Unpacking the Iggerot: Responses to Repentance

Moshe Kurtz Tradition Online | August 1, 2024

Read more about “Unpacking the Iggerot” and see the archive of all past columns.

Iggerot Moshe, Orah Hayyim, vol. 4, #114

Summarizing the Iggerot

For people with standard work schedules, the fast days populating the Jewish calendar can occur at very inconvenient times, forcing individuals to decide between a productive work day or a successful fast. After the many Jewish holidays, an observant employee might find that they are running low on vacation days and are left between a rock and a hard place. Rabbi Moshe Feinstein was asked whether someone may take out a “loan” and give God an I.O.U. to make up a minor fast on a different day when he could more easily manage the deficit of daily nutrition.

R. Feinstein approached this query by distinguishing between a personal fast that one accepts by his own prerogative versus a calendric fast day such as the 10th of Tevet or the 17th of Tammuz:

It is obvious that to take out a loan on the fast and repay it on another day is impossible according to all opinions. This [is true] even according to those who posit that if one takes an oath [to voluntarily fast] on one day they may “borrow and repay it.” For this only applies to an individual’s fast and not for a communal fast which is caused by its day [on the calendar]. And what emerges is also a leniency that in the case of someone who forgot and absent mindedly tastes some food [on a communal fast day] he may resume fasting and will not need to repay it according to the strict letter of the law. Only if he wishes to fast to atone for his error [would there be a value in making it up].

Since communal fast days emerge from a specific date on the calendar, the mitzva is to observe those days to the best of one’s ability. However, there would be  no purpose or possibility to observe the 17th of Tammuz, say, in the middle of Sivan. This is in contradistinction to a personal fast that one accepts voluntarily upon himself which R. Feinstein rules must be made up. Moreover, he adds that if one took a vow to observe a specific date they need to err on the side of caution on both fronts: They must resume fasting immediately and they are required to find a makeup date to fast in completion (see Shulhan Arukh, O.H. 568:1, and Magen Avraham 568:4).

In the scenario of a person who needs to work on a calendaric fast day, R. Feinstein rules that they may not forgo the fast from the outset, unless they experience significant symptoms of illness. This would be true even on Tisha B’Av, which is more severe than the minor fasts (see Shulhan Arukh, O.H. 554:6).

Nonetheless, one would not necessarily be required to take the day off from work, whether they are engaged directly in holy work or whether their time is already committed to an employer who would be negatively impacted by their absence. If the fast causes symptoms to the point that breaking it is necessary, then we may let the chips fall as they may post facto. (The implication of R. Feinstein is that those who are self-employed and can afford the day off should do so and thereby best position themselves to observe the entire fast day.

As we mentioned, earlier in this responsum, R. Feinstein made a noteworthy delineation between the requirement to fast versus the secondary value of fasting as a source of atonement. We will explore this important nuance as we analyze several rulings which elaborate on the place of fasting (or lack thereof) in the repentance process.

Connecting the Iggerot

The aforementioned responsum kicks off a series of consecutive letters printed in Iggerot Moshe in which R. Feinstein was asked to provide counsel on issues of repentance that straddled the line between the halakha, the philosophical, and the pastoral domains.

In Orah Hayyim (vol. 4, #115), R. Feinstein is asked to advise a man who has engaged in homosexual activity. He immediately frames his reply as consisting of both halakha and hizzuk, encouragement or motivation. He seeks to dissuade this individual from further engaging in this activity by noting the punishment it carries. In in his assessment (based on Ran on Nedarim 51a and Sanhedrin 67b), written in 1976, such impulses are unnatural, and such acts negatively impact the stature of the individual as well as his family. (We will explore pushback to this framework in the next section.) R. Feinstein recommends the study of Torah as a mental and spiritual protection. He also attempts to lift the spirits of the inquirer by remarking how this individual has already begun to triumph over his yetzer ha-ra: “For you believe in God and the Thirteen Principles of Faith and the entire Torah.” R. Feinstein’s exhibits a philosophy of repentance which minimizes the excessive dwelling on past behavior and instead recognizes how far one has come in his religious journey. This approach becomes more explicit in the ensuing responsa.

In Orah Hayyim (vol. 4, #116), R. Feinstein is asked by an anonymous man how to repent for masturbation. This individual had apparently expressed an interest in undertaking intense pietistic practices called teshuvat ha-mishkal. The early Medieval pietistic work Sefer Hasidim (#167) propounds that in the lieu of lashes or Divine excision one may inflict upon himself something commensurate to his sin. Ran, in his Discourses (#102), writes that: “True repentance must be teshuvat ha-mishkal (balanced penitence), meaning contrition and remorse equal to the gratification derived from the sin.”

