"How goodly are your tents, O Yaakov, your dwelling places, O Yisroel!"
There is an overwhelming shidduch challenge in our communities. There are countless young Jews, who despite their best efforts, have not found their match and remain single. As they get older, people stop worrying about them and trying to introduce them to potential matches.
As they get older and continue to remain single, they start to feel forgotten by the greater community. They can become depressed or lose hope, which can lead to spiritual decay and disease as well, G-d Forbid. Over time, they can begin to become less observant or even assimilate completely, God Forbid.
You must be engaged in helping other Jews find their soulmates, get married and start families of their own. This is an incredible mitzvah and zchus and an obligation that applies to everyone.
You must assume the responsibility to try and fulfill this mitzvah by helping "set-up" someone that you know, either a family member or someone else that you know through your social circles. There is even a greater mitzvah to try and help older singles find an appropriate match.
The Chatter is the Stan
Chazal taught (Sanhedrin 22a) that helping make a shidduch is as difficult as the miracle of the "Splitting of the Yam Suf, the Red Sea".
The AriZal explains (Shar Gilgulim, Introduction 20): When Hashem created the Red Sea during creation, there was a condition that it would split for the Jewish people in the future. However, when the Jews arrived after leaving Mitzrayim, the sea did not split immediately, because the Satan proclaimed that the Jews' sins made them unworthy of such a miracle, thereby denying them the opportunity to receive the Torah and build the Mishkan.
This is the similarity between this miracle and helping someone find a shidduch:
Before someone is even born, the Heavens have arranged a proper shidduch for that person. Everyone has a divine match in this world.
However, the Satan tries to claim that a person isn't worthy of their soulmate because of their sins. And, he uses deceit and trickery to try and prevent someone from marrying their shidduch. He tries to convince people to wait a little bit longer before they begin their search. Or, when a shidduch is proposed or people have met, he convinces outsiders, other people, to speak Lashon Harah about the couple; they defame a person and their behaviors ruining a shidduch over senseless and insignificant details that are irrelevant to the happiness and success of the shidduch.
All of this is for one purpose: to prevent a Jews from establishing a Jewish home and raising Jewish children who are committed to Torah and mitzvos.
You need to be diligent in protecting yourself and this couple from such evil trickery. When these challenges arrive, it becomes incumbent upon those involved to help by offering advice, speaking positively about the couple and the match, and guiding the couple to a happy and positive conclusion. With a little effort, we merit tremendous Heavenly help. And, what might have seemed like an unlikely or even impossible shidduch, can reach a beautiful conclusion.
The Mitzvah of Helping a Shidduch
When you help someone find their shidduch, you fulfill the mitzvah of tzedakah and chesed in a powerful way. When someone yearns for a soulmate and the opportunity to start a Jewish family of their own, but they cannot find a shidduch, they are impoverished by this unfulfilled need.
We find in Chazal (Kesuvos 67b) and in Rambam (Matanos Inyim, 7:3), that Hashem's command (Devarim 15:8) that we must help a pauper in a way that is "sufficient for his needs, which he is lacking", is referring to someone is single, they feel incomplete and lacking. You have an obligation to help someone fill that need by finding them an appropriate shidduch.
When you help them, Hashem saves you from the Heavenly accusers, as it says (Tehillim 109:31), For He will stand to the right of the pauper to save [him] from those who judge his soul.
Heavenly Partnership
When a person orchestrates a shidduch, they enter a partnership with Hashem, and they fulfill the mitzvah of (Devarim 11:22), and to cleave to Him.
The famed Rebbe from Belz, R' Yehoshua, zt"l, would offer delicious foods and wine to whoever met with him regarding a potential shidduch for one of his grandchildren. He explained that this custom was based on a section in Vayikra Rabba (8:1) that taught that every day Hashem is occupied with creating shidduchim. Therefore, when someone joins in this holy endeavor of Hashem, you need to show them honor and respect.
Returning What Has Been Lost
The Gemara says (Kiddushin 2b) that the process of seeking out a suitable match is comparable to someone looking for a lost object.
Therefore, the tzaddikim explained, helping someone find their shidduch is like fulfilling the mitzvah of returning a lost object.
On the other hand, if someone thinks of a potential shidduch but doesn't propose it, they need to be worried that they violate the law of ignoring a lost object, as it says (Devarim 22:3), "And so shall you do with any lost article of your brother which he has lost and you have found. You shall not ignore [it] ".
The Reward is Immense
The reward this mitzvah is incredible. Acts of kindness are one of the few mitzvos which we enjoy "their fruits in this world while the principle awaits in the World to Come" (Peah 1:1).
Helping make a shidduch also fulfills the mitzvah of Hachnasos Kallah, escorting a bride. As the Shlah HaKodesh explains (Pesachim, Ner Mitzvah, 56) that this mitzvah includes every detail that helps the couple enter the Chupah, and the reward is tremendous.
This also fulfills the mitzvah of being "fruitful and multiplying". The Maharsha explains (Shabbos 31a) that helping make a shidduch is what the Chazal is referring to when they taught that when a person enters the Heavenly Court they will ask him if he was engaged in "being fruitful and multiplying". All of the generations that come from a couple, all of the faithful Jewish families and homes that they build, are a merit to those who helped that couple meet and get married. This is what the Heavenly Court is asking them: did you help make shidduchim?
The Sefas Emes, zt"l, explained that Eliezer the slave of Avrohom merited to become a tzaddik because he helped arrange Yitzchak's marriage. R' Naftali Tzvifrom Ropshitz, zt"l, taught that when someone helps make a shidduch they are forgiven for even the most severe transgressions.
We find that there were many tzaddikim and great Torah scholars who were very involved in shidduchim, especially during the Ten Days of Repentance, to increase their merits. The Chasam Sofer, zt"l, was once late for Kol Nidrei because he was involved in helping with a shidduch! Many tzaddikim have also advised that men and women be involved in this process as a merit for various brachos.
How goodly are your tents
A matchmaker is like Yaakov Avinu, who was careful to talk a positive language, as it says (Breishis 27:22), "The voice is the voice of Yaakov"... His name was also changed to Yisroel when he overpowered Eisav's Angel and his army of 400 men, as it says (Breishis 32:29) "Your name shall no longer be called Yaakov, but Yisroel, because you have commanding power with [an angel of] God and with men, and you have prevailed. " So a matchmaker is also called Yisroel, because he overpowers the Satan and his messengers who try to prevent the establishing of Jewish homes.
This is possibly the meaning of the pasuk in our parsha, that the pasuk is talking to the matchmaker: "How goodly are your tents, O Yaakov, your dwelling places, O Yisroel! - How incredible is the goodness that comes from Jewish homes being established in your merit!? The reward is tremendous and immeasurable.
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