The manufactured urgency that sees it as a “catastrophe” when the majority of girls are not married by age 20 is certainly part of the problem.
The result of this urgency is that the families of the young women are put in the position of having to launch an all-out desperate effort to snag one of the available good young men, while the families of the bochurim can sit back and wait in relative calm while the many offers pile in. The Gemara in Kiddushin 2b which states that it is the way of a man to pursue a wife, and not the way of a woman to pursue a husband, has lost all meaning. Instead, a herd mentality prevails whereby every young woman and her parents are told, explicitly or implicitly, that they better immediately get in the game when their daughter is eighteen, or else. They will be told “horror stories” about how difficult it is to find a shidduch, and how they must immediately make contacts with the shadchanim because any “good bochur” already has a long list of offers and they cannot delay. This of course contributes to the “crisis” when the desperate search does not produce results as quickly as desired. This is a problem only in the American Yeshiva world. That is not the case. The Israeli Yeshiva world has a very similar problem. The modern Orthodox also have a large and frightening problem of too many singles, as anyone familiar with the scene in Upper Manhattan is well aware of.
While there are some differences between these communities and the issues that they face, there are also commonalities that contribute to the problems in the Yeshiva oilam. Issues regarding parnassah, misguided priorities when looking for a shidduch, and of too much community pressure to conform to certain ideas and standards without allowing those who are a bit different to find their way within the community. It is true that too many have become desensitized to dealing with the issues. A compelling reason for that is that although there are fairly obvious problems with “the system” that are endemic; people throw up their hands knowing “you can’t fight the system – that is the way things are” and they cannot be changed. Most people do not like banging their heads against a brick wall; if they feel it is hopeless that change will happen, they turn away from the problem, as it is too stressful. The claim is made that the problem has nothing to do with money. By this Mr. Rechnitz means ostensibly that throwing money at the problem by creating programs, incentives, etc. (which Mr. Rechnitz has done and continues to do in a magnificent way) will not alone solve it. While this may be true, saying that money has nothing to do with the problem is very inaccurate; the fact is that money has everything to do with the problem.
To put it bluntly, as the Shidduch “system” now works, unless a girl is (in descending order of importance) either (A) from a wealthy family willing to support a young man for years in a comfortable lifestyle, or (b) very beautiful, or (c) has exceptional “yichus”, or possibly (d) has an unusual amount of talent or personality, her chances of finding a shidduch are drastically reduced. This is a sad fact, which any shadchan will confirm.
There is not much that can be done about factors (b)-(d). Heavenly gifts will be reacted to in given ways, and that is the way of the world from time immemorial. While more education might help mitigate these factors (as discussed below), there is no question that factor (A) has become horribly distorted in the yeshiva world, causing great misery. So long as it is expected that every young man be supported comfortably for years while learning in Kollel, and that every young woman is expected to marry a young man who will be learning in Kollel, a great premium will be placed on the girls who come from wealthy families, to the detriment of others.