R. Feinstein rejects the sources from Kabbala which inflate the consequences for masturbation out of halakhic proportion. He notes that when Rambam (Hilkhot Sanhedrin 19:2-3; Issurei Biah 21:18) listed the various sins which result in death, the gratuitous spilling of seed did not make the cut. Moreover, R. Feinstein fundamentally objects to the notion of typical people attempting the various forms of fasting and self-flagellation prescribed by proponents of teshuvat ha-mishkal. He argues that even advocates of these methods, such as the Rokeach (Hilkhot Teshuva 6:8), only intended these practices for particularly pious individuals rather than for the general populace. R. Feinstein concludes by asserting that not only does the penitent not need to undergo teshuvat ha-mishkal, but it would be forbidden for him to do so since it would detract from his Torah learning and various other mitzvot that he is already obligated to perform.

R. Feinstein consistently expresses concern that fasting and exotic penitential practices will impede a healthy religious life. In the penultimate responsum of this series (O.H., vol. 4, #117) he advises a presently married woman not to undertake teshuvat ha-mishkal to atone for being intimate with her boss during her single years. He argues that such a measure would be religiously irresponsible as it would prevent her from being there for her husband and children. Rather she should work to internalize her belief in God’s omnipresence, recite a regimen of Psalms, and commit to preventing her daughters from entering workspaces which are prone to producing extramarital relationships. Similar to an earlier responsum, he encourages the inquirer not to dwell on the past and fall into depression but rather to be be-simha—she should rejoice that she has set herself on the right path and that, God willing, she will experience blessings in the future.

While R. Feinstein also mentions that she must confess her sin, he is careful to note that expressing one’s sin is meant to be strictly between the sinner and God, rather than to another human being—even to a rabbi. He emphasizes this point more stridently in the final responsum in this sequence.

In Orah Hayyim, vol. 1, #118, R. Feinstein addresses a similar predicament about a young woman who engaged in a premarital sexual relationship—but this case the woman was not presently married. She was living in a college dormitory and had been intimate with her boyfriend. The challenge here is that this young man has no interest in maturing their purely physical relationship into one of marital partnership. Unsurprisingly, R. Feinstein advises this woman to leave the dormitories immediately and attempt to find a proper spouse, with the promise that God will provide her with the financial capability to make it work. He then proceeds to dispel a misconception that this woman appears to have about confession:

Moreover you need to know that confession is something that one must do quietly before God, may He be blessed, but not before another human being. Praiseworthy is the concealment of sin. For only when there is a necessity to know how to repent whether from a halakhic standpoint or to seek good counsel [would it be appropriate to reveal such matters to another person]. Therefore, it is good that you have written to me since you want to learn how you can save yourself from sin, and also I do not know you. However, without such rationales, it would be forbidden to [gratuitously] reveal one’s sins to another human being. For it is only the peritzei umot ha-olam who reason that by confessing before the priests of their faith that they can atone and are [thereby] permitted to transgress any matter [to their heart’s content]. And the ways of the Torah are the antithesis of this, and Heaven forfend to learn from their practices. For it is only for the benefit of learning the ways of repentance and to discover if there is good counsel to combat the evil inclination that one needs to reveal [sins] to another human being.

While R. Feinstein is very adamant about limiting the revelation of one’s past sinful behavior, he does concede that once this woman has developed a relationship with a potential spouse should she give him general disclosure of her previous deeds, while also qualifying that she is a changed person. (He adds that her Ketuba can still identify her as a betula [virgin], since her husband is aware of her status.) However, such a woman would not be required nor permitted to confess such matters on every initial date she goes on.

R. Feinstein is clear: Confession of a sin must serve a constructive cause. Direct confession to God is a component of repentance. And the instrumental confession of one’s sin to a select human being can enable them to glean advice and learn how to forsake their sinful ways. (It should be noted that R. Feinstein is not addressing “confession” to another person within the context of therapy for the purposes of one’s mental health.)

Challenges to the Iggerot

For the most part, R. Feinstein’s responsa on repentance did not receive significant pushback. Though, we should note, his opposition to extreme forms of penance were not unanimous. For instance, R. Yechiel Yaakov Weinberg recommended teshuvat ha-mishkal for an individual who wanted to atone after committing negligent homicide (Responsa Seridei Eish, vol. 1, #35).

