בס”ד

Mrs. Doubtfire: A Halachic Movie Review

Introduction

Mrs. Doubtfire is a 1993 comedy starring Robin Williams. The film tells the story of Daniel Hillard, a struggling voice actor and father of three whose marriage falls apart. Following a difficult divorce, Daniel loses custody of his children and is granted only limited, supervised visitation.

Desperate to spend more time with his kids, Daniel devises an elaborate plan: he disguises himself as a nanny named “Mrs. Doubtfire” and applies for a housekeeping position with his ex-wife. Incredibly, the plan succeeds.

While the film is widely remembered for its humor and heart, it raises several ethical questions – ranging from deception to scenes that some viewers have critiqued as racially insensitive or transphobic. In this article, however, I would like to focus on a specific halachic concern: the prohibition of cross-dressing.

Was Daniel Hillard halachically permitted to disguise himself as a woman in order to spend time with his children?

The Prohibition of Cross-Dressing

The Torah (Deuteronomy 22:5) states:

A man’s garment shall not be upon a woman, and a man shall not wear a woman’s garment, for the abomination of the L-rd your G-d are all who do these.¹

The Torah explicitly provides a reason for this prohibition, stating that it is a toevah – an abomination. In biblical usage, the term toevah is associated with either forbidden sexual behavior or idolatry. Indeed, both of these explanations are offered by the commentaries.²

The Sefer HaChinuch, for example, writes:

It is from the roots of the commandment [that it is] to distance our holy nation from matters of sexual immorality and any matter and any angle whatsoever that contains a stumbling block towards it — as the matter that they, may their memory be blessed, said metaphorically (Sanhedrin 106a) that our God hates promiscuity. [This] means to say, that in His love for us, He distanced us from promiscuity, which is an exceedingly ugly thing, [and which] takes the heart of a man and pushes it off from the good path and from desirable thoughts, to a bad path and thoughts of stupidity. And there is no doubt that if the clothes of men and women were the same, they would constantly mix — these with those — “and the world would be filled with promiscuity.” And they also said in explaining this commandment that it is to distance all matters of idolatry, as the way of the worshipers of idolatry was with this. And I found these two reasons in the books of Rambam (Sefer HaMitzvot, Negative Commandments 40; Guide for the Perplexed 3:37) after I wrote them.³

The rationale for prohibiting cross-dressing as a safeguard against illicit interaction is straightforward. In societies with strong norms of gender separation, cross-dressing could function as a form of disguise, granting access to spaces reserved for the opposite gender – potentially for inappropriate or exploitative purposes. By blurring gender distinctions, one might create opportunities for prohibited relationships.

This idea is echoed in the Talmud, Nazir 59a:

“A woman shall not wear that which pertains to a man, and a man shall not put on a woman’s garment, for whoever does these things is an abomination to the Lord your God” (Deuteronomy 22:5). What is the meaning when the verse states this? If it teaches only that a man may not put on a woman’s garment, and a woman may not wear a man’s garment, it is already stated in explanation of this prohibition that “it is an abomination to the Lord your God,” and there is no abomination here in the mere act of wearing a garment.
Rather, it means that a man may not wear a woman’s garment and thereby go and sit among the women; and a woman may not wear a man’s garment and sit among the men.⁴

This understanding of the verse – that a man may not wear women’s clothing in order to sit among women – is presented anonymously. It is typically referred to as the Tanna Kama, meaning the unnamed first opinion. The Talmud then follows by citing the view of Rabbi Eliezer ben Yaakov:

Rabbi Eliezer ben Ya’akov says: From where is it derived that a woman may not go out with weapons to war? The verse states: “A woman shall not wear that which pertains to a man, and a man shall not put on a woman’s garment,” which indicates that a man may not adorn himself with the cosmetics and ornaments of a woman, and similarly a woman may not go out with weapons to war, as those are for the use of males.

Understanding the Disagreement

Rabbi Joseph Karo, author of the Shulchan Arukh (the code of Jewish law), understood the Talmud as presenting a fundamental dispute.⁵ According to the Tanna Kama, the prohibition of cross-dressing applies only when it is done for the purpose of entering the company of the opposite gender for illicit or promiscuous purposes. According to Rabbi Eliezer ben Yaakov, by contrast, the prohibition applies even without sexual intent.

The Position of the Tanna Kama

The Tanna Kama appears to maintain that the prohibition of cross-dressing does not target the clothing itself, but rather the breach of gendered spaces that such clothing enables. The concern is that cross-dressing may serve as a tool to facilitate inappropriate sexual behavior. According to this view, cross-dressing is only prohibited when it functions as a means toward that end.

This position becomes more understandable when considered in light of societal norms in ancient times. For example, under Roman rule – particularly during the reign of Emperor Trajan – women rarely left the home; even shopping was typically done by their husbands.⁶ We find a reflection of this mindset in the words of Maimonides:

[He must give her this veil] so that she can visit her father’s home, a house of mourning or a wedding celebration. For every woman should be given the opportunity to visit her father and to go to a house of mourning or a wedding celebration as an expression of kindness to her friends and relatives, for [this will have a reciprocal effect], and they will return the visits. For a woman [at home] is not confined in a jail, from which she cannot come and go.
Nevertheless, it is uncouth for a woman always to leave home – this time to go out and another time to go on the street. Indeed, a husband should prevent a wife from doing this and not allow her to go out more than once or twice a month, as is necessary. For there is nothing more attractive for a woman than to sit in the corner of her home.⁷

Gender separation appears to have been a deeply rooted reality. Fear and suspicion surrounding cross-dressing and the blurring of gender boundaries are reflected in rabbinic texts, including poems and stories from the Middle Ages.⁸ For example, Rabbi Judah ben Solomon Al-Harizi, a 13th-century rabbi, translator, and poet, tells a story in Tachkemoni (Gate 31) in which a group of travelers in the desert encounter a beautiful woman and, moved by compassion, allow her to join them. Later, she murders one of them, and they discover that the ‘woman’ was in fact a man in disguise.

