First of all, one must know, with all the gravity of sexual transgression, penitence (t’shuva) is certainly possible, as the Rambam states: “There is nothing that stands in the way of repentance” (Laws of T’shuva, 3:24).


“Here I want to awaken you to a painful and shocking matter about which many people err. There are many people who refrain from speaking about these things under the pretext of modesty. May Heaven help us! In such a fallen and licentious generation as ours, where everything is exposed without shame in the open – to speak about holiness and modesty – this is considered an affront to modesty?! Can there be a greater deception on the part of the evil inclination than this?! On the contrary, it is an absolute obligation to speak about these matters in public!”

The Torah giant, Rabbi Aharon Cutler, of blessed memory.


by Tzvi Fishman


Shmirat HaBrit means guarding the Brit or Covenant. While our connection to G-d, and to Eretz Yisrael (the Land of Israel), are eternal, the Torah warns our forefather, Avraham, that Shmirat HaBrit (guarding the Covenant) is of paramount importance in insuring that the Covenant between G-d and the Nation of Israel remains constantly active:

And I will give to thee, and to thy seed after thee, the land in which thou dost sojourn, all the land of Canaan, for an everlasting possession, and I will be their G-d. And G-d said to Avraham, therefore you shall safeguard My Brit, you and your seed after you in their generations. This is My Brit that you shall safeguard, between Me and you, and your seed after you, every male among you shall be circumcised” (Bereshit, 17:8-10).

The meaning of Shmirat HaBrit, as the Zohar stresses, is not merely the obligation to circumcise our children, but also to guard our sexual purity. This includes all forbidden sexual acts including the spilling of semen in vain. This holiness is what differentiates us from the gentile nations, and this is what guarantees our settlement of Eretz Yisrael.


Throughout the generations oue Sages have emphasized that sexual purity is one of the most important foundations of Am Yisrael.  The Torah itself warns us that sexual transgression leads to exile from our Land (Vayikra, 18:28).

The holy Zohar states:

Rabbi Abba explained the verse: “The secret of Hashem is revealed to those who fear Him, to make known to them His Brit” (Tehillim, 25:14). “The secret of Hashem” is the most exalted secret of the Torah that G-d only grants to those who fear sin. To those who fear sin, G-d reveals the most exalted secret of the Torah. And what is the most exalted secret of the Torah? It is (the secret of) the sign of the holy Brit, which is called the secret of Hashem – this is the holy Brit. (Zohar, Bereshit 236b)

The Baal HaTanya explains that while all transgressions blemish the spiritual channel that brings Divine blessing to the world, sexual transgressions cause the most damage (Igeret HaT’shuva, Ch.6). This is true for single and married people alike.

Unfortunately, the in-depth study of this subject, a vital  foundation of Am Yisrael, has been left largely unlearned. This is due to two factors: the long tradition of modesty surrounding the subject; and the fact that the texts which elaborate on the importance of Shmirat HaBrit belong, in large measure, to the world of Kabbalah and to the secrets of Torah.

The works of Rabbi Nachman of Breslov are most known for their focus on Shmirat HaBrit. However, the vital role of Shmirat HaBrit is not only found in Hasidic literature and in the secrets of Torah. As we shall discover, the theme appears again and again in the Torah, the Talmud, and in the precise, down-to-earth details of Jewish Law.

The great Torah scholar, the Gaon of Vilna, also known as the Gra, throughout his commentaries on the “Zohar” and “Tikunei HaZohar,” also emphasizes the role of Shmirat HaBrit as the foundation of Jewish life. For instance, the Gaon of Vilna writes that “Tikun HaBrit” (rectifying blemishes to the Brit) is the ultimate purpose of man (Tikunei HaZohar, Tikun 23, Folio 76, Column 3). He states that Shmirat HaBrit is the key to understanding the secrets of Torah (Zohar, Parshat Pikude, 248a).  And he notes that the Redemption of the Jewish people from the exile will come speedily – if the Jewish People merit it due to Shmirat HaBrit (Tikunei Zohar, Tikun 21, Folio 56, column 3).

