Asking Mechila - Yechaveh Daat 5:44

Rabbi Ovadiah Yosef was asked if one needs to ask forgiveness from others in person, or if it could be done via messenger or letter (and I would update that to include email and Facebook posts).

Rav Yosef begins his reply by discussing the general severity of the requirement to ask forgiveness from others before Yom Kippur. There is a debate in the Gemara and through the Rishonim and Acharonim whether repenting before God and repenting before our fellow man are two separate requirements that can exist separately, or whether failure to do one holds back our performance of the other. In other words, if one fails to gain forgiveness from others, there is a view that his sins before God are not forgiven either. The general reason given for this stricter approach is that if one does not seek forgiveness from his friend, then he is rejecting that mitzva of the Torah, and thus his repentance before God loses some of its meaning.

[Mori V'Rabi Rav Aharon Lichtenstein noted in a teshuva lecture in 1997 that this idea is based on the last mishna in Yoma, where Rabi Akiva notes that we are fortunate to become purified before Hashem, based on the verse מקוה ישראל ה' - Rav Lichtenstein pointed out that there is something frightening in this statement. Since one who enters a mikveh holding a שרץ is not purified, so too one who repents before God while still holding onto his sins vis-a-vis others also cannot become fully purified and forgiven.]

After concluding his lengthy introduction about the necessity of seeking out others to ask them for forgiveness, Rav Yosef rules that it is preferable to ask someone for forgiveness in person. While it is true that Yosef's brothers sent a conciliatory mission to him after Yaakov's death and Aharon HaKohein would serve as a go-between when making peace between adversaries, nevertheless the preferred approach is that one confront his friend personally and ask for forgiveness. In certain situations, depending on either the stature of the individuals involved and/or the severity of the offense, it may be prudent to first send someone else to lay the groundwork for the eventual rapprochement.

Rav Yosef concludes by noting that it is important for children to ask forgiveness from their parents, as people constantly stumble in their performance of the mitzva to respect their parents. Similarly, husbands and wives must ask forgiveness from one another, and students must ask forgiveness from their teachers.

Wishing everyone a גמר חתימה טובה.

Teshuva for serious sins - Igrot Moshe Orach Chaim 4:115-118

In this suite of teshuvot from the mid-1970's, Rav Moshe Feinstein responds to anonymous questioners who were seeking to do teshuva for a variety of sins of a sexual nature, including homosexual acts, masturbation, an office affair (asked by the woman), and pre-marital sex (also asked by the woman).

There are several notable points about these teshuvot:

1) Rav Moshe's extreme sensitivity towards those asking the question, as he takes the basic stance that despite the severity of their sins, the fact that they are asking the question about doing teshuva indicates that they are clearly regretful of their actions and are thus on the right path.

2) Rav Moshe prescribes several actions for the penitents, including learning Torah, reciting Tehillim, and private confessions, based on the logic that actions are stronger than mere thoughts and that taking various practices upon oneself will serve as an inoculation against the thoughts that led to the various actions.

An interesting issue arose with the last case, where the woman who had had pre-marital relations was getting married and did not want her past misdeeds to be known to anyone other than her future husband. Rav Moshe permitted her to have the ketubah read the same as the ketubah of a virgin, based on the fact that since her husband knew the truth about her past and nevertheless accepted upon himself the responsibilities of a full ketubah, there would thus be no issue of the ketubah being false and there would be no need to even inform the mesader kiddushin of this fact.