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Winnie, how many of your hypotheticals apply also to students not placed in schools because of their “issues” (such as students that need special ed or emotionally unstable for formal schooling or deaf or blind etc)?
Your arguments could equally work against the “all students are placed in a school or no school opens”, and I honestly don’t know “the how” that the edict in Lakewood worked to deal with such situations, but, guess what, IT DID!!
I modified my suggestion from the original “no chuppah till all girls of class engaged (subject to exemptions)” to “every chosson kallah must make another shidduch before their chuppah”. The Rov can be shown that they made sincere hishtadlus but were not matzliach to fruition, which would be acceptable.
So what’s wrong (actually, what is right) with a takona that each engaged couple must make another shidduch (or at least present proof to the mesader kuddushin of their hishtadlus)?
One hypothetical you raised: A girl that gets engaged to someone from a different “type”, (example Modern Orthodox or from a different chassidus), in today’s worls, everyone knows people that know other people…(the MO might have only MO friends but might be neighbours with someone suitable, might meet in business soneone suitable, might have relatives that know someone suitable etc).
This takona would benefit everyone, including the chosson kallah, as they are going to the chuppah with the tremendous zchus that they helped build another bayis ne’eman b’yisroel and knowing that they prepared for their wedding with more substatial things that the style of gown and color scheme..