To Donate Click Here

The Price Tag for Jewish Outreach


Rashi in this week’s parasha teaches that Yaakov Avinu was punished for actively preventing Dina from marrying Eisav, hence denying him the opportunity to repent. Would it have been permissible for Yaakov to allow his daughter to marry Eisav just to offer him the opportunity to repent? What was demanded of Yaakov, and why was he punished? Why was Leah rewarded for not marrying Eisav, while her daughter — punished? And practically – should Jewish outreach come at the price of one’s own spiritual danger? When is the price too high to pay? Children and adults may find themselves in a negative surrounding. What can a parent do for his child in this situation and what should an adult do? Of this, and more in the following article.

Disappearing Dina

When the Torah describes Yaakov’s meeting with Eisav, it lists each person present – Yaakov’s eleven children and four wives. The only one missing from the meeting was Dina. Rashi (Bereshis 32:23) quotes a Midrash (Bereshis Raba 80:4) telling us that Yaakov, in preparation for the meeting, was afraid Dina would appeal to Eisav and he would demand her hand in marriage. Therefore, Yaakov locked her in a box to ensure he wouldn’t see her.

Yaakov’s Punishment

Rashi adds that this was the reason Dina was abducted by Shechem – as a punishment for denying his brother the opportunity to repent. How could that be possible? Was Yaakov obligated to offer his daughter to any Tom, Dick, and Harry so she might flip him around? Was there no danger of her learning bad behavior from them?

The Chida (Chomat Anach, Vayishlach 7) asks why Leah is lauded and rewarded for praying not to marry Eisav – if it was a negative thing, she should have been punished herself for refusing to marry him?

The question becomes even more pointed when reading Chazal’s instructions which indicate the exact opposite. The Gemara (Psachim 49b) writes that one who gives his daughter away in marriage to an ignoramus fellow (am ha’aretz) is equated to having tied her up and placed her before a lion. In another source we find that Yosef was rewarded for standing on his tiptoes to protect his mother from Eisav’s gaze. So what was the issue here?

Kiruv – With a Price

Herein lies one of the most difficult questions in the field of kiruv, Jewish outreach – what is the price one is obligated to pay in order to teach estranged Jews about their heritage? Do we do anything to bring others back, or must our first obligation be to maintain that which we already have?

A case in point: One of the great leaders of the previous generation opened an institution attempting to combine both.  The result was a two-way road — on the one hand it taught Judaism to many unaffiliated Jews who had, until then, been ignorant about their heritage, but on the other hand, many good religious Jews found it detrimental to their spiritual health. The rabbi called his institution a “Red Heifer” or para aduma, which renders the impure – pure, and the pure – impure.

When is the price worth paying and when is it just too high? Every case needs to be judged individually. There’s no one answer fits all here,  but through close scrutiny of the various commentaries on the story of Dina we can attempt to highlight some relevant issues.

Improper Intention

Rabbenu Ovadia of Bartenura in his commentary on Rashi (Amar Nakai, Bereshis 32:53) asks this question and answers that preventing Dina from marrying Eisav was certainly praiseworthy and necessary. The only demand of Yaakov Avinu was for a subconscious thought that Yaakov really didn’t want Eisav to repent. He was afraid that should she marry Eisav she would change him for the better.

The reason he might have entertained such a notion is because if Eisav were to repent, the following portion of his father’s blessings would not be realized: (Bereshis 27:29) “Nations shall serve you and kingdoms shall bow down to you; you shall be a master over your brothers, and your mother’s sons shall bow down to you. Those who curse you shall be cursed, and those who bless you shall be blessed.” This part depended upon Yaakov’s righteousness and Eisav’s wickedness, as the Gemara writes (Megillah 6a): “If someone says to you that both cities (Caesarea and Jerusalem, representing Eisav and Yaakov, respectively) are destroyed, do not believe him. Similarly, if he says to you that they are both settled in tranquillity, do not believe him. If, however, he says to you that Caesarea is destroyed and Jerusalem is settled, or that Jerusalem is destroyed and Caesarea is settled, believe him. As it is stated: “Because Tyre has said against Jerusalem: Aha, the gates of the people have been broken; she is turned to me; I shall be filled with her that is laid waste” (Ezekiel 26:2), and Tyre, like Caesarea, represents Rome. The two cities cannot coexist. Rav Nacḥman bar Yitzhak said: The same idea may be derived from here: “And the one people shall be stronger than the other people” (Bereshis 25:23), teaching that when one nation rises, the other necessarily falls.”

Yaakov Avinu, who was a perfect person in every way, hid Dina so she should not be taken as wife to Eisav. But for the subconscious thought that he didn’t want Eisav to repent so the blessing should not be passed to him, he was punished.

Don’t Slam the Door

The Alter of Kelm was known to say that while Yaakov acted properly in hiding Dina in the box, when locking her in he should have done so with a measure of heartache, regretting having to do so. He should have locked the box with a sigh and prayer that Eisav repent. Perhaps, the Alter meant to say the same thing as Rabbenu Ovadia.

