The shadchan (matchmaker) often fills a vital role for those seeking their soul mate. We are taught that God Himself spends most of His time these days as a shadchan, matching men and women to one another.
To be a good shadchan is actually hard and tedious work. A shadchan must gather and process all the relevant information about his or her “clients” in order to competently suggest a match worthy of pursuing. The shadchan also serves as an intermediary between the man and the woman, and often between the parents of each side, throughout the dating period. Indeed, contrary to popular misconception, it is actually forbidden to marry someone without meeting them first. It is interesting to note that the word "shidduch" means "peaceful" in Aramaic, though shidduch arrangements and negotiations are often anything but “peaceful.” It has also been jokingly suggested that the word "shadchan" is an acronym for the words "sheker dover kesef notel," meaning, "one who speaks lies and takes money."
Suggesting a match is not something just for professional shadchanim. Everyone should try to suggest possible shidduchim, and doing so is a great mitzva. It is permitted to discuss and deliberate shidduch-related matters on Shabbat. A shadchan must be exceptionally careful not to violate the prohibition of lashon hara, forbidden speech, when discussing shidduch candidates. At the same time, it is crucial not to withhold vital information from a shadchan that might truly be needed in order for the other side to properly make an informed decision about a prospective spouse. It goes without saying that one must not give over false information, either. In ancient times, it was the rabbis and scholars who served as shadchanim. This is because such people could be trusted to embellish and exaggerate as appropriate without a concern that they would tell outright lies about a shidduch that they were suggesting. They were also likely better versed in the laws of lashon hara than anyone else. We are advised against getting involved with arranging shidduchim for non-Jews.
Unfortunately, it is not uncommon for potential marriage partners to be rejected or engagements to be broken over ridiculous and illegitimate considerations. For example, one should not decline a shidduch proposal or break off an engagement if it is discovered that the potential spouse is a ba’al teshuva (regardless of their background), or that a grandparent was a convert, or the like. One should also not break off a shidduch due to the discovery of a disease or other troubling medical history that is determined to have been cured. In fact, there is no reason for such information to even be disclosed.An existing illness, however, must be revealed if it is likely to deter someone from getting involved with the shidduch in the first place. There is an opinion that no negative information need be disclosed until the couple becomes serious with one another. One may generally not impose or intrude on the proceedings of a shidduch without explicit permission to do so.
Although as a general rule, one should not charge money for performing a mitzva, shadchanim, even amateur ones, are excluded from this restriction. This is because shadchanim are deemed to be professionals from the perspective of halacha, and just like all other tradesman, they are entitled to a fee for their services. This is true even if the shadchan’s services were not solicited and the shadchan simply got involved on his or her own. It is taught that those who neglect to pay the shadchan's fee are inviting all sorts of troubles into their marriage. A shadchan who was not paid is perfectly entitled to take his case to a Beit Din for arbitration. While the shadchan's fee should truly be paid by the bride and groom themselves, common custom is for the fee to be paid by the parents of the couple. In fact, even if for whatever reason the parents of the couple neglected to pay this fee, most authorities rule that the bride and groom cannot be forced to pay it.
There is no set amount that a shadchan must be paid. As such, the shadchan should be paid in accordance with local custom, and the fee should be divided equally between the two sides. “Local custom,” for this purpose, is generally considered to be the custom of the community in which the shadchan resides. Therefore, the fee for a shidduch made between one who lives in North America and one who lives in Israel depends on where the shadchan resides -- not the bride or groom. Other authorities rule that each side should pay half the shadchanut fee that is customary in their community. Some authorities suggest that shadchanim should be paid one thousand dollars for their services. There are other approaches on how a shadchan should be paid, as well.
In the event that a shadchan worked especially hard, or making the shidduch was especially tedious, the shadchan may be entitled to extra remuneration. A shadchan who originally offered his services for free cannot later retract and demand payment for having made the shidduch. Of course, if a shadchan chooses to waive his or her fee there would be no obligation to pay it. One should give some type of gift or honorarium to someone who suggested a shidduch even if that person played no role in the subsequent arrangements and negotiations. God rewarded Moshe Rabbeinu for having been the shadchan between Him and the Jewish people. It is taught that those who are having trouble finding a spouse should be especially meticulous with the recitation of Kiddush Levana each month.