Given the reality of gender segregation in earlier societies, it seems almost self-evident that someone who cross-dressed would do so in order to gain access to spaces designated for the opposite gender. As Rabbi Baruch Meir Yaakov Shochet, the current Rebbe of Karlin-Stolin, once quipped when asked whether the prohibition applies only when one cross-dresses with the intent to enter the other gender’s space: “Of course he intends to go to the women’s side – no one’s letting him into the men’s section if he looks like a woman!”⁹

In such a society, it is easy to understand how a man intent on illicit behavior might cross-dress to gain access to women’s spaces. By contrast, in contemporary society – where gender segregation is far less common – cross-dressing as a means of sexual access is rare and counterproductive. If someone were intent on promiscuity, it would be far easier to go to a bar than to impersonate a woman. Thus, the prohibition would rarely apply in modern contexts and would be relevant only in exceptional cases.

The Position of Rabbi Eliezer ben Ya’akov

Nonetheless, Rabbi Joseph Karo stresses that according to Rabbi Eliezer ben Yaakov, the prohibition applies even when there is no intent to blur gender roles and engage in misconduct. The act of wearing clothing associated with the opposite gender is prohibited, regardless of context, intent, or purpose.

Although there are halachic authorities that seem to follow the view of the Tanna Kama,¹⁰ the accepted halacha follows Rabbi Eliezer ben Yaakov. Accordingly, one who cross-dresses – even absent any intent for deception or promiscuity – would still transgress this prohibition.

Another Approach

However, one could argue that both Rabbi Eliezer ben Yaakov and the Tanna Kama agree that cross-dressing is only forbidden when done with the intention of sexual promiscuity. While they may disagree about which actions constitute a violation, they might both hold that intent is a key factor.

According to this interpretation, the Tanna Kama would permit a woman to wear military gear, whereas Rabbi Eliezer ben Yaakov would not. Still, both might agree that if the act is not done with improper sexual motives, it would not be prohibited.

Wearing military attire may likewise serve as a means of accessing male spaces and could be motivated by improper intent. A woman seeking to enter male spaces could do so by joining a war zone or other combat setting.¹¹ The Ibn Ezra writes:

If a woman joins men in going to war she will come to engage in illicit sexual relations on the way.¹²

Similarly, Rabbi Bahya ben Asher:

The principal concern of our verse is to deny the woman the right to bear arms (Sifri 227, Nazir 59). She is not to go to war and become a cause for immorality rampant during war. Similar considerations, i.e. the prevention of creating opportunities for sexual promiscuity – are the reason males are forbidden to wear women’s garments.¹³

There are also examples of cross-dressing behaviors that would be forbidden for men according to Rabbi Eliezer ben Yaakov but allowed by the Tanna Kama – such as wearing women’s jewelry. The Sifrei (Ki Tetze) states:

R. Eliezer b. Yaakov says: Whence is it derived that a woman may not go out with armor to war? From “A man’s vestment shall not be upon a woman.” And whence is it derived that a man may not adorn himself with the adornments of women? From (Ibid.) “and a man shall not wear a woman’s garment. For the abomination of the L-rd your G-d are all who do these.”¹⁴

According to Rabbi Eliezer ben Yaakov, it is prohibited for a man to adorn himself with women’s jewelry. The motivation in such cases might be to attract women, or possibly to pursue homosexual relationships.¹⁵ In either case, the intent is sexual, which would render the behavior forbidden.

Why Do They Disagree?

From the Talmud, it appears that their disagreement centers on which types of dress fall under the prohibition. All the cases where they diverge involve actions not strictly related to clothing.

Another example of disagreement between the two concerns the removal of hair from private areas. According to the Tanna Kama, this can only be prohibited rabbinically, whereas Rabbi Eliezer ben Yaakov could maintain that it constitutes a biblical violation.

The Torah explicitly forbids wearing the garments of the opposite sex. In the cases of military gear, jewelry, or body grooming, no actual “garment” is involved. According to the Tanna Kama, this would fall outside the scope of the biblical prohibition.

Rabbi Eliezer ben Yaakov, however, adopts a broader interpretation. He includes all forms of cross-dressing under the prohibition, even when they do not involve actual garments. Accordingly, he rules that a woman may not bear arms, a man may not wear women’s adornments, nor may he groom in ways associated with the opposite gender, such as shaving the armpits or private areas. Nevertheless, he too maintains that the prohibition applies only when done with promiscuous intent.

This interpretation is supported by Rabbi Moses ben Jacob of Coucy, a 13th-century rabbi, in his Sefer Mitzvot Gadol¹⁶ (known by its acronym, Smag). He acknowledges that while there is debate over what constitutes cross-dressing, Rabbi Eliezer ben Yaakov does not fundamentally disagree with the premise presented by the Tanna Kama. He emphasizes that the verse cannot be entirely divorced from its plain meaning – seemingly referencing the fact that it describes cross-dressing as an “abomination,” a term often associated with sexual immorality.¹⁷

Following this Rabbi Isaac ben Joseph of Corbeil – also a 13th century authority – in his sefer mitzvot katan, an abridgment of the Sefer Mitzvot Gadol, writes on this commandment (Mitzvah 33):

“a man shall not wear a woman’s garment” – meaning in order to have an illicit affair.

To Rabbi Moses of Coucy it appears clear that while there may be disagreement over what actions constitute cross-dressing, the premise that the prohibition applies only when done with sexual intent is not in dispute. Both opinions agree that without that intention, there is no biblical violation.

Costumes on Purim

There has been a longstanding halachic debate regarding cross-dressing for the sake of costumes during joyous occasions. We find many such practices amongst jewish communities on holidays like Shavuot, Chanukah, Simchat Torah, and most notably, Purim.¹⁸ This custom extends to other celebratory events such as weddings and graduation ceremonies. For example: “in Egypt the bride was decked with helmet and sword, while the groom and his escort wore feminine garments and colored their finger-nails with henna, as women did.”¹⁹

This practice sparked halachic debates in many jewish communities throughout the ages, with rabbis who opposed it and those that defended it.

One particularly notable example of crossdressing on purim, is from a poem of Kalonymus ben Kalonymus, a rabbi, philosopher, and poet of the late 13th and early 14th centuries.

