
Source
Mishnah Berurah (Siman 606, Se'if Katan 2). It is also mentioned in the name of the Chazon Ish that the main reconciliation with a friend is the humility when one humbles himself to ask for forgiveness, and it is a form of counterbalance for the reconciler, and therefore it is worth making an effort to ask for forgiveness personally.
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