However, as eluded to in the previous section, the responsum which did receive significant critique was his letter to the man who had engaged in homosexual activity. R. Chaim Rapoport, in “Judaism and Homosexuality: An Alternate Rabbinic View” (Hakirah 13), writes:

Some rabbis rely on the view of Rabbi Moshe Feinstein, that appears to deny the challenges that male homosexuals must contend with. This harsh condemnation, which has become the normative position for some Rabbis, has unfortunately brought immense suffering to many people. As a result of such attitudes, in addition to coping with unwanted desires, untold isolation and often being the subjects of mockery and ridicule, those men whose sexual attraction is directed to members of the same gender have to cope with the burden of not being believed and trusted, and being rejected and ostracized, sometimes even by their nearest and dearest. It is excruciatingly painful for a person who suffers when those upon whom he relies for emotional support and solidarity do not validate his innermost feelings or acknowledge the harshness of his predicament.

R. Feinstein’s letter on the topic was written in 1976. While this is certainly one of his later responsa, our understanding of how same-sex attraction emerges has developed. The Torah is immutable, yet our understanding of the metziut, the facts on the ground, can be updated upon the discovery of novel data. It is generally accepted that for most people experiencing same-sex attraction is not a choice. If that responsum had been penned today it seems likely that it would have contained additional layers of sympathy for the individual’s excruciatingly difficult predicament, although in a manner that would not compromise the integrity of his halakhic analysis.

Reflecting on the Iggerot

Throughout R. Feinstein’s responsa on repentance we can detect a common theme in which he places a premium on living a healthy and responsible religious life. Undertaking radical forms of penance will negatively impact most people’s ability to perform other commandments like Torah study and can also have negative ramifications for their spouses and children. Instead, R. Feinstein seems to advise going through the standard formula of confession, remorse and abandonment of the sin. He adds that even if one engages in acts of penance such as fasting, that it is only effective after repentance has been achieved. These methods should only be employed as the icing on the cake for one who wishes to seek further atonement. This is akin to how one need not make up for a communal fast, yet they may elect to do so for the sake of atonement. However, R. Feinstein strongly emphasizes that penance can never replace repentance (see a further articulation of this point in Mesorat Moshe, vol. 2, p. 234, and Kol Ram, vol. 2, p. 492).

This is certainly true regarding the act of confession. For people to think that they can simply declare their sins to a member of the clergy and effortlessly wipe their slate clean is a mockery of both theology and morality. On more than one occasion R. Feinstein was approached by someone who wished to make a donation to Mesivta Tifereth Jerusalem to purge their past sins. R. Feinstein replied that “Charity cannot replace repentance. Only in addition to repentance can it effectuate atonement” (Mesorat Moshe, vol. 4, pp. 452-453). To believe otherwise is akin to contributing the harlot’s wage to the Temple treasury in the hope that such indulgences will counterbalance an otherwise sinful way of life (ibid., p. 513). There are no shortcuts to being a God-fearing Jew, no matter how much one may generously donate to holy causes.

In the above analysis we explored many instances in which individuals expressed profound remorse for their previous actions. R. Feinstein once advised his student, R. Yitzchak Gottleib that there is, however, one thing that a person never regrets:

People do many things in life for which they later have charatah (regret). A person may start a business or some other venture and then the day might come when he regrets ever having undertaken it. He may enter a partnership that later turns sour and he will regret the day he agreed to it. That is how life is. But there is one thing that no one ever regrets. I guarantee you that no one who learns a blatt Gemara, a perek Mishnayos or a pasuk Chumash ever wakes up the next day and tells himself, “I’m sorry I did that.” Never (Shimon Finkelman, Reb Moshe: The Life and Ideals of HaGaon Rabbi Moshe Feinstein [Artscroll], 95-96).

Endnote: See R. Rapoport’s aforementioned article and his book Judaism and Homosexuality: An Authentic Orthodox View (2004) for a further analysis on this topic. In particular, see Iggerot Moshe (E.H., vol. 4, #113) regarding the dissolution of the marriage of a woman who unwittingly married a gay man, and see his comments in Dibberot Moshe (Shabbat, p. 401) regarding same-sex female relations. This topic also makes an appearance in his banning of a manuscript attributed to R. Yehuda ha-Hasid which, from R. Feinstein’s perspective, fails to take a sufficiently resolute position on the Biblical prohibition of homosexual relations (Iggerot Moshe, Y.D., vol. 3, #115).

Moshe Kurtz serves as the Assistant Rabbi of Agudath Sholom in Stamford, CT, is the author of Challenging Assumptions, and hosts the Shu”T First, Ask Questions Later

Prepare ahead for the next column (August 15) on vicarious virtues and punishments: Iggerot Moshe, Y.D., vol. 5, #26.

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