Kalonymus ben Kalonymus is best known for his work Even Boḥan, particularly for a striking poem in which he laments having been born male – a passage that has led some scholars, such as Tova Rosen,²⁰ to suggest that he suffered from gender dysphoria. Kalonymus also had a deep fondness for Purim; he authored a Talmudic parody titled Masekhet Purim.²¹ The combination of these two traits makes the topic of cross-gendered Purim costumes particularly interesting. Indeed, in Even Boḥan,²² while describing the joy and festivities of Purim, Kalonymus mentions the practice, writing: “…this one wears a woman’s dress…”

Purim, in particular, became associated with various questionable behaviors carried out in the spirit of the holiday – many of which attracted halachic scrutiny and debate. One such practice involved people taking food from one another without asking permission. Rabbi Tobiah ben Eijah of Vienne (Burgundy), a 13th-century French Tosafist, addressed this issue. He quoted Rabbi Isaac ben Abraham of Dampierre, a prominent Tosafist of the late 12th century – an older contemporary and possibly also his teacher²³ – as permitting the custom, provided it was done in accordance with the local authorities.²⁴

A similar debate emerged regarding Purim costumes that contained both wool and linen – violating the prohibition of shatnez. According to Jewish law, garments made from a mixture of wool and linen are forbidden; in some cases, the prohibition is biblical, though more commonly it is rabbinic, depending on how the materials are woven or combined.

In the 15th century, the issue became a subject of halachic controversy, as concerns arose over Purim costumes that were rabbinically prohibited due to their shatnez content. Rabbi Aaron HaLevi Tzion, often referred to as Zelikman of Binga, initially suggested that the practice should be permissible, but then challenged this view, citing the hesitation of his teacher and father-in-law, Rabbi Yaakov ben Moshe Levi Moelin, the Maharil, regarding the custom.²⁵ Similarly, Rabbi Israel of Bruna, a major 15th-century authority, is also quoted as opposing the practice.²⁶

A similar debate arose regarding the custom of crossdressing on Purim. The tradition of wearing costumes led to men dressing as women and vice versa, sparking halachic controversy. In 15th-century Greece, two leading rabbis disagreed on the matter. Rabbi Elyakim Segal, the rabbi in Corfu, ruled that the practice was permissible, while Rabbi Gershon Bonifacio, Rosh Yeshiva there, as well as a rabbi at some point in Chania, maintained that it was forbidden.²⁷

This dispute was addressed by Rabbi Judah ben Eliezer ha-Levi Minz,²⁸ a prominent halachic authority and contemporary of the two. He did not regard Rabbi Gershon favorably; in one responsum, he described him as a sinful individual who should not be treated as a halachic authority.²⁹ In this responsum as well, he criticized Rabbi Gershon’s position. Rabbi Judah argued that if the practice were truly prohibited, earlier sages would have opposed it. Instead, he defended the custom and offered two halachic justifications for permitting crossdressing on Purim in the context of costumes. His first argument was that intent matters when it comes to crossdressing, and on Purim, the intent is simply to celebrate and enjoy the holiday. Rabbi Judah cites Rabbi Moshe of Coucy, who maintained that crossdressing is only forbidden when done with promiscuous intent.

Rabbi Judah also drew parallels to other Purim-related leniencies, such as taking food without permission or wearing garments with questionable shatnez content, concluding that cross-dressing, too, is permitted when done for the joy of the holiday and without improper intent.

This position was later codified in the Shulchan Aruch, the code of jewish law. The Rema writes:

The custom of wearing masks on Purim, and of crossdressing, is totally permitted because of its innocent and joyful purpose, as is the wearing of shaatnez. While some would prohibit it, our practice is as I have already said. So too those who playfully rob each other do not violate “Thou shalt not steal”, and such is our custom. However, you may do only as local elders permit.³⁰

The Graduation Ceremony

An interesting case arose in 17th-century Amsterdam, where students customarily celebrated graduation with festivities that often included crossdressing as part of their costumes. When such celebrations coincided with Simchat Torah, controversy erupted, with some protesting the practice as sinful. The matter was brought before Rabbi Isaac ben Abraham Uziel, a Moroccan-born scholar who had moved to Amsterdam in 1606 and, just four years later, became the rabbi of the Portuguese exile community “Neveh Shalom.”³¹

Rabbi Uziel was not only a respected authority in traditional Torah scholarship but also a poet, philosopher, and mathematician. He also authored a book on Hebrew grammar titled Ma’aneh Lashon.³² In addressing the issue, he sent a letter to several leading rabbis of the time, seeking their halachic opinion and guidance. In his letter, he noted that this custom of crossdressing in celebration was widespread and had long been practiced in Italy, Germany, and Western Turkey. He specifically mentioned that in Constantinople – home to one of the largest Jewish communities – crossdressing had been part of wedding celebrations for generations. Importantly, he emphasized that this custom had never been met with halachic objection by the local rabbis.³³

He received a response from Rabbi Abraham ben Solomon Alegre, a rabbi in Constantinople,³⁴ who wrote that while the majority of rabbis permitted the practice, he ruled against it. He reviewed Rabbi Judah Minz’s arguments and rejected his halachic reasoning. According to Rabbi Alegre, the strongest argument Rabbi Judah presented was the custom’s longstanding precedent; however, even this, in his view, was insufficient to justify crossdressing, which he considered in this case to be a biblical transgression.³⁵

However, Rabbi Joshua Raphael ben Israel Benveniste, also of Constantinople and a student of Rabbi Uziel in Hebrew grammar,³⁶ responded by defending the custom. He supported maintaining the tradition and cited similar practices in Egypt. In his defense, he emphasized that the permissibility depends on intent, arguing that crossdressing is allowed when not done with promiscuous purpose.³⁷

Similarly, the rabbis of Venice signed a petition in support of the practice. One rabbi even remarked that he had reviewed the matter thoroughly and found no violation of any prohibition, humorously noting that “Thou shalt not laugh” is not among the 365 negative commandments.³⁸

Rabbi Chaim Benveniste, Joshua’s younger brother, later recalled this controversy in his halachic work, Keneset ha-Gedolah (on Beit Yosef, in Orach Chaim 695, 4) He recounted that the rabbinic consensus at the time supported the custom. He cited Rabbi Yeḥiel Bassan, a leading Turkish halachic authority and colleague of Rabbi Abraham Alegre, who also approved of it. Notably, Rabbi Chaim himself disagreed with the permissive ruling.