Furthermore, the holy Zohar emphasizes repeatedly that the spiritual and material redemption of the Nation of Israel, and of the world, is dependent on Shmirat HaBrit. Therefore, the more we sanctify ourselves, the more we will be able to strengthen our connection to Eretz Yisrael, not just for ourselves, but for the Jewish nation as a whole.

Our Sages also teach us that the holiness of a Jew is dependent on the degree to which he guards his eyes from looking at forbidden images. Needless to say in today’s “everything goes” society and with easy access to the Internet, the test is not an easy one. Without some type of foolproof filter, a smartphone and home computer can become great obstacles to purity. HaRav Shmuel Eliahu, the Chief Rabbi of Tzfat, has even written a prayer to be recited before a session of Internet viewing to guard a person from sin.

So grave is the danger of Internet watching that Torah authorities have ruled that Internet surfing without a reliable filter can lead to a list of Torah violations including: “Thou shall not put a stumbling block in front of a blind man.” Others are:

“You shall be holy, for I the L-rd your G-d am holy!”(Vayikra 19:2)

“Thou shall not turn astray after your hearts and after your eyes which lead you astray.” (Bamidbar 15:39)

“Therefore shall your camp be holy, that He see no unclean thing in you and turn away from you.”(Devarim 23:15)

“And you shall guard yourself from every evil thing.”(Devarim 23:10)

“Do not turn astray after their gods!”(Vayikra 19:4)

“You shall not walk in the customs of the gentile.”(Vayikra 20:23)

“Thou shall not bring an abomination into your house.”(Devarim 7:26)


Tefilla Zaka

On the eve of Yom Kippur, to enter into a mood of repentance, many congregations recite the prayer called “Tefilla Zaka,” which begins:

“Almighty, Father of mercy and forgiveness, Whose right hand is extended to accept those who return in repentance, and Who created man to bestow goodness upon him at the end of his days, and Who created in him two inclinations, the good and the evil inclination…. “And now, my L-rd, I didn’t listen to Your voice, and I followed after the counsel of the evil inclination…and not only did I not sanctify my organs and limbs, but I made them impure. You created in me a brain and a heart, and fashioned in them the faculty of thought to think good thoughts and pure contemplations, and a heart to understand your holy words, and to pray and pronounce every blessing with pure intentions. And I made them impure with sordid thoughts and unholy contemplations. And worse than this, through my evil fantasies and foreign thoughts, I came to emit semen in vain, both by accident and knowingly, through impure seminal emissions that make the whole body impure.”



The Torah warns us that Israel’s success and security is dependent on guarding our holiness, specifically in the area of sexual purity:

When you go out to encamp against your enemies, then guard yourself from every evil thing. If there be among you any man that is not clean by reason of an impure emission of semen at night, then he shall go abroad outside of the camp, he shall not come within the camp” (Devarim, 23:10-11).

For the L-rd your G-d walks in the midst of thy camp, to deliver you, and to give up your enemies before you; therefore shall your camp be holy, that He see no unclean thing in you and turn away from you” (Devarim, 23:15).

This demand for sexual purity applies not only to the soldiers of Israel, but also to community life in general. The Torah commands us, “You shall be holy, for I the L-rd your G-d am holy” (Vayikra, 19:2).

On a national level, our ability to conquer and settle all of the Biblical borders of the Land of Israel, depends on the holiness with which we lead our lives, both for soldiers in the Israeli army, and civilians in their private lives. This is a great key to victory. By guarding our holiness, the Shechinah (Divine Presence) stays with us, fighting our battles alongside our soldiers and tanks.

For the L-rd your G-d walks in the midst of thy camp, to deliver you, and to give up your enemies before you; therefore shall your camp be holy….”

To ensure the day-to-day holiness of the Jewish People, the Torah and its Sages set forth guidelines to prevent a man from succumbing to the temptations that can easily cause him to err.