The Ramchal (Mesials Yeshairim, chapter 4) lists several actions for which those who reached a level of perfection are chastised. One of the items on the list is Yaakov Avinu having locked away Dina. While he surely meant well in preventing the marriage, since a slight thought of personal gain was also involved, he was punished for it.

Bad Friends

This idea can have real life consequences. One may be blessed with an emotionally strong child with great leadership qualities who finds himself attracting weaker elements in his social circle. While he could perhaps teach his friends good things — lead them to chessed and Torah projects — since he is just a child, we must do everything to end that relationship. Even though it may seem, for a while, that the good child has the upper hand and is influencing others positively, we must do everything to protect our child from bad influences, even if that nails a coffin on the possibility of him changing his friends. Here, we must take Ya’akov Avinu’s lesson to heart and in doing so, pray for the other children, and really feel bad for them. While our child may have been capable of changing them, the risk to our own child’s spirituality is too high to take.

Eisav Would Have Repented

Rashi writes that Yaakov was punished because perhaps Dina would cause him to repent, but the Midrash (Sechel Tov, Vayishlach 34:31) writes that she certainly would have made him turn around. Yalkut Shimoni take a similar stance (Iyov 900): “Had Dina married Eisav she would have converted him just as she converted Iyov.” Since Dina eventually married Iyov and converted him because she had those capacities, she could have done the same for Eisav.

Thus, we have a second approach why Yaakov was punished. According to these midrashim, Yaakov, who was her father, knew her capabilities and was punished for denying his brother the opportunity.

The Or Hachaim (Bereshis 27:1) deduces from this Rashi that there were sufficient grounds to assume that, based on Dina’s abilities, she would, indeed, have caused Eisav to repent. This was why Yitzchak wanted to give him the blessings – so it would serve as a catalyst for positive change.

While our perception of Eisav is certainly negative, the pasuk in Ovadia (1:6) tells us his wickedness was indiscernible to the eye: “How Eisav was searched out, how his hidden things were revealed!” His evilness was only clear to G-d Who knows what is hidden in the heart, but to humans he didn’t necessarily seem evil at all.

While Eisav’s sins were indicative of his evilness, nevertheless, he was very close to repenting, and had Dina married him, chances are very good that he would have changed for the better.

Rabbi Moshe Amarillo (Yad Moshe, Vayechi) explains the difference between Leah, who is praised for praying not to marry Eisav, and Dina – for whom Yaakov was punished for not allowing Eisav to marry. While Leah was a righteous woman, her father was wicked. Had she married Eisav she would have placed herself in spiritual danger under Eisav’s influence. But Dina, who was raised in Yaakov’s house, in addition to her and Eisav’s holy forefathers, might have indeed changed Eisav.

Here we can learn that one outreach attempt cannot lay the rule for other opportunities. Every situation must be judged individually – at times the possibility of making a difference is almost ensured, and at others – close to impossible. Where the potential for change is lower than the potential for negative influence, with all the heartache, we must never endanger our own spirituality for another’s growth.

Different People – Different Missions

The Chida (Chomat Anach, Vayishlach 7) similarly explains that according to the hidden Torah (kabbala) Dina’s mission in the world was to reveal the good that was concealed in an evil person. He writes extensively on the topic and explains how it was actualized with Shechem. While the topic cannot be covered properly in this forum, one point is clear – Yaakov, in his wisdom should have known that this was his daughter’s mission in the world. For preventing it, he was punished.

If there is a lesson here to take home, it is this: when a Torah leader sends a choice individual on a specific outreach mission, his chances of succeeding are very high despite apparent spiritual danger. Another person, however, may not be successful because it is not his mission. Instead, he may end up learning negative behaviours.

There is, however, another important message here. A times, we may find ourselves, due to extraneous reasons, in a situation which has the potential to harm our spirituality. Here we must remember that if Hashem placed us in this situation it must be our mission in the world, and we can make a change. Let us remember why Yaakov was punished for not allowing Dina to marry Eisav and be open to accept our calling when it presents itself.


Even if we don’t do outreach in order to protect ourselves from detrimental influences, we must be sure no other motives infiltrate our decision, be it motives of honour, social status, or simple laziness. Such a decision must be done with heavy-heartedness. If a parent must convince his child to break up a relationship on spiritual grounds it must be done with a prayer for the other child and after making every attempt to help him reach safe ground.

We must also remember that no two situations are alike – some have a lot of potential and a small risk while others have greater risk and slighter potential. Every situation warrants a question to Torah authorities as to the correct way to proceed.

We must remember that every person has his mission in the world, and even if we initially try to avoid doing outreach because it may endanger our spirituality, if we find ourselves placed in such a situation it was Hashem Who placed us there and we must do everything we can to glorify Hashem’s Name. This itself will help to save oneself from negative consequences.

Leave a comment

Your email address will not be published. Required fields are marked *