2019 The Shidduch Question That Must Not Be Asked
Chananya Weissman
Jul 12, 2019, The Times of Israel

“Are you currently dating? Can you send me a picture? I have a girl for you.”

That was the complete email from someone on the fringes of my life, who had never spoken with me about my personal life. For some inexplicable reason, his confidence that he had found my soulmate, or at least a likely candidate, failed to excite me. Was it the complete absence of tact? The distasteful – dehumanizing – request for a picture to be scrutinized by some stranger and her family? The presumptuous surety that my long fruitless search was over, and he was able to end it just like that?

I declined his request for a picture, he said okay, and that was that. I forgot to thank him for thinking of me.

A week later he approached me in shul and said he’d like to talk to me after davening. There is only one reason why someone would want to talk to a single man in shul. They have a girl for him. If no one has a girl for him, no one will talk to him. If he continues to go to shul for months or years in spite of this (no small feat), someone might eventually have a girl for him, without having previously talked to him. That’s how it works.

“She’s 29. She was married once for a short time. She’s pretty.” Then he told me what her brothers do for a living and what her father does for a living. I interjected that I wasn’t meeting them, and he hadn’t really told me anything about her.

“I don’t really know her,” he admitted. “I know the family. It’s a nice family.”

There were three ways the conversation could have proceeded from this point: the ideal way, the acceptable way, and the unacceptable way.

The ideal way would have been for me to say, “Sounds great! I’d love to meet her!” That would have made life most easy for the quasi-shadchan: accept his sales pitch with gratitude and no questions asked, sacrifice my own time and money pursuing his hair-brained suggestion, and offer him the hope to later boast that he “made a shidduch” and ride off straight into Gan Eden without putting in any real time or effort.

The acceptable way would have been for me to ask him virtually anything I wanted about the family. I could have demanded to know how much money they earn, who they go to for rabbinic advice, their hechsher of choice, where they daven, where they went for yeshiva and college, who they voted for, if they would be willing to support for me for several years if I married their daughter, various dubious indicators of their religiosity, if there is any mental or physical illness in the family, the dress sizes and head-coverings of choice of all the women in the family, the religious, educational, and financial credentials of all the men in the family, and much, much more. He would have agreed to find out all of the above and provide references upon request so I could do my own sleuthing.

That would have been the acceptable way for the conversation to proceed.

I chose the unacceptable way. I asked the only question that you are not allowed to ask, the question that will make these shadchanim who insist they are not really shadchanim upset with you and refrain from ever having a girl for you again.

“Why her and why me? Why not some other guy or some other girl? What makes you think we might actually like each other?”

It is unacceptable to ask someone who is confident that he has found the person who could well be your life partner, build a home with you, raise children with you, and grow old with you, why he believes this particular individual is suited specifically for you. It is unacceptable to ask why he thinks you might even want to go out with this person more than once, let alone all of the above. This is considered asking too much, giving the shadchan a hard time, and the reason why you are still single.

I chose the unacceptable way. I asked him this question. He was flustered and could not provide any substantial basis for the two of us to meet. I did another unacceptable thing for a single, and that was to lecture a shadchan. I told him it’s entirely random, everything he told me was a bunch of BS, he didn’t really try, and I don’t have the time or interest to meet random people for far-fetched dates. To his great credit he did not advise me to go to a dating coach or a therapist, nor did he call me bitter, though he might have been too shocked by my response (with time shadchanim get better at this). Instead, he squeamishly said he would meet the girl and try to get to know her (what a crazy idea), I doubt he ever did (who has time?), and thankfully that was the end of the saga.

The Orthodox community loves to organize conferences every so often where married experts can bloviate about what’s wrong in the shidduch world. Inevitably they will spend more time waxing about how difficult it is for shadchanim than for singles, and urge for shadchanim to get more respect, more money, and payments increasingly early in the process and with less expectations of actual success, just to keep them in the game. Whatever would we do if all the shadchanim in the world just quit? (Personally, I think it’s worth finding out. Can we try it for one year and see what happens? Six months?)

What you won’t hear is that the shidduch world – and by extension the overall community – is overrun with narcissistic shallow people, singles, parents, and shadchanim alike, and therefore systemic problems with the shidduch world and married life are inevitable. There is simply no other possible outcome.

If singles and whoever is representing them can ask all manner of petty, intrusive, even vulgar questions, but they cannot ask why this particular man should date this particular woman, why it really is worth a cup of coffee, why they should be excited to meet one another…if they cannot ask this question without getting strange and even hostile reactions, then perhaps it is the singles who should be getting paid to motivate them to agree to the date. And if it works out, they’ll pay the shadchan a hundred times the initial investment.

Give a single ten dollars to defray the time and cost of a blind date, and if it works out he will give you a thousand dollars in return.

The shadchanim and their clueless ilk will retort that singles would just take the money to go out and have a good time. And to that I say halevai.