In addition to the prohibition of gazing at erotic images, Jewish Law demands that a man exert special care to distance himself from unnecessary interaction with women (Shulchan Aruch, Even HaEzer, 21:1). This warning is not because women are evil, G-d forbid. Rather, it comes to guard a man from falling into transgression.

Regarding the prohibition against being alone with a woman, Jewish Law states:

“One must not be alone with any woman, whether she is young or old, a Jew or non-Jew, a relative or not, except in the case of a father with his daughter, a mother with her son, and a husband with his wife” (Kitzur Shulchan Aruch, 152:1).



It is important to note that all unmarried women are considered to be in a state of menstrual impurity. The impurity of “niddah” (menstrual impurity) is one of the severest forms of spiritual uncleanness. The punishment for having relations with a woman considered niddah is “karet,” dying before one’s time. Because of the great strength of niddah impurity, a man does not only become impure through having sexual relations with her, but also through intimacies like hugging and kissing.

When a man pollutes himself through sexual transgression the Shechinah (Divine Presence) departs from him. Holiness and impurity cannot exist in the same place. The Midrash teaches that the Holy One Blessed Be He is slow to anger in regard to every sin, except immorality (Bereshit Rabbah 26). “



Not only is physical contact with women prohibited, gazing at them to enjoy their beauty is also a serious Torah transgression (Shulchan Aruch, Even HaEzer, Ch. 300, Section 100:2).

Regarding the Torah commandment, “You shall not go astray after your hearts and after your eyes” (Bamidbar 15:39), the Talmud explains: “After your hearts – this refers to idol worship. After your eyes – this refers to sexual immorality” (Berachot 12B). The eye and the heart are the two instruments of sin. The eye sees, the heart desires, and the body completes the action (Rashi on Bamidbar 25:39).

Today, because of the promiscuity and immodesty that pervade modern life and Western culture, we have become accustomed to this state of affairs, as if this is the natural way to be. However, Jewish Law demands a higher level of moral behavior.

“Whoever gazes at a woman forbidden to him, and says to himself that there is nothing wrong with this, for he hasn’t had sexual relations with her, or even touched her, he is mistaken. Gazing at women is a serious wrongdoing, for it brings a man to sexual transgression, as it says, “You shall not go astray after your hearts and after your eyes” (Hilchot T’shuva of the Rambam, 4:4).

The Gemara teaches: “You should guard yourself from every evil thing – this means a man should not gaze upon an attractive woman, even a single one, nor upon a married woman, even if she is ugly” (Avodah Zara 20A). This is because, “A man shouldn’t have sexual thoughts in the day and come to seminal impurity at night” (Avodah Zara 20B).

In summary, we can see from the warnings of the Torah, from the admonishments of the Talmud, from the exacting prohibitions of Jewish Law, and from the inner understandings of the Zohar and the Kabbalah, that Shmirat HaBrit is indeed the foundation upon which all of life is based.



In the light of these mystical insights, we can understand the great importance of the laws of modesty for women. The women of Israel have the responsibility to dress in a modest fashion, so as not to cause Jewish men to be drawn into sexual fantasies and sin. Their attire should cover the body according to Jewish Law. For example, sleeves should extend lower than the elbow. Skirts should extend below the knees. Clothes should not be so tight-fitting that they expose her figure in a suggestive fashion. When a woman dresses immodestly, she arouses the sexual urge in the men who see her, and this can cause sexual fantasies and the subsequent spilling of semen in vain. Besides violating the laws of modesty, women who dress in an enticing fashion transgress the prohibition of putting a stumbling block in front of a blind man, in that they lead others to sin.

In order to maintain a healthy, wholesome society, it is incumbent upon a woman to carefully guard her beauty from the public eye, and reserve its powerful effects for the enhancement of a romantic, loving relationship with her husband only.



The reader can rightfully ask, “After all that I have learned about Shmirat HaBrit, what can I do to rectify my past mistakes?”

First of all, one must know, with all the gravity of sexual transgression, penitence (t’shuva) is certainly possible, as the Rambam states: “There is nothing that stands in the way of repentance” (Laws of T’shuva, 3:24).