Many prominent rabbis accepted cross-dressing on Purim as halachically permissible,³⁹ and some even offered mystical explanations for the custom. For instance, Rabbi Avraham Yehoshu‘a Heshel, founder of the Apt hasidic dynasty,⁴⁰ writes in his Ohev Yisra’el (Purim, Zhytomyr, p. 44a), that Purim is a time of joy rooted in opposites. He references the verse describing the miracle of Purim: “the enemies of the Jews had expected to get them in their power, the opposite happened, and the Jews got their enemies in their power.”⁴¹ Rabbi Heshel explains that the joy of the holiday arises from subverting the ordinary, and reversing expectations. This, explains the joy associated with cross-dressing on Purim: “As we see that on Purim, when a man puts on a woman’s dress, people become happy and joyful as a result—but when women wear it the entire year, it does not create joy.”⁴²

In light of all this, there appears to be a strong halachic basis for the view that the prohibition against cross-dressing does not apply when the act is motivated by non-sexual intentions.⁴³ Accordingly, one could reasonably argue that Daniel Hillard did not violate this prohibition.

Rabbinic Consensus

I have heard firsthand accounts of cross-gendered costumes being worn on Purim by ultra-Orthodox rabbis. Nevertheless, the majority of halachic authorities have not accepted this practice, and it is generally forbidden.

Among those who prohibit cross-dressing on Purim, some maintain that it violates the biblical prohibition.⁴⁴ These rabbis seemingly follow Rabbi Joseph Karo’s understanding of the Talmud, according to which the prohibition applies even if there is no intent of promiscuity.

However, many others who prohibit the practice do not consider it a biblical violation. These authorities appear to follow the Rema’s understanding of the Talmud, that the prohibition applies only when there is sexual intent.

Some rabbis maintain that, although it may not violate a Torah prohibition, it remains forbidden on a rabbinic level.⁴⁵ There are even those who accept the Rema’s ruling but understand him to mean that cross-dressing is still rabbinically prohibited even without improper intent, and that the rabbinic prohibition is simply waived for the festivities of Purim.⁴⁶ I am not entirely convinced by that interpretation.

Others maintain that crossdressing does not constitute a biblical or rabbinic violation per se, but the practice should still be avoided.

Rabbi Moses Ḥagiz, an 18th-century rabbinic authority known both for his prolific writings and his staunch opposition to Sabbateanism,⁴⁷ addressed the custom of wearing masks and costumes on Purim in his work Elleh ha-Mitzvot (Jerusalem, p. 293). After offering a mystical explanation for the practice, he concluded that it is fitting and proper for people to choose costumes that do not involve crossdressing, as such attire can still fulfill the spiritual purpose of the custom.

Rabbi Isaiah ben Abraham Ha-Levi Horowitz, one of the foremost halachic authorities of the late 16th and early 17th centuries,⁴⁸ addresses the matter in his magnum opus, Shenei Luchot HaBerit (Amsterdam, p. 261b) After bringing the Rema’s permissive ruling regarding cross-dressing on Purim, he adds his own firm objection: “However I say, this is not the law for the pious, and one who wishes to guard his soul, should distance himself from this!”

Similarly, Rabbi Jehiel Michal ben Aaron Isaac Ha-Levi Epstein, a major 19th-century halachic authority,⁴⁹ rejects the leniency outright in his Arukh HaShulchan (Orach Chaim 696:12). He argues that the Rema permitted the practice only to account for the prevailing custom of his own time – a justification that, in his view, no longer applies. To explain the shift and why the leniency is no longer appropriate, Rabbi Epstein wrote: “Now, all joy is negated” or “darkened”.

Rabbinic Prohibition

Rabbi Moses of Coucy’s position – that one is not biblically liable for cross-dressing without sexual intent – continues to hold water. Many rabbis seem to agree with this view and rule that if the act is motivated by an ulterior, non-sexual purpose – such as costuming – it does not violate Torah law. The Rema and Rabbi Judah of Minz permitted cross-dressing on Purim for this reason, and many rabbis who opposed this custom, accepted this halachic reasoning.

This permissibility, however, appears to apply only to Purim, not to other cases of non-sexual cross-dressing. I believe the distinction lies in the perception of the act. On Purim, it is clear that the costume is not an attempt to present as the opposite gender, but rather part of the communal celebration.⁵⁰ A comparable modern case would be that of a male actor playing a female role. Here too, it is evident that the individual is not attempting to deceive or appear as a woman, but is simply performing. This would seem to be entirely permissible.

Outside that context, however, cross-dressing without an evident ulterior motive may cause one to be perceived as violating the Torah prohibition, even if no actual biblical transgression has occurred.

If a man’s appearance causes him to be perceived as a woman, the Rema’s leniency would no longer apply. While such a case may not constitute a violation of the biblical prohibition, the act could still be rabbinically forbidden. The rationale is that, even without the specific intent required for biblical transgression, he is nonetheless engaging in the very behavior the Torah seeks to prevent.

Rabbi Ḥayyim Benveniste argued that even according to Rabbi Moshe of Coucy – who maintained that intent is necessary for biblical liability – the act remains prohibited absent that intent. In his view, the requirement of intent relates only to the imposition of punishment, not to the permissibility of the act itself. Based on this reasoning, Rabbi Benveniste held that even cross-dressing on Purim, though clearly non-promiscuous in nature, would still constitute a violation.

As discussed earlier, there is a strong case to be made that when the non-promiscuous nature of the act is clearly evident, it may be permitted. However, in situations where intent cannot be confidently determined, a rabbinic prohibition may still apply.

Broader halachic considerations must also be taken into account. Even if an act is technically permissible, it may still be forbidden if it creates the appearance of committing a sin. When a prohibition is intent-dependent but intent cannot be externally verified, halacha may prohibit the act entirely. This concern is relevant when a man’s appearance causes him to be perceived as a woman; in such cases, even without improper intent, the halachic system may still treat the behavior as prohibited, since there is no way to confirm that his motives are pure.

Beautification

The Rema allowed cross-gendered costumes on Purim – but this ruling may not extend to acts of adornment, such as wearing jewelry or applying makeup in front of a mirror. While wearing a woman’s garment may be permitted in the context of a costume, beautifying oneself might be forbidden even without promiscuous intent.