In some communities, it is customary to pay the shadchan immediately upon the announcement of engagement. According to this custom, the shadchan is not required to return the money if the engagement is later broken off. In other communities, the shadchan is only paid after the couple is married. In a place where there is no set custom, the one who hired the shadchan can choose when to pay the fee, whether at engagement or after marriage. A number of authorities encourage rabbis to inquire whether the shadchan has been paid before agreeing to officiate at a wedding.
Although a shadchan serves an important and even sacred role in Jewish family life, turning to a shadchan should not be the only channel to pursue when seeking a mate. Indeed, the only figure in Tanach who explicitly made use of a shadchan was Avraham in his search for a wife for his son Yitzchak. All other biblical and Talmudic figures seem to have found their soul mates on their own. Indeed, one should never forget that it is God Himself who is the ultimate shadchan and all others are merely His agents.
 Sota 2a; Bereishit Rabba 68.
 Kiddushin 41a.
 Targum Yonatan Ben Uziel, Shoftim 3:11.
 Maharach Or Zarua 3. See also Ma’amarei Admor Hazaken p. 90.
 Shulchan Ha'ezer 3; Minhag Yisrael Torah, EH 26:1.
 OC 306:6.
 See Tzitz Eliezer16:4:1.
 EH 39:5; Igrot Moshe, EH 4:73:2; Minchat Yitzchak 5:44.
 Me’il Tzedaka (Landsdorfer) cited in Otzar Hayediot (Stern) Vol 1. p. 230.
 YD 151:14; Chavot Yair 185; Mahari Assad YD 230:2; Be'er Heitev, YD 2:15; Emek Halacha 1:46.
 Teshuvot V’hanhagot 1:632, 2:627. See also Rivevot Ephraim 3:405; Shevet Hakehati 2:321.
 Teshuvot V’hanhagot 2:628.
 Ibid., 2:623.
 See for example: Rambam, Hilchot Issurei Bi’ah 15:3; Kehillat Yaakov, Yevamot 44; V’ha’arev Na, vol. 2, p. 188.
 Teshuvot V’hanhagot 2:624.
 Minchat Yitzchak 7:93. See also Igrot Moshe, EH 4:73:2; Tzitz Eliezer 13:81:2; Meah She’arim 215.
 Igrot Moshe, OC 4:118.
 B'tzel Hachachma 3:10; Aruch Hashulchan, EH 50:42.
 Bava Metzia 63b; Rema, CM 87:39, 185:6,10, 264:7; Shach, CM 264:15; Teshuvot Maharash Engel 3:15.
 Bava Metzia 101a; Biur Hagra, CM 87:117; Halichot Yisrael 1:1.
 Divrei Yechezkel Hachadash p.114.
 Rema, CM 87:39.
 Avnei Nezer, CM 36; Halichot Yisrael 1:2,3.
 Erech Shai, CM 185.
 Pitchei Teshuva, EH 50:16.
 Erech Shai, EH 50.
 Teshuvot V'hanhagot 3:457.
 Igrot Moshe, CM 2:57.
 Rema, CM 264:7, 335:1; Shach, CM 264:15.
 Teshuvot V'hanhagot 3:457.
 Pitchei Teshuva, EH 50:16.
 Pitchei Teshuva, EH 50:16; B'tzel Hachachma 3:10.
 Yalkut Shimoni, Yitro.
 Rivevot Ephraim 5:503.
 Aruch Hashulchan, EH 50:42; 185:11, Halichot Yisrael 1:2,4.
 Aruch Hashulchan, EH 50:42; Kovetz Teshuvot 1:207.
 Rema, CM 185:10.
 Levushei Mordechai 11.
 Bereishit 24:2.