Rebbitzin, your back-up solution is one up for discussion. Having the condition be to make a shidduch or show effort to do so in general, and not limiting it to just to getting their own class married will be much more productive as my hypothetical cases shows.
But again, you have to realize that some people are good at making shidduchim and have a lot of siyata dishmaya, and others are not. Also, shidduchim can take time to come to completion- and engagements should not be longer than necessary. The couple can take a kabala on themselves to try, and show their effort. But I doubt every couple will be able to pull off a successful shidduch, even if given a year or 2 to do so after their wedding.
I have another suggestion that might be more practical, and still accomplish what you want- which is that couples should care and try to help those “left behind”. Each class should set up a database with every girl, her details and what she is looking for. As girls get engaged, they should get info from their chassanim on the single boys that they know and enter them in the database. There would be a programmer/database manager as well as an actual shadchan who would make the matches through the database. These would receive some salary for their work from a fund set up by each couple who gets engaged- perhaps they could use the masser money from their chasanu presents if they don’t have other funds, or make it some % of the total wedding expenses. This is something positive they can do to help others with shidduchim without being penalized for other people’s personal decisions.
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