Vayishlach

Thirty four years after leaving home, Yaakov is now on his way back.   Despite those years, Eisav's feelings haven't calmed and he is heading toward Yaakov with his army to settle the score.  In an effort to win him over, Yaakov then sends a massive gift. The posuk then tells us ויקח את שתי נשיו ואת שתי שפתיו ואת אחד עשר ילדיו, he took his two wives, his two handmaids, and his eleven sons and crossed the river Jabbok. 

Rashi explains that the reason that the number eleven was specified & not just  את ילדיו which would have then meant all his children, was to tell us that Dina was missing. Where was she? Rashi tells us that Yaakov hid her in a box so that Eisav wouldn't see her & want to marry her.

However, Rashi continues & says that Dina was captured by Shechem as punishment for Yaakov hiding her from Eisav.  Perhaps, if he had married her, she would have helped him change his ways.  

‎The question posed by many commentators as well as by רב אברהם יצחק סורוצקין is why was Yaakov punished since he was merely using common sense.  If Eisav, while living in the house of Yitzchok & Rivka, wasn’t influenced to change his ways, how would marrying this little girl influence him to change?

The gemara in Sanhedrin explains the reason why the prophecies of the destruction of אדום in the future were said by עובדיה.  עובדיה, who was raised by two wicked people & wasn’t influenced by them was chosen to prophecize on the downfall of Eisav, who was raised by two Tzadikim & didn't learn from their ways. This informs us that normally one who was raised by two Tzadikim should have been influenced by them; if he wasn't, then how could we expect that Dina would be able to influence him? 

He answers by bringing the Midrash Rabba that tells a story of two very pious people that were married to each other. For many years they had no children. One day, they turned to each other and said that for us to remain together without children isn't doing anything for Hashem. Let's divorce; maybe with other people we'll have children that will grow to serve Hashem. 

So, with heavy hearts they divorced & found other mates.  Unfortunately, they didn't do so well with their new mates who were way below their standard of piety. 
Interestingly enough, the pious man who married beneath him was slowly dragged down to her level while the pious woman who married beneath her, brought her husband up to her level. The Midrash tell us that this teaches us that spirituality comes from the woman. 

There is a special power that a woman has to influence her husband, whether for bad or for good.  As the posuk says, אעשה לו עזר כנגדו I will make him a helper against him.  Rashi explains if one is worthy, his wife will be a helper & if not she will be against him. That can also be explained to mean, if one is not worthy to go on the right path on his own, then his wife will be כנגדו to push him to go the right way. This is why a woman has that power to influence her husband to put him on the right path. 

This is why Yaakov was punished. He knew this concept and therefore he should have let Dina marry Eisav so that she might be able to influence him & turn his life around. Sometimes, we have to put ourselves out there even though it might not look like the right thing to do.  However, we may have the power to influence other people, so  we have to put ourselves out there to do our part!