It would be understandable, albeit awkward for him, if Esau had been unable to keep the names of his various wives straight. However, it is the Torah itself that actually changes the names from one place to the next. In this week's Torah reading, one of his wives, specifically the daughter of Ishmael, is referred to as Basemat (Gen. 36:3). However, earlier she had been referred to as Machalat (28:9).  Rashi, commenting on the later verse, addresses the discrepancy. Quoting the Midrash (Sam. ch. 17), he relates that there are three categories of people who receive forgiveness for their sins: a convert, one who ascends to a high position, and a groom upon his marriage. The derivation, he notes, is from the earlier verse, as the name “Machalat” alludes to mechilah, forgiveness. On the day of one’s marriage, a groom’s sins are forgiven. (See also Yerushalmi Bikurim 3:3.)

An exhilarating promise; in truth, the best wedding gift one could ask for. Many questions immediately come to mind: What is the nature of this forgiveness? Does it extend to the bride as well? And perhaps most puzzling of all: why anchor this beautiful teaching in Esau's marriage, of all unions?

Automatic amnesty or precious opportunity?

It is that last point that connects to probably the most significant question about this concept. Is the forgiveness of marriage, or does it represent an opportunity that will manifest itself if the groom is sufficiently penitent? As Esau's marriage is the instructive text, and he is apparently the beneficiary of this expiation, this question becomes inextricably bound with the historical question of whether Esau himself did repent. At the same time, the issue contains its own elements. Whether or not this forgiveness requires repentance should depend on the nature of how it operates and the reasoning behind it.

Accordingly, both factors have received attention in the literature. The issue of Esau's moral status is particularly ambiguous. Most indications are that he remains villainous (see, for example, Bava Batra 16b); the very act of this marriage specifically is the focus of discussion as to how it reflects upon his character. On the surface, it seems that his marriage was a violation of his parents' wishes and values, and in fact, a continuation of his previous behavior in that direction, as Rashi comments explicitly. Worse, the Midrash even contains an opinion that Esau plotted with this step to create an alliance through which he would murder his father. Accordingly, some commentaries assume that there is a dispute among the rabbinic sources, with the statement that his sins were forgiven rejecting these interpretations and instead assuming that he repented (see Yfeh Mareh to the Yerushalmi, 5, s.v. ela) and Yfeh Toar to the Midrash, 10, s.v. natan da’ato).

Consistent with the view that there is a dispute, there is an opinion in the Midrash that his marriage was a step towards religious conversion (see Rabbenu Bachya). While this may make the amnesty more understandable, to some it actually clouds the issue, for if he indeed repented, then presumably forgiveness would flow from that decision without a need to attribute it to a special grace of marriage. R. Chaim Vital (Sefer Eitz HaDaat Tov, II, drushim, ma’amar l’chatan), however, rejects that inference. While repentance can take one a certain distance, there is an additional value that marriage adds that allows the groom to receive a more absolute atonement.

R. Chaim Hezkiyahu Medini in his Sdei Chemed (Asifat Dinim Marekhet Chatan V'Kalah, number 4) draws a distinction between the expiation of the groom and that of one who ascends to a position of prominence (see the extensive comparison of the different categories in Kokhvei Yitzchak, III kvevod melachim #35, and seeMinchat Machavat II, 104.)

Some earlier sources suggest that the groom merits that his sins are actually held in abeyance, and will be held against him if he returns to his old ways. This is also the understanding accepted by the Reisher Rav, R. Aharon Levine (HaDrash v’HaIyun, Gen.# 132), who assumes that amnesty is granted to the groom if he indeed takes on a new path from this point forward. In that case, his previous misdeeds will not be held against him. However, should he return to previous misbehavior, no forgiveness will be granted.

One particularly confounding source is a Talmudic passage (Kiddushin 49b) that is frequently cited during the High Holiday season because of its implications for the immediate transformational potential of repentance. We are taught that if one betroths a woman (halakhic kiddushin, which would require a get to undo) on a stated condition that it should take effect only if he is righteous, that betrothal must be viewed as possibly valid, even if he is known to be thoroughly wicked. This is due to the possibility that he may have had thoughts of penitence that would have affected an immediate atonement.

The question is raised as to how this interacts with the notion that the very act of marriage would itself bring about atonement and render the groom righteous. Given that principle, perhaps we should say that the marriage is certainly valid rather than merely a possibility to be concerned for (see the discussion in Resp. Nezer HaKodesh, 97). This raises the question of whether the betrothal phase of marriage, without the second phase of nisuin, that completes the union, should actually accomplish the atonement; the Pri Megadim (OC 573) was confident that it would not (see also Palgei Mayim al haTorah, pp. 218-220). Given that the full responsibilities of marriage do not attach until that second phase, that position may indicate something about the logic of the atonement.

Alternatively, this may shed light on the character of the atonement. Perhaps the betrothal would effect the promised atonement, but would not render the groom completely “righteous”. It is that latter status that would require actual repentance (see Chedvat Yotzer, I pp. 48-50). In this case, the implication is that the atonement of the groom is an act of grace rather than an indication that marriage itself serves as an act of repentance.

