(This should not be relied upon for practical halacha. When a question arises a Rabbi should be consulted.)
Section 2: Who Is Obligated To Pay The Shadchan
1. The Avnei Nezer (Choshen Mishpat 36) writes that the obligation to pay the shadchan belongs to the chosson and kallah. However, the parents customarily pay the shadchan.
2. Some poskim feel that because the parents customarily pay, the obligation to pay the shadchan now belongs to the parents, and not to the chosson and kallah (see Erech Shai Choshen Mishpat 185).
3. Harav Yisroel Belsky shlit”a also maintains that the obligation to pay the shadchan is that of the parents. He explains that even if the children do not live at home and are financially self-sufficient, as long as the parents are involved in the shidduch process, (giving the children advice, coordinating the vort and wedding), they bear the brunt of the obligation to pay the shadchan. However, if the parents are completely removed from the shidduch process, then they are exempt from paying the shadchan and the chosson and kallah must pay (Shu”t Shulchan Halevi Chapter 27 Note 2).
4. The Sefer Erech Shai (ibid.) agrees with the aforementioned poskim, who rule that a chosson and kallah who live with their parents are not obligated to pay the shadchanus (rather the parents must pay). He then adds that even if the parents cannot afford to pay the shadchan, the chosson and kallah still remain financially exempt. Harav Belsky shlit”a (ibid.) adds that while the chosson and kallah may not be obligated to pay the shadchan, if their parents cannot afford to fulfill the obligation, they should do their best to go above and beyond the letter of the law and complete the payment themselves. (see also Shu”t Teshuvos V’hanhagos vol. 3 457:3 and Sefer Yismach Lev page 22)
5. The custom is for the kallah’s family to pay for half of the shadchanus and for the chosson’s family to pay for the other half. This is so even if the Shadchan spent more time and effort with the kallah’s family than with the chosson’s family, or vice versa. If one family cannot afford to pay the shadchan, the other family is not obligated to pay the entire bill, but rather they should pay slightly more than half the bill in order to appease the shadchan and avoid any potential arguments (see Sefer Erech Shai Even Haezer 50, Shu”t Beis Yitzchak Even Haezer 115, Shu”t Binyan David 53:3, and Sefer Hanisuin K’Hilchosom).
Section 3: When to Pay-
6. The Rama (Choshen Mishpat 185) notes that the custom varies regarding when to pay the shadchan. Some pay immediately following the engagement (or tenaim), while others pay closer to the wedding. The Aruch Hashulchan (Even Hezer 50:42) writes that the custom in his area was to pay the shadchan immediately following the tenaim. [See also Sefer Halichos Yisroel 4]
7. The poskim disagree as to when to pay if there is no prevalent custom in the area (Rama and Taz ibid.). Harav Yosef Shalom Elyashiv zt”l writes that if there is no prevalent custom in the area, the payment is only required before the wedding and not following the engagement (Koveitz Teshuvos 1:207).
8. As cited above, many have the custom to pay the shadchan immediately after the shidduch is completed. Even if the shidduch is broken later, the shadchan does not have to return his fee (Aruch Hashulchan ibid.). The halacha may vary if the shadchan withheld information which, upon the uncovering of said information, led to the termination of the engagement. (See Shu”t Levushei Mordechai Tenina Choshen Mishpat 15 and Sefer Halichos Yisroel 11) For normative halacha, a rabbi should be consulted.
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