The Talmud states:

One who collects and plucks white hairs from among black ones is liable even if he removed a single hair… This matter of plucking white hairs is prohibited for men even on weekdays, as it is stated: “A woman shall not don a man’s clothes, and a man shall not wear a woman’s garment” (Deuteronomy 22:5). The Sages derive that any action typically performed by women for beautification is prohibited for men.⁵¹

It is forbidden for a man to pluck out his occasional white hairs in order to make himself look younger or more attractive. The very act of trying to enhance one’s appearance in this way is considered a form of crossdressing for a man, as it follows the manner of women. This seems to be a biblical prohibition.⁵²

We find other forms of beautification that are seemingly prohibited only on a rabbinic level, such as looking in a mirror or shaving private areas.⁵³

From the Talmud (Nazir 59a), it can be derived that actions which Rabbi Eliezer ben Yaakov would prohibit on a biblical level, would also be prohibited by the Tanna Kama – albeit only rabbinically. For example, Rabbi Eliezer might consider shaving private areas a biblical transgression, the Tanna Kama forbids the same act, though on rabbinic grounds only.

This suggests that beautification is prohibited in and of itself, even without any intent of promiscuity. Accordingly, practices such as looking in a mirror may be forbidden for men, even if they are not done for sexual purposes.⁵⁴

The Talmud addresses the prohibition of male beautification in the context of hair removal and the use of mirrors.⁵⁵ However, it does not present this as a universal rule applying to all forms of adornment, nor is such a principle explicitly stated in the Shulchan Aruch. Nevertheless, one could reasonably extrapolate a broader principle from these examples. Rabbi Joel ben Samuel Sirkis, a major early 17th-century halachic authority, in his work Bayit Chadash,⁵⁶ as well as Rabbi Samuel ben Abraham Aboab (Sefer ha-Zikhronot, p. 15a) a prominent 17th century halachic authority, applied this reasoning more broadly. They ruled that all forms of male adornment are prohibited on rabbinic grounds, even in the absence of promiscuous intent. In their view, just as the Tanna Kama forbids practices such as plucking white hairs or shaving private areas, and just as looking in a mirror is prohibited regardless of motivation, so too any act of beautification by a man is deemed rabbinically forbidden—even when performed with entirely innocent intent.

While this is not conclusive,⁵⁷ it is intuitively sound, and should be taken into consideration.⁵⁸

Conclusion

It appears that the biblical prohibition against cross-dressing applies only when the act is motivated by illicit sexual intent. On that basis, one could argue that Daniel Hillard does not violate the biblical commandment, as his purpose in dressing as Mrs. Doubtfire is to maintain a relationship with his children.

There is however a very strong argument to be made according to which it would still be forbidden rabbinically. Whether because it is forbidden to crossdress unless it is clear that his intent is pure, alternatively, because he adorned himself, or simply because even absent any promiscuous intent, cross-dressing may still be rabbinically forbidden.

Incurring a Great Loss

In halacha, commandments are divided into two main categories: positive commandments, which usually require an action, like, putting on tefillin, and negative commandments, which generally forbid specific actions, like stealing. The general principle is that one is not required to incur a massive loss to fulfill a positive commandment. However, to avoid violating a negative commandment, one is obligated to forfeit everything they own.

The Rema writes in Shulchan Arukh, the code of jewish law:

Somebody who doesn’t have an etrog or some other [objected associated with a] mitzvah whose time will elapse need not dispense much wealth on it, as they said, “One who dispenses [money to charity] should not dispense more than one-fifth [of their wealth]” [Ketubot 50a], even with respect to a mitzvah with a time that will elapse (Ros”h, Rabbeinu Yerucham 13:2). This specifically applies to a positive mitzvah. However, regarding a negative mitzvah, one should spend all of their wealth rather than sin (Rashb”a and Raavad).⁵⁹

One does not need to “dispense much wealth” to fulfill a positive commandment.

While the threshold of “much wealth” is not precisely defined, many authorities include certain non-monetary losses under this category – such as losing a spouse⁶⁰ or being unable to find one.⁶¹

Rabbi Moshe Feinstein wrote that preserving one’s mental health surpasses even great monetary loss, since people would sacrifice all they have to maintain psychological well-being.⁶²

It would seem to me that a father losing a meaningful relationship with his children – as in Daniel Hillard’s case – could certainly qualify as a significant loss. This is evident from the length he went through to spend time with them.

However, the prohibition of cross-dressing is a negative commandment, and one is obligated to incur even great personal loss to avoid such prohibitions. But, as explained above, the biblical prohibition does not apply to Daniel’s case due to the lack of promiscuous intent, then at most he would be transgressing a rabbinic prohibition.

This raises a pivotal question:
Must one suffer a great loss to avoid violating a rabbinic prohibition?

If the answer is yes, Daniel would be halachically required to abandon his disguise, even at the cost of losing access to his children. But if one is not required to incur such loss to avoid rabbinic violations, then his actions might be permitted.

Some halachic authorities have argued that rabbinic prohibitions, being of lesser severity than positive biblical commandments, do not demand such sacrifice.⁶³ Others have distinguished between universal prohibitions, which apply to all Jews, and non-universal prohibitions, which do not. Only the former, they argue, would require someone to incur a great loss to avoid transgression.⁶⁴

In Daniel’s case, both leniencies might apply:⁶⁵ The prohibition is rabbinic, and it is non-universal, since it applies only to men, not women.⁶⁶

However, the majority of halachic authorities reject leniency in such cases.⁶⁷ For example, the Shulchan Aruch Harav, (Orach Chaim 329:7) rules:

When, by contrast, [thieves] come to take an individual’s money, he should allow them to take everything he has and not desecrate the Shabbos, not even [by overstepping] a Rabbinic safeguard.⁶⁸

Given this, I am hesitant to outright permit Daniel Hillard to cross-dress in order to spend time with his children.