This passage may actually prove relevant in a different direction. The Lechem Mishneh (Hil. Ishut 8:5) asked, if one must factor in the possibility of instantaneous repentant conversion, no wedding should ever be invalidated due to unqualified witnesses; perhaps they too had thoughts of repentance. To this, some respond that the possibility is present only regarding the groom, as it is due to the special grace extended to him on the day of his marriage. That, in conjunction with thoughts of penitence, could render him righteous. No such possibility exists regarding the witnesses. (Resp. Dovev Meisharim, I, 22; Kotzker Rebbe, cited in Siach Sarfei Kodesh, IV, #15)

This discussion is not merely academic; it has practical relevance. There is a widespread custom for the bride and groom to fast on the day of their wedding (Rama, EH 61:1). One prominent explanation for this is that it is connected to the forgiveness that the groom attains on that day (Resp. Maharam Mintz, 109, quoted in Beit Shmuel and in Magen Avraham, OC, 573). Through that grace, it becomes a personal Yom Kippur. That is the background to a number of familiar customs, such as the recitation of viduy, the confession of sins, before the chuppah. However, if indeed the amnesty is automatic, these practices are difficult to understand; one should celebrate, rather than fast (see Resp. Torat Yekutiel, 92). The custom to fast and to take on practices of atonement indicate an understanding that the forgiveness is not automatic, but rather represents an opportunity to be realized should the groom rise to the occasion through acts of repentance and personal change. (For further extensive discussions, see Chamudei Yitzchak and Palgei Mayim to Gen.)

Theories of the Atonement

These questions transition naturally into an even more fundamental question: what is the basis for this grace? Why should a groom be forgiven?

R. Avraham Shemuel Binyamin Sofer, the Ketav Sofer, notes in his commentary to the Torah the Talmudic statement that "one who exists without a wife exists without a wall"—that is, a wife is a spiritual protector, particularly in isolating her husband from temptations of a licentious nature. One who marries, therefore, is taking a proactive measure to protect himself from sin, and simultaneously establishing the defense that previous iniquities were due to the single status he is now abandoning. Such an act is thus to be viewed as repentant and thus earns amnesty.

A broader explanation is offered by R. Yehoshua Falk (Perishah, EH, 1), who notes simply that the forgiveness is earned by fulfilling God's will. More specifically, writes R. Shimon Sofer (Resp. Hitorrerut Teshuvah, EH, 25), the groom is meritoriously involved in populating the world. The commentary Yefei Mar'ehoffers a two-pronged suggestion: either the intent to lead a family in righteousness is sufficient to earn atonement, or the merit involved in attaining such an opportunity is indicative of an accepted repentance.

R. Sofer's grandson, R. Akiva Menachem Sofer, connects the groom to one of the others who receives forgiveness—"one who ascends to greatness." The Rabbis teach (Pirkei D'R' Eliezer, ch. 16) "a groom is comparable to a king;" thus one who marries is similar to one who becomes royalty. “A groom is comparable to a king.” A new king or communal leader also receives forgiveness, not as a private favor but because the community needs a leader who can function without the paralytic weight of past sins. In the intimate kingdom of the home, the groom likewise becomes a kind of monarch. He, too, is granted a new beginning so that he can carry the responsibilities of marriage and family with clarity and confidence.

Alternatively, R. A. M. Sofer suggests linking the groom to yet another of his partners in atonement: the convert. This he does in the name of the Maharal of Prague (Netivot Olam, II, Netiv HaAnavah, ch. 6), who writes that the convert who receives forgiveness for his conversion undergoes a complete personal transformation and is, in the Talmud's words, "as a newborn child." So too, a single man is incomplete (Yevamot 63a); his marriage is a completion and thus a transformation, acquiring for him a clean slate, spiritually (see Lev Tahor to Gen. for practical implications of this position).

Does the Bride Receive Atonement?

The Midrashic passage specifically states that the groom is forgiven. But what about the bride? The sources that discuss fasting also include the bride, indicating they are both understood to receive atonement. Other sources, however, maintain that it applies to the groom alone, as the language of the Talmud suggests; nonetheless, the Magen Avraham(OC 573) indicates that it applies to the bride also, followed by the Sha’arei Teshuvah and the Mishnah Berurah. Practically speaking, the custom is that they both fast.

The Buchacher Rav, in his Eishel Avraham (OC 573), notes that while it is true that the early sources only refer to the groom when discussing the atonement, it is logical to assume that it should apply to the bride also, whose role in this mitzvah is crucial.  R. Avraham Yitzchak Glick (Resp. Yad Yitzchak II, 103) takes it a step further. If indeed the Torah was to change someone's name in order to convey the message that an atonement was being granted, why was it the bride's name that was impacted rather than the groom's? He suggests that in fact, considering the rabbinic tradition that the father of the bride in this case, Ishmael, had himself repented, one must also presume that he was only willing to allow his daughter to marry one who would be willing to walk the path of righteousness, and that that was her desire as well. Accordingly, the atonement that took place was due to the constructive influence that this new bride exerted upon Esau. That, he suggests, is why the form of the word is “Machalat” in order to convey that this was a reality she brought about on behalf of Esau.

A responsum of the Klausenberger Rebbe (Divrei Yatziv, E.H., 72) indicates a very different understanding of the subtext of the biblical narrative. Nonetheless, his conceptual and practical conclusion is similar and importantly instructive. If the bride is playing a constructive role in creating an idealistic and spiritually ambitious future for the husband, then indeed this will bring a redemption for him, and certainly earn her an equal share in that.

A Wedding as Hope

The doctrine that a groom receives forgiveness on his wedding day ultimately reflects an optimistic theology. Marriage in Jewish thought centers on the future: children, community, the building of a Jewish home. The atonement granted on the wedding day is thus forward-looking. It teaches that whatever you have been, from this moment you can be something new. Your past need not define your future. The home you are about to build, the family you aspire to raise—all of this creates the possibility of transformation. The Chuppah is a spiritual reset button, and a genuine threshold, if one walks toward it with purpose.