Furthermore, a person should not think that because of the great number, or because of the seriousness of his sins, he can never start anew. This is not true, as the Rambam makes clear:

“Let not the penitent suppose that he is prevented from attaining the degree of the righteous because of the iniquities and sins that he has committed. This is not so. He is beloved by the Creator, and desired by Him, as if he had never sinned. Moreover his reward is great, since through having tasted sin, he renounced it and overcame his evil passions. The Sages say, ‘Where penitents stand, the completely righteous cannot stand’ (Berachot 34B). This means that the degree attained by penitents is higher than that of those who had never sinned, since the penitent has had to put forth a greater effort to subdue his passion than he who has never sinned” (Ibid., 7:4).

The Talmud teaches that the penitent not only cleanses himself of transgressions, his penitence brings blessing to all of existence. “Great is penitence for it brings healing to the world, and an individual who repents is forgiven, and the whole world is forgiven with him” (Yoma 86A).

The spiritual renewal awakened by t’shuva is undoubtedly one of the most uplifting experiences in life. Nonetheless, because of the pain involved in facing past errors, and the need to make real changes to set one’s life on a healthier path, the challenges facing the penitent are great. This is especially true when it comes to redressing sexual transgression since the penitent is called upon to redirect life’s most powerful urge from an egotistical quest for personal pleasure to a fervent love and attachment to G-d.

The essentials of repentance are that a person abandon his transgression, remove it from his thoughts, regret his past action and resolve never to do it again. He must make an oral confession, verbalizing the resolutions he made in his heart. Moreover, it is necessary to specify the sin (Rambam, Laws of T’shuva, 2:3).

In starting off on the road of t’shuva, the penitent has already succeeded. For in reaching out to G-d, he has already attached himself to the true meaning and greatest pleasure of life.


There is a Tikun!

 Our Sages have set forth guidelines on how to rectify the damages of sexual transgressions. First and foremost is increasing the study of Torah. If a person was accustomed to learning one chapter a day, he should now learn two; or if he learned one page, let him now learn two (Shulchan Aruch, Orach Chaim 615; Mishna Berura, sub-section 3). Just as immersion in a natural spring purifies, so too does immersion in the Torah.

The Baale HaTanya writes: “Since the violation of the Covenant through wasteful emission, to say nothing of stark immorality and unions prohibited by the Torah and Sages (for the words of the Sages are more grave) causes a blemish in the mind, therefore the rectification is to occupy oneself with Torah which derives from Wisdom” (Igeret HaT’shuva, Ch.9).

There are additional things that aid in rectifying blemishes to the Brit, like immersion in a mikvah, confessional prayers, guarding over one’s eyes, doing extra deeds of kindness, and giving charity as generously as one can. Since feelings of loneliness and depression can lead people into sexual transgression, an important remedy to be happy as Rebbe Nachman taught: “It is a mitzvah to be always happy.”

No room for depression or despair.

Although sexual transgression is a major wrongdoing, a person must feel happy and confident knowing that once he sets out on the path of tikun, Hashem is immediately present to assist his efforts and cleanse him of sin. Depression and despair are the counsel of the evil inclination. The penitent must turn his back on them and find joy in the loving embrace which Hashem extends to all penitents. Even if you fall backwards again and again, know that setbacks are a part of the journey. Indeed, the Baal HaTanya notes that some people are tested over and over in this process of cleansing and that the battle to overcome one’s evil inclination has a tremendously positive influence on all spiritual worlds effecting tikunim even greater than those of the holy Tzaddikim who are not tested in this crucible of passion.


In order to assist the penitent in his path of rectification, masters of the Kabbalah composed special prayers called “Tikunim” which have the power to erase the blemishes caused by sexual transgressions. Perhaps the most known Tikun is the “Tikun HaClalli” of Rabbi Nachman of Breslov.  The “Tikun Hatzot,” the midnight lament over the destruction of Jerusalem, and the special tikunim during the period of “Shovavim,” are also recommended by Kabbalists.




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