However, if he has already undertaken the disguise and now seeks guidance on whether he must immediately remove the costume, I believe he is not obligated to do so. Instead, he may continue as Mrs. Doubtfire for the remainder of the day, and upon returning home, he should quietly change out of the costume – preserving his dignity and avoiding unnecessary embarrassment.⁶⁹

Talmudinfo

1
Translation based on: The Rashi chumash by Rabbi Shraga Silverstein.
2
Regarding the illicit sexual concern, see; Ibn Ezra on Deuteronomy 22:5 (H. Norman Strickman and Arthur M. Silver. Menorah Pub., 1988-2004) writes: “This law was stated here because Scripture deals with going out to war. Women were created only to have children. If a woman joins men in going to war she will come to engage in illicit sexual relations on the way. The law that states neither shall a man put on a woman’s garment is similar. The reason for this law is as follows. If a male who does not have a full beard mixes with women, then he and they will have sexual relations without anyone knowing. This law indicates that the custom of Israel was for the garments of men to be unlike the garments of women. There was a definite difference between the garments. This is also the practice in most countries.” Similarly see; Rashbam, Bekhor Shor, Shiruei Seforno, Abarbanel, Ralbag Beur HaMilot, Chizkuni (quote of the Ibn Ezra), and Kitzur Ba’al HaTurim on Deuteronomy 22:5.
Many sources bring both reasons, see for instance; Meor Haafela, Ki Tetze, Guide for the Perplexed, Part 3, 37, and in Sefer Hamitzvot negative commandments 39-40.There are also other explanations for the verse, for instance, people can avoid helping others by pretending they are a woman, see for instance Akedat Yitzchak, or that it is wrong to change the order of the world See Recanati on the Torah, Ki Teitzei, Rabbi David Tzvi Hoffman and seemingly Ibn Ezra on the verse, in addition see the Recanati with a cabalistic explanation regarding male reincarnation in female bodies. these explanations however, do not explain the term toevah – abomination.
3
Sefer HaChinukh 542, translated by R. Francis Nataf, Sefaria 2018.
4
The William Davidson Talmud.
5
Kessef Mishneh, Avodah Zarah 12:10, Beit Yosef, Yoreh De’ah 182:6.
6
See; Dr. Alexander Klein, Lo Yilbash: here
7
Mishneh Torah, Marriage 13:11, Trans. by Eliyahu Touger, Moznaim Publishing.
8
For more stories like this, see; Unveiling Eve, chapter 7.
9
Har Tzion Vol. 4, p. 528.
10
In Avraham min haHar on Nazir 59a such an opinion is quoted in contrast to his understanding of Maimonides. And see Ritva on Makkot 20b (see however in his commentary on Shabbat 50b and 94b, it would seem it is forbidden if it is for beautification/jewelry); the Rif (Makkot 4a), and Rosh (see the following Beit Yosef and Pilpula Charifta) hold that shaving hair in private parts is a rabbinic violation, which led some (including seemingly the Beit Yosef, Yoreh De’ah 182:6 and Maharshal, Yam Shel Shlomo, Yevamot 12, 17) to believe they rule like Tanna Kama. See also; Pilpula Charifta on Avodah Zarah 37, see also his comment on the Levush (Malbushei Yom Tov, 696), he references a similar ruling, and does not reject it. And see; Shoel uMeshiv Mahadura I, 1, 210.
Kiryat Sefer on Avodat Kochavim, 12:9, he brings both opinions, and seems to hold that with clothes, one only transgresses with intent for crossing gender spaces.
In addition, the Rashba (Chullin 64a) quotes an Itur, as well as explains the Rif to say that we only follow Rabbi Eliezer ben Yaakov unequivocally when his opinion is mentioned in a Mishnah, not when it is in a Baraita, similarly see Dina Dchaye p. 28, that there are limitations to this law, for instance many Rishonim would hold that it does not apply when Rabbi Eliezer ben Yaakov is arguing against two rabbis, so he is in the minority, similarly, if there is a ‘stam mishnah’ that agrees with the other opinion.
Since this is a Baraita, it is very possible that these rabbis would follow the opinion of tanna kama/chachamim. Especially since the Rashba (Shut, Vol. 5, 271) also maintains that shaving private areas is a rabbinic prohibition.
Also Perushim Upsakim Lerabeinu Avigdor Tzarfati, ki tetze, Pesak 462.
Also Rashbam and commentators on the chumash on Deuteronomy 22:5, including Rashi and its commentators including Mizrachi, Rabbeinu Bahya and many more.
Also many interpret Maimonides (Avodat Kochavim 12:10) this way, for instance Hagahot Maimon there, and Yam Shel Shlomo on Yevamot 12, 17, understood the rambam this way, similarly, Mikraei kodesh understands the rambam this way. The Rambam in sefer hamitzvot however also mentions the reason of avodah zarah, therefore in Avodat Hamelech (there) he explains that if someone crossdresses with intent for either, it is forbidden, but if not than permissible, and regarding this, he argues, the Rambam agrees with the Smag (that will be brought later in the article), see also Rabbi Yosef Qafih, in his Rambam, Madah, P. 564.
In the Avodat Hamelech, he mentions that the Rambam holds like the Smag, later he writes that he can’t agree with the Ritva, that is probably for this reason.There are also alternative readings of the Talmudic dispute, see for instance Shut Rabbi Yom Tov Tzahalon 56, that suggests an alternative reading of the dispute, whereby according to Rabbi Eliezer ben Yaakov it would be permissible to wear clothes, and the only thing that would be forbidden is for a woman a gun, for a man adornment.
11
Besides the sources quoted in the article see also Chizkuni, Deuteronomy 22:5.
12
Ibn Ezra on Deuteronomy 22:5, H. Norman Strickman and Arthur M. Silver. Menorah Pub., 1988-2004. And see also Chizkuni there.
13
Rabbeinu Bahya, Devarim 22:5, Torah Commentary by Rabbi Bachya ben Asher, trans. Eliyahu Munk, 1998.
14
Sifrei Devarim 226, Rabbi Shraga Silverstein.
15
See Abarbanel on Deuteronomy 22:5 that the verse also includes crossdressing for homosexual purposes.
16
Negative commandments 60.
17
The traditional interpretation is that both Tanna Kama and Rabbi Eliezer ben Yaakov require promiscuous intent, and see Binat Adam (Danzig) Responsum 74. There are others that interpret it differently, see for instance; Beit Yosef, Yoreh De’ah 182:6, Lev Sameach, Yoreh Deah 6.
18
See Pitchei Tfila Umoed, p. 485.
19
See; Jewish Encyclopedia, “MARRIAGE CEREMONIES.”
20
Unveiling Eve, chapter 8.
21
For more about Kalonymus, see; “Kalonymus ben Kalonymus.” Encyclopaedia Judaica.
22
Towards the beginning, Venice, p. 65a.
23
The Jewish encyclopedia; “TOBIAH BEN ELIJAH OF VIENNE (BURGUNDY)”.
24
See; Baalei Hatosfot (Aurbach), Vol. 1, p. 487, and footnote 35.
