Comparison Shopping and Shidduchim

By Chananya Weissman

I used to wonder how some people have the daring to date more than one person at a time. Nowadays you’d be hard-pressed to find anyone in observant Jewish circles who engages in this practice, let alone willing to own up to it. It’s one of those things that is not only “just not done”, it’s downright unthinkable.

At first glance, dating multiple people concurrently seems more appropriate for a sitcom than a serious-minded and compassionate Jew. After all, at least one of these relationships is certain not to result in marriage, and would thus seem to be entirely frivolous. Furthermore, it presents a rather tricky dilemma: if one divulges to his date that there’s “someone else” he stands a good chance of having that problem solved shortly thereafter, but keeping it a secret for more than a couple of dates will inevitably lead to duplicity. It’s no surprise, therefore, that the modern-day Jew, ever fearful of a risk of any kind, is repelled by the thought of dating more than one person at a time.

As is often the case, however, this position that is so commonly taken for granted actually stands on very uncertain ground. For starters, in all other acquisitive endeavors we engage in what is known as “comparison shopping” or “exploring our options”. Have you ever heard of someone who visited a house for sale and subsequently refused to read the real estate section until he made up his mind about it? Would we advise someone looking for a job to turn down potential interviews, regardless of how promising these opportunities may be, until they finalize things one way or the other with their first interviewer? When considering schools for ourselves or our children, do we visit and apply to only one institution at a time, for fear that we may be accepted by or develop interest in more than one? Do we waste many weeks on a single lukewarm option only to be brought back to the drawing board?

No one would argue that this behavior is absurd, reckless, potentially self-destructive – yet this is precisely the sort of behavior that is expected on the shidduch scene. What is responsible behavior in all of our other searches is suddenly considered foolish, reprehensible, or a lack of bitachon in the most important search of all!

Two anecdotes, whose authenticity is confirmed, come to mind. A guy is set up with a girl. He calls to arrange a date, only to be informed by the girl that she cannot go out with him; someone she had gone out with two weeks before had just called her for a second date. Leaving aside the question of why she would agree to go out with someone who takes two weeks to call for a second date, the rational mind can only wonder about the rules that presumably govern this situation. Did the young lady sign a contract two weeks ago granting the gentleman “exclusive rights to all future dates until such time as the relationship is definitively terminated by one or both parties”?

Anecdote number two: a guy and a girl work on a project together and develop an interest in one another. The guy asks the girl out, and is turned down – but not for lack of reciprocal interest. Mere hours before the date was requested, the girl had gone out on a blind date with someone else. The date was okay, and she consented to a second date. She admitted that she was interested in the first gentleman, and that had he asked her out first she would have readily accepted. However, now that she had gone out with this other person, it would be unfair to start seeing someone else – even someone she knew better and had more of an interest in! In other words, a mere chronological advantage trumps all other considerations. Many people regurgitate the same clichéd, half-baked reasons not to date more than one person at a time. The most common reason is that it is “unfair” to the other party, a sort of cheating, adulterous behavior – notwithstanding the fact that these people have as yet no commitment to one another.

Again, we would do well to consider the advantages of comparison-shopping, and to recognize that there is nothing duplicitous about considering more than one option at a time. Quite the contrary, we owe it to ourselves and everyone else involved to make the most informed decision, and it is understood that an initial meeting, interview, or test drive is nothing more than that. As a Rebbe of mine succinctly put it, “the girl has the same heter.”

Those who argue that dating more than one person at a time blurs one’s ability to make an informed decision need to explain in conclusive logical terms how this differs from all similar situations in life, where concurrent, “head-to-head” comparisons are superior to standalone comparisons. Barring such conclusive support, their position should be rejected in favor of what holds true in every similar circumstance.

I’ve seen it written by self-proclaimed authorities on shidduchim that dating more than one person at a time causes one to confuse one person for the next. (Interestingly, people don’t seem to have this problem of “keeping track” with one’s friends and family members.) I submit that one who suffers from this problem has more to worry about than how many people to date at a time.

Others, bringing vague Torah arguments to support an otherwise untenable position, claim that dating more than one person at a time demonstrates a lack of bitachon. We should (apparently) trust that Hashem would never put us in a difficult position, that Hashem would never expect us to actually have to choose between more than one option in life. If Hashem brought shidduch number one into your life, it is a religious obligation (they claim) to trust that shidduch number two can’t possibly be “the one” as long as shidduch number one is still anywhere in the picture. Why must we believe this? Because it is far more convenient than dealing with an alternative that isn’t black and white, one that demands careful thought, sensitivity to nuance, and the willingness to take charge of one’s life. Bitachon, indeed.

An examination of more concrete Torah sources reveals a different perspective. Many midrashim put forth the idea that Hashem orchestrates shidduchim, at times even against the will of the parties involved (which is apparently the inspiration for many present-day parents and shadchanim). This certainly indicates that one need not try to force the issue when searching for a spouse, but to pursue quality leads in a responsible, sensible manner and trust in divine guidance to bring success. Nowhere in traditional sources is it suggested that one spurn all potential leads because one just spoke on the phone for five minutes with a complete stranger and arranged a meeting with that person. On the contrary, King Shelomo advises us to continually apply effort in different directions, for no one knows which effort will bring success (Koheles 11:6).

The Gemara further informs us that one is permitted to marry a woman on Chol Hamoed, lest someone else preