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The Shulchan Aruch beginning of Even Hoezer tells that in early generations a man past twenty who was not pursuing marriage properly was brought to Beth Din and instructed to get married.
Now, this can make a lot of problems. Let us say that in a certain town an older man can only marry people he doesn’t want to marry. Can he be forced to marry someone against his will?
We had a case like this with the brother-in-law of the Baal Shem Tov. Reb Gershon Kitover. In his older years he went to live in Israel, in Jerusalem, where the Orach Chaim HaKodosh, considered the greatest saint of his time, was the Rov. The Orach Chaim honored him with being the Baal Tefila for Rosh HaShana. But then Reb Gershon was told that the rule in Jerusalem was that nobody was allowed to live there as a single. There are letters that Reb Gershon wrote about this, and he asked, How can I marry somebody from a different world? It is not known what happened. But this kind of a problem surely existed in earlier generations. And when people were forced to marry without wanting their partner, only problems could result.
The problems were so strong that the Beth Dins eventually surrendered and did not force people to marry. Some offered proofs that today we don’t force marriages. But others disagreed and said we must have marriage. But if by so doing the Beth Din will create a constant ruckus that destroys the Honor of the Torah, it may be prudent to refrain from this forcing of marriages. Still others maintained that even today marriage should be coerced.