25
See Maharaz Binga, Machon Yerushalayim, p. 208.
26
See; Darkhei Moshe, Orach Chayim 696:5, and see gilyon rabbeinu yisrael mibruna p. 5.
27
Their opinions are mentioned in the responsum of Rabbi Juda Minz. About Rabbi Elyakim and Rabbi Gershon, see Mavo Lesefer Binyamin Zeev, Benayahu, p. 16-22.
28
Shut Mahari Minz 17.
29
In this responsum (17) he also criticizes him, however in siman 10 (Krakow, p. 18a), his criticism is harsher, this can be found there.
30
Orach Chayim 696:8, Sefaria Community Translation.
31
See for instance Banayahu, Rabbi Yosef Pardo, p. 4.
32
See; “Uziel, Isaac ben Abraham.” Encyclopaedia Judaica.
33
See the responsums of the responding rabbis, and see Pitchei Tfila Umoed, p. 494, footnote 32, 33.
34
See; “Alegre, Abraham ben Solomon.” Encyclopaedia Judaica.
35
Lev Sameach, Yoreh Deah 6.
36
See; “Benveniste, Joshua Raphael ben Israel.” Encyclopaedia Judaica. And see Sha’ar Yehoshu’a, Choshen Mishpat, 11 (Machon Yerushalayim, 50b).
37
See Sha’ar Yehoshu’a, Yoreh Deah 5.
38
See Kitvei Rabbi Yehuda Arye Mimodna, 154. And see Otzar Yisrael, Vol. 6, Rabbi Simone Luzzatto, “Luzzato, Simchah ben Yitzchak.”
39
Achronim that follow this, the Levush; Ateret Zahav, 182, Levush Hatchelet 17, 2, and Levush Hachur 696, 8, see also the commentators there, like the Hagahot Maharo Azulai (695:7), and see also Elya Rabba (696:15) that he writes that in a place where this is the custom they should not change it relying on the Rema. See also Beer Moshe Vol. 8, 7 (and end of 8), Hisorerus Teshuva, Vol. 3, 500, Avnei Zikaron (Rabbi Alter Shaul Pfeffer) Vol. 3, 39, p. 82a, Mekor Chayim of Rabbi Chaim David Halevi, Vol. 4, p. 364. And see Avnei Derech, Vol. 17, p. 388, and Rabbi Ben Zion Abba Shaul (Dvar Emet Vol. 1, beginning) ruled this to be the ashkenazi verdict, and therefore allowed it for sefardi kids. And see also Diglei Hodaya VehaMitzva (Landau), mitzvah 70, p. 64, though he does bless those that are stringent, and Yemei Yosef, Vol. 2, Yoreh Deah 6.
We also find sources that write that the Torah only forbade dressing that leads to ‘toevah’ – illicit sexual conduct, see for instance commentators on Deuteronomy 22:5, like Rashi, Bahya, Bartenura and moreת and see also, Perushim Upsakim Lerabeinu Avigdor Tzarfati, ki tetze, Pesak 462.
It would also seem like this from Midrash Lekach Tov on the verse, and others.
Similarly Rabbi Abraham Abba Schiff in To’afot Re’em would seem to support this on the Yereim 385-6, in footnote 5.
And see earlier in footnote 10.
There are also rabbis that oppose this ruling but seem to accept it to some degree, see for instance olelot efrayim maamar 309. See also Chemdat Yamim, Vol. 2 (Bnei Brak), p. 179. And see also Turei Zahav, Yoreh De’ah 182:4, and Be’er HaGolah, Yoreh De’ah 182:7, that they seems to accept it to some degree and reject it partially for other considerations, I however would argue that they believe it is forbidden rabbinically.
40
See; “Apt Hasidic Dynasty.” YIVO Encyclopedia of Jews in Eastern Europe.
41
Esther 9:1, JPS, 1985.
42
Rabbi Shelomoh ha-Kohen Rabinowicz, in his Tif’eret Shelomoh (Moadim, Warsaw, p. 96c), also discusses this custom in light of mystical interpretation.
43
Similarly if the goal is not for beautification many permit it, see for instance, Sridei Eish, Yoreh Deah 41. However that might not apply here since his intent while dressing and putting on the jewelry is partially to look prettier, even if that is not the ultimate desire.
44
This ruling would result from the reasoning of Rabbi Joseph Karo, mentioned earlier, and all those that agree with his analysis of the Talmud.
The Pri Megadim on Orach Chayim, Mishbezot Zahav 696:5, and for more see Yalkut Yosef, Purim 965. And see Igrot Kodesh Vol. 10, p. 255.
Similarly, in the introduction to the book Maase Rokeach on the Rambam, Rabbi Abraham ben Moses ben Maimon, is quoted as saying so. It is also a bit implied so from the Yereim 385-6 where he writes that the prohibition applies even if done as a joke (see however To’afot Re’em there, footnote 5).
45
See; Turei Zahav, Yoreh De’ah 182:4 (and see what he wrote on Rashi in Yad David Deuteronomy 22:5), and Be’er HaGolah, Yoreh De’ah 182:7, and Shut Rabbi Akiva Yosef Schlesinger, Yoreh Deah Vol. 2, 85 (see however what he wrote in Beit Yosef Chadash (Jerusalem), p. 83d). And see Kedoshim Tihyu, p. 347.
46
See for instance Beer Moshe Vol. 8, 7.
47
For more, see; “Ḥagiz, Moses.” Encyclopaedia Judaica.
48
For more, see; “Horowitz, Isaiah ben Abraham Ha-Levi.” Encyclopaedia Judaica.
49
For more, see; “Epstein, Jehiel Michal ben Aaron Isaac Ha-Levi.” Encyclopaedia Judaica.
50
See Hisorerus Teshuva, Vol. 3, 500.
51
Shabbat 94b (and Makkot 20b) The William Davidson Talmud (Koren – Steinsaltz).
52
See Beit Yosef, Yoreh De’ah 182:9, see however Shoel uMeshiv Mahadura I 1:210, he seems to think that from most poskim it would seem to be rabbinic.
53
Yoreh Deah 182. Regarding shaving private areas, and whether it is rabbinic, see Beit Yosef, Yoreh De’ah 182:6, see however Tzemach Tzedek, Yoreh Deah, 93.
54
See for instance Tosefta Avodah Zarah 3; it is forbidden to look in a mirror if one is getting a haircut from a Kuti.
55
Tosefta Avodah Zarah 3, Jerusalem Talmud; Avodah Zarah 2:2 and Shabbat 6:1, and see Shulkhan Aruch, Yoreh Deah 156:2.
56
Bach, Yoreh De’ah 182:5.
57
See for instance Sha’ar Yehoshu’a, Yoreh Deah 5, that it is only forbidden to shave private areas biblically, because it leads to natural consequences which lead to promiscuity, while this does not apply to armpit hairs, the two are put together. The reason it is forbidden rabbinically according to Tanna Kama, is because it is not clothes. Similarly the Smag who holds it is biblical, would seemingly argue that the prohibition applies only if there is intent for sexual gain, like being prettier, or fitting in better in women’s spaces, which could apply to shaving. It is also very possible that the rabbinic prohibition only applies to hair and mirrors.
58
There are many rabbis who maintain that even wearing a men’s coat to avoid rain is forbidden (See; Yad Haktana, Madah, p. 222b. And see; Siftei Kohen, Yoreh De’ah 182:7, if the person looks like the other gender, it would still be forbidden even according to the Bach.). And some who apply this even to when at home alone (See for instance Teshuvot Vehanhagot Vol. 1, 456.), while as mentioned above, many rabbis maintain that if it is for an alternative purpose it would be permissible, Rabbi Joel Sirkis’s argument does not directly contradict those opinions, as they were discussing costumes which is about clothes, but not about adornment.

