Questions on Parshas Vayishlach to think about and discuss:

1. Why does the Torah detail the whole process of how Yakov dealt with Esav?
2. Once Avrohom’s name was changed we are no longer allowed to call him by his previous name Avrom (unless when learning those pesukim in the Torah) (17:5). Why then do we find that after Yakov’s name was changed to Yisroel (32:29) we can still call him by his previous name of Yakov?
3. Was the hiding of Dena from Esav a correct thing to do?
4. Why did Rochel die and was buried on the way, not meriting to be buried in Meoras Hamachpeile?
5. How old were Yakov and Esav when they met in Parshas Vayishlach?
6.  How old was Rivka when she died?
7. How old was Rochel when she died?
8. How many great people died in Parshas Vayishlach?
9. Why are the Jewish Nation sometimes referred to as Yisroel and sometimes as Yakov? What is the difference between these names?
10. How do we see a different outlook on life between Yakov and Esav?
11. Rashi (32:5) brings two opposite approaches from the same possuk! Firstly, he says that Yakov seems apologetic and on the defensive that the brochos have not really worked. Then he brings that Yakov is on the attack warning Esav to beware since he has kept the mitzvos and not learnt from Lovon’s evil actions. How can both these explanations coexist?
12. Rashi (32:9) brings that Yakov prepared himself against Esav with three things. With a present, prayer and to fight. Why the need for all these three types of approaches and not simply pick one of them?
13. Esav comes to attack with four hundred men (32:7). What is significant about this number? Why not get a far larger army?
14. How many soldiers were in Esav’s army?
15. Why was the holy Yakov scared of Esav?
16. The Jews’ multiplication are compared to the sand next to the sea (see Rashi 32:13), the earth of the land and the stars of the heavens. Why the need for three different examples? What is the difference between them?
17. There are different words for presents. Why is the present from Yakov to Esav given a new name – “Mincha“?
18. Yakov sent to Esav five different types of animals (32:15-16): goats; sheep;camels;cows and donkeys. Why these and this number? Why by all of them does it mention first the males and then the females and by the camels it only mentions females and their children?
19. Rashi (32:8) brings that Yakov was scared to kill others. Why should he be as the halacha is that if someone comes to kill you then you should kill him first?
20. Rashi (32: 23) brings that since the possuk mentions only eleven children, Dena was hidden away from Esav. What we see from the possuk is that one of the children was missing. How do we see that it was Dena more than any of the other shevotim?
21. How could Yakov, a human being, fight an Angel, the Sar Shel Esav – a spiritual being?
22. When Yakov finally met Esav he bowed down to him seven times. Why specifically this number?
23. Why is Rivka’s death not clearly mentioned in the Torah? (see Rashi 35:8)
24. Why did Yakov bury the spoils of Shechem that were given to him by the shevotim and not simply destroy them? This is especially so since these idols were dug up later in history and used by the Kutim at the top of Har Grisim (see Tosfas Chulin 6a)?
25. What is the significance of particularly Rochel being the only woman in the Torah to die of childbirth and that this happens by the birth of Binyomin?
26. What is the significance that all the Shevotim were born with one twin sister while Binyomin was born with two (Rashi 35:17)? (We find the same idea that Kayin and Hevel were both born with twin sisters but Hevel also had an additional one – see Rashi Bereishis, 4:2)?
27. How are we to understand the episode of Reuven and Bilho (remembering the Gemora in Shabbos 55b that whoever says Reuven sinned is making a mistake)?
28. Why at the end of Parshas Vayishlach does it describe at length the descendants of Esav (and others)?

Ideas for answers on the general parsha:

