A dating column in a Jewish newspaper recently raised an interesting dilemma: If after the first date one is interested in seeing the other party again, how long should he or she wait before expressing this interest to the shadchan?

This is in fact quite a conundrum. Calling the shadchan immediately after the date with positive feedback makes one appear desperate. But if one waits too long before calling the shadchan, the other party might take it as a sign of disinterest and move on to the next person in the frozen meat section. (And you think you’ve got problems!)

The column’s advice (wait three days before calling the shadchan) is irrelevant. The question itself is what’s most disturbing, for it presupposes a number of things that should not be presupposed:

First, that no good Jewish boys or girls will find themselves on a date without the involvement of a shadchan. It’s simply taken for granted that this is the only appropriate way for dates to transpire. How this baseless dogma ever took root among the am segula is a mystery to me.

The second presumption is that it is inconceivable for a man to say to a woman (after all, we are dealing with adults who are ready for marriage, are we not?) at the conclusion of the first date “I had a very nice time, and would like to see you again.” No, they must awkwardly part ways as if the whole date was a charade, then report back to one or more intermediaries. His people will get back to her people, and her people will get back to his people, and after days or weeks of phone tag and negotiations they will determine if there will be another act to this abnormal play.

The third, most damaging presumption is that one should not readily express interest in the person he is dating. Dating is like a poker game or a business deal. Expressing a desire to see the other person again is a sign of vulnerability, a forfeiture of control. Now the other person has the exclusive right to be the rejecter; you can only be the rejected. The boy and the girl must therefore posture and pretend that they don’t really like each other (just a little). They must avoid any meaningful expression of interest, lest they appear “desperate” (as if they’re not both looking to get married), and thus less of a “catch” (as if they’re fish). I wonder how many potentially wonderful shidduchim never go through because of this foolish obfuscating.

Everyone will agree that one of the foundations of a successful marriage is healthy communication. Yet singles are trained to avoid communicating with one another about where their relationship stands and where it might be going. They have agents for this, who continue to oversee the relationship until it is deemed ready to become “serious” (what is it until then, a joke?).

I understand why people encourage singles to suppress, or even repress, affectionate feelings for the other person. Were these feelings not reciprocated, the boy and girl would have an awkward situation on their hands, in which communication would be difficult and feelings might even be hurt.

But dating by definition is all about forming a relationship that should last and continue to grow for a lifetime. By necessity this means opening oneself up to possible rejection and hurt feelings. Those closest to you have the greatest ability to hurt you – but we have a natural need to be close to other people. Avoiding direct expression, which has become de rigueur among religious Jews, flies smack in the face of the very reason for dating. I firmly believe that this not
only impedes proper shidduchim, but is a primary cause of the sharp rise in unhappy and abusive marriages.

In the old days, before every aspect of dating was agonizing and pressurized, it was standard for men and women to decide immediately after a date, or even during the date, if they would see each other again. The guy would say something like “May I call you Tuesday evening?” if he was interested, and the girl would accept or decline, and that was that. If the guy was not interested, he’d take her home and wish her well, and that too was that. (If the guy was gutless, he’d promise to call but never follow through.) On those magical occasions when the interest was mutual, they continued the relationship without ambiguity or unnecessary external meddling.

Nowadays, even if the first date is wonderful beyond belief, they dash cold water on things at the end and pretend that they didn’t really enjoy each other’s company as much as it seemed. An element of doubt and fear is intentionally introduced into the situation as a defense mechanism. The willingness to display interest and affection with no guarantee of it being reciprocated, the ability for singles to openly communicate with one another about their relationship, is ripped out of dating – the shadchan will get back to you with the verdict. For every baby step forward in the relationship they must immediately jump back three-quarters of a step, as if cautiously testing a hot bath.

Honestly, the day will come when a boy proposes to a girl through an intermediary. It’s the same logic, merely extended to the point of absurdity.

Rejection will hurt whether it comes immediately or days later through an intermediary. No matter how sensitive one tries to be, it is sometimes unavoidable to add to someone’s disappointment and frustration. Hiding behind an intermediary makes it easier for the one doing the rejecting, but ultimately this stunts the ability of singles to communicate and develop a healthy relationship with the opposite gender. Perhaps if they developed these vital skills, they would learn to soften the impact of rejection without hiding behind a spokesperson. Inhibiting singles from communicating at any stage of the relationship leads to far greater problems than the ones this approach purports to solve. 

So let’s stop playing games. The willingness and preparedness to communicate should be a prerequisite for dating. Parents and shadchanim should encourage singles to take charge of their own relationships, to communicate openly and honestly with the people they date. This will ultimately lead to more shidduchim and happier marriages, which is well worth the growing pains it may entail. 

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Rabbi Chananya Weissman is the founder of EndTheMadness and the author of seven books, including "Tovim Ha-Shenayim: A Study of the Role and Nature of Man and Woman." Many of his writings are available at www.chananyaweissman.com. He is also the director and producer of a documentary on the shidduch world, "Single Jewish Male." He can be contacted at [email protected].