It should also be mentioned that some rabbis accept the premise of the Rema regarding clothes, but believe adornment like jewelry is forbidden biblically even without promiscuous intent, see Haemek Davar on Deuteronomy 22:5.
59
Shulchan Arukh, Orach Chayim 656, Sefaria Community Translation.
60
See for instance; Avnei Nezer, Even Haezer Vol. 1, 1:8. And see also in his responsum in Yoreh Deah 321, regarding someone’s child having a defect, and that is more than a great loss.
61
See for instance; Igrot Moshe, Even Haezer Vol. 4, 32:4.
62
In Igrot Moshe, Orach Chaim Vol. 1, 172.
63
See for instance Zera Emet, Vol. 3, p. 40b, Svhut Yaakov, Vol. 1, 98, Kavod Melachim (Landau) from p. 11, Shut Haramatz Vol. 1, Orach Chaim 18. And see; Yabia Omer Vol. 4, Even Haezer 3, that even for a sin which is neither an asei nor a lav it might apply.
64
See, Aderet; Over Orach, p. 207; and Kavod Melachim (Landau) p. 11.
In addition, see Pitchei Tshuva and Rabbi Akiva Eger on the beginning of Yoreh Deah 157 that there are authorities that believe that for mitzvot which don’t have malkut punishment, one does not need to spend all his money to not transgress. The knesset hagdola (Orach Chaim 695) writes (arguing with the ruling of the Rema), that even the Smag would forbid it, and only requires intent for promiscuity for the punishment, lashes. Following this, it could be argued that one does not need to incur a significant loss for this prohibition if done without intent for promiscuity.
65
It would seem that the combination of both makes it lighter, see for instance; Nimukei Yosef on Bava Batra 44b quoting the Rashba; Beit Yosef, Magen Avraham Orach Chayim 276; Knesset Hagdola, Yoreh Deah 102, (Saloniki) p. 122a, and many more.
66
It would seem that crossdressing is considered a “lav sheeno shave bakol”, a prohibition that only applies to some. The reason for this would be that the Maimonides (Negative Commandments 39, 40), Chinukh (542, 543) and Rasag (Negative Commandments 132, 133) count them as two separate commandments in the mitzvah count. See the Chinukh in mitzvah 543: “And this prohibition is practiced in every place and at all times by males.” The exception is Sefer Mitzvot Katan (33) who only counts it as one, and see Rabbi Yerucham Fishel Perla on the Rasag.
And see Shoel uMeshiv Mahadura I, 1, 210, while his argument from rashi is not conclusive, he seems to hold that slaves are not obligated in this prohibition, and in Even Yekara Vol. 3, 93 he makes this point and explains that it is since women are not commanded in the sin of beautification, since they are different commandments for men and women.
There are however those that argue that a slave is commanded in this prohibition, that does not necessarily negate the point.
Slaves are not allowed to shave their head even though women may, since the reason women are not included in the prohibition is because they don’t have beards, therefore a slave who does is, the Rambam writes in Avoda Zarah 12:2:
“A woman is exempt if she shaves the head of a man or has her own head shaven. [Since Leviticus 19:27] states: “Do not cut off the corners of your heads and do not destroy the corners of your beards,” [an association between the two prohibitions is established]. Whoever is liable for shaving is liable for cutting off the corners. Therefore, because women are not liable for shaving – since they do not have beards – they are not liable for cutting off the corners [of their heads]. Accordingly, slaves are forbidden to cut off the corners of their heads, since they do possess beards.”
And nonetheless it is considered “eino shava bakol”. (see Yevamot 5a)
The argument could be made that this is why a slave is obligated in the prohibition of crossdressing, see Yabiah Omer Vol. 8, 54:11, and see Machane Chaim, Vol. 2, Yoreh Deah 30, and Tal Torah (Rabbi Meir Arik), on Bava Metziah 60a. And see; Minchat Elazar Vol. 4, 23; and Sridei Eish, Vol. 2 Yoreh Deah 41.
There is however an argument to be made that slaves are prohibited from crossdressing as the sin of women and men is essentially the same prohibition, it would seem this way from for the Minchat Chinukh 543, and see also the above mentioned in Minchat Elazar (Vol. 4, 23), and Sridei Eish (Vol. 2 Yoreh Deah 41). This however does not necessarily negate the point either, see Yabia Omer quotes above, in addition see also Avnei Zikaron (Rabbi Alter Shaul Pfeffer) Vol. 3, 39, p. 80b.
In addition see Rash MiShantz and Melekhet Shelomoh on Mishnah Bikkurim 4:2, and Avraham Min Hahar on Yevamot 83a.
I saw that in Kedoshim Tihiyu p. 531 he rejected this point, however I am not convinced by his argument.
67
See Pitchei Tshuva and Rabbi Akiva Eger on the beginning of Yoreh Deah 157.
68
Pub. Kehot Publication Society, Trans. by Rabbi Eliyahu Touger and Uri Kaploun.
69
See Magen Avraham 13:8.

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