“We Have to Skip Our Oldest Daughter… but How?!”

I am sending this question with tears in my eyes and disbelief in my heart. My daughter is 26 years old and still not married. We’d asked her younger sister to refrain from dating until now, but in two months she will be turning 22, and we no longer feel it is appropriate to hold her back.

I don’t even know what my question is. It breaks my heart to do this, but I don’t see another choice. My older daughter has not expressed a desire either way ® she hasn’t asked my younger daughter to wait, but neither has she insisted that she begin.

How do we handle this? Any tips for mitigating the pain and easing the process?

Brokenhearted Mother

Dear Mother,

IF pages could speak, this paper would be telling the story of impossible choices. Some of the hardest moments of parenting are those when we’re asked to choose between the needs of one child over another. This is a hefty nisayon, and I bentsh you to have the siyata d’Shmaya to traverse this path b’shalom. Let me underscore the importance of daas Torah in this situation. Every family facing this dilemma needs to have the guidance of a rav who is familiar with their specific situation to guide them through this. This is too big to tread alone.

I recently had the zechus to meet with a group of older single women on the topic of “skipping” — younger siblings who marry (or even date) before their older sibling. The pain was palpable — so was the inspiration. I learned a lot, and I’m sharing it with you in hopes that we can lessen the hurt.

I discovered two significant patterns regarding the women who were “skipped”:

1) The women who were treated with respect fared significantly better than those who were not.