Sometimes you have to be hit over the head until a new idea
takes hold. One of the oldies was: shidduchim is such
a great chessed that no money can ever repay the
favor. The problem is that according to Halacha, this
does not hold true.
The Rama states that a shadchon must be paid in the
same manner that all services and products must be paid for.
The conditions are very exacting. "Beyomo titen
s'choro -- do not delay payment." This holds true
whether the shadchon serves as an agent who carries
out the parents' original idea, or whether he initiates his
own suggestions. The shadchon must be paid upon
delivery of services. The custom today is to pay at the time
of the engagement and not to wait for the wedding.
The Steipler in the name of the Chazon Ish taught that the
dictum that "most people are guilty of gezel" refers
to the fact that most people do not pay shadchonim
properly. He considered the matchmaker's fee ultimately
kosher money. Rav Chaim Kanievsky relates the following:
The Chazon Ish once counseled a childless couple that they
should pay shadchonus even though in their particular
case, they were exempt. Within a year they had a baby boy.
The only money which the Maharil used was shadchonus
money, and the Chofetz Chaim commented that he would buy
himself shrouds from matchmakers' fees since this was kosher
money.
The word shidduch comes from the Aramaic "shadint
ara -- and the land was quiet." The atmosphere calms
down after an engagement. The disagreements and uncertainty
that precede the engagement dissipate and calm prevails. An
alternate explanation is that before singles find their
mate, they are worried and unsettled; after the
shidduch is finalized, calm descends.
Kerem Shlomo quotes Pachad Yitzchok that it is
a mitzva to engage in matchmaking. Just as the Torah
was brought to Klal Yisroel through an agent, Moshe Rabbenu,
so, too, a bride is brought to a groom through an agent. It
falls into the category of the mitzva of "cleaving
unto Hashem," that is, emulating His ways. The Midrash
Rabbo Bereishis states that following the completion of
Creation, Hashem has occupied Himself with making matches.
And one who makes matches, is emulating his Creator!