(This should not be relied upon for practical halacha. When a question arises a Rabbi should be consulted.)
There is a mitzvah for one to be involved with making shidduchin between a man and a woman. Hashem was the very first shadchan uniting Adam with Chava.
Section 1: The Obligation To Pay The Shadchan-
1. As with any other business transaction, a shadchan must be paid a fee for arranging a shidduch (see Rama Choshen Mishpat 185).
2. The poskim stress the importance of paying shadchanus (paying the shadchan). Harav Mordechai Winkler zt”lai, writes that many rabbanim, himself included, refused to orchestrate a wedding (serve as the mesader kiddushin) if the shadchan was not yet paid (Shu”t Levushei Mordechai 11).
3. Many poskim write that paying the shadchan is a segulah for having children (see Sefer Maaseh Haish vol. 1 page 215) and for shalom bayis [marital peace] (see sefer Netai Gavriel on Tenaim page 386 and Sefer Hanisuin K’Hilchosom chapter 4).
4. It makes no difference whether the shadchan was hired by one of the parties or if he volunteered his services. In either case he must be paid for his services (see Biur Hagra 185:13 and sefer Simcha Laish 10).
5. Even a non-professional shadchan must be paid for his services (Hanisuin K’Hilchosom ibid.).
6. If need be, the shadchan may petition a beis din (Jewish court) to force the parties to pay his fee (Levushei Mordechai ibid.).
7. The shadchan gets paid even if he did not exert a significant amount of work for the shidduch. Merely arranging dates/meetings over the phone is enough to warrant payment (Edus Biyehosef 2:35).
8. One is not allowed to use “maaser money” to pay for obligations and debts. Therefore, one is not allowed to pay the shadchan with “maaser money.” (see sefer Zichron Yehuda 192 and Sefer Emes L’Yaakov on the laws of Tzedaka)
9. Harav Gavriel Zinner shlit”a rules that if one agrees to pay the shadchan more than is the standard fair, he may use “maaser money” to pay the amount that is above the standard fair (Netai Gavriel ibid.).
10. There is no obligation to pay, if the shadchan states that he does not want to receive payment for the shidduch (Pischei Teshuva Even Haezer 50:17). Harav Moshe Shternbuch shlit”a explains that this is only true if the shadchan explicitly says that he will not receive payment for the shidduch. Merely saying the phrase, “I do not work on shidduchim for the money” does not remove the responsibility of payment from the couple. When that statement is said, the shadchan is merely trying to relay the message that the main reason that he became a shadchan was in order to help people. He still requires payment for the shidduch (Teshuvos V’Hanhagos vol. 3 457:3).
11. If the shadchan absolves all parties from payment he may not change his mind after the engagement or wedding and then demand payment (Minchas Yechial 2:4). However, as long as the shadchan is still working on the shidduch (before the engagement or before the shadchan is “removed” as the middleman) he may change his mind and may refuse to continue working unless he will get paid if the couple marries, and at which point the families will be obligated to pay the shadchan the full fair that a shadchan normally receives.
12. Harav Moshe Shternbuch shlit”a writes that he has heard that in many sefardic communities the custom is to not pay the shadchan (Teshuvos V’Hanhagos 1:736).
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