1. The Ramban (introduction to Parshas Vayishlach and 33:15) explains that it is to teach us in exile how to deal with the goyim as seen in how Yakov dealt with Esav. Great Jewish representatives would specially learn this parsha before travelling to Rome on behalf of the Jews.
2. Really we should only call him Yisroel. However, since the pesukim themselves afterwards still call him Yakov we therefore see that this is permitted. This is not the case with Avrohom and therefore Avrom is no longer his permitted name.
3. Rashi (32:23) seems to say it was incorrect as Dena could have potentially influenced Esav to be good. Others say that of course she should have been hidden from this rosha. However, the wrongdoing was in the way he went about it being overzealous to hide her.
4. Rashi (31:32) brings that since Yakov cursed anyone who had stolen the terofim from Lovon, and it had been Rochel, she therefore died on the journey. Rashi (30:15) brings another reason. When Rochel gave up her night with Yakov in exchange for the Dudoim, since she put down the importance of being with Yakov she did not merit to be buried next to him.
5. Yakov and Esav were they same age – they were twins. Yakov was 63 years old when Yitzchok blessed him. He spend 14 years in Yeshivas Shem Voever (Rashi, 28:11). He then spend 20 years by Lovon (31:41) – 7 years for marrying Rochel and 7 years for marrying Leah, and then 6 years working with the sheep. This makes them both 97 years old when they met in Parshas Vayishlach.
6. The Biur HaGra to Seder Olam 2 brings that Rivka died when she was 133 years old.
7. The Midrash Seder Olam (Chapter 2) brings that Rochel died when she was 36 years old.
8. Devora, Rivka’s nurse (35:8) and hidden here is also Rivka’s death (Rashi). Rochel (35:19) and Yitzchok’s death (35:29).
9. It depends on the spiritual level of the Jews as to which name they are referred to. We see from the meaning of the names what level they refer to. Yakov refers to a crooked way (see 27:36) and therefore to a lower spiritual level while Yisroel means straight (Yosor) referring to the higher spiritual level.
10. Esav says he has a lot (33:9) while Yakov says he has everything (33:11). In life we can have the view that we deserving nothing and then we will be grateful for everything that we have or we can expect things coming to us and therefore are happy with a lot but want more.
11. Perhaps the idea is that Yakov deals with Esav in two different ways. On the outside, he appears to appear submissive. However, on a deeper inner level, Yakov is not scared at all.
12. Perhaps the idea here is to show what a Jew should do in such situations. We believe that a person must do hishtadlus, to work within the nature framework. However, this comes together with prayer, realizing that all is decided by Hashem. Perhaps this is reflected here. Yakov did the prayer and also did histadlus.  This part was reflected with two sides of the coin. He decided to try first the friendly approach within nature by sending the presents. However, if this did not work, he prepared himself within nature for the possibility of battle.
13. A start to this is that 400 is 4 times 100. 100 is just an extension of the number 4. The Maharal tells us that the number four represents dispersion as seen in the four directions of the world. The strength of the Jewish Nation seen in Yakov and the twelve shevotim is Achdus, unity. (The Maharal, Ner Mitzvah, sees this in the word אחד where א is Yakov, ח is the eight children of Rochel and Leah and ד  the four children of the maidservants.) Esav is the opposite as seen in the sword that cuts things and separates them. 400 men expresses that Esav was coming to cut and oppose the unity seen in Yakov.
14. The possuk (32:7) says that Esav came with 400 men. Chazal say that this means 400 (main) men, i.e. generals. Under each general were 400 hundred men. This made a total of 160,000 soldiers!
15. Rashi (32:8) brings that he was scared that he and others would be killed. The Targum Yonason says that he was scared of the merit that Esav had of excelling in honouring his father. (This is similar when Moshe was scared of the giant Oig because of his merit in telling Avrohom about Loit’s capture. We see here that these great people were not scared of the physical aspect but of the spiritual merits!) The Ba’al Haturim brings that he was scared that his family would be killed. The Gemora (Brochos 4b) brings that Yakov was scared that he might not merit being saved perhaps due to a sin.
17. The Sechel Tov answers that the word “mincha” comes from the word “menucha” reflecting that through this present Yakov “rested” and managed to placate Esav’s anger.
19. The Gur Aryeh answers that Yakov was scared of the consequences. With Esav’s death then Yitzchok would curse him. Tosfas answers that he was scared that instead of killing them it would have sufficed to just maim them. Perhaps another idea is that even though he could not help to kill them he was worried on the after affects. Naturally such an experience would make a person less sensitised to killing and naturally feel more prone to killing again.
20. Perhaps the reason is because we find that Esav pursued women and therefore they would be the ones open to danger. There was only one daughter. However, the boys had no extra reason to be scared that Esav might harm one more than any of the others. If they were all in danger then all of them should have been hidden. It is therefore reasonable to assume that the one hidden was Dena.
21. Perhaps we see from here the greatness of the Avos that they were like Angels themselves having reached such a high spiritual level. This explains how he could fight another spiritual being. Alternatively, perhaps Yakov was assisted by his own spiritual Angel to oppose the Angel of Esav.
22. Perhaps the idea is that seven is the number that represents nature. This is seen in the seven days of the week and the seven colours of the rainbow and seven musical notes. Esav combats Yakov in the natural realm of this world. Yakov wants to placate and pacify Esav and therefore specifically bows down seven times to express submissiveness in the natural realm.
23. Rashi (35:8) brings the reason for hiding the death of Rivka is so that the world should not curse the mother who brought Esav into the world. If so, why then not also hide the death of Yitzchok for the same reason, being the father of Esav? …
25. It seems to be that Rochel and Binyomin could not coexist for some reason resulting in Rochel’s death by Binyomin’s birth. The Mishna and Gemora Shabbos (31b-32a) brings that childbirth is a dangerous time for the mother. We know that the great Rochel was careful in all the areas mentioned there that could cause death during childbirth. Therefore there must be some other reason. …
28. Rashi (36:2) brings that it is to show the rampant immorality amongst the descendants of Esav. This is in stark contrast to the Yichus that is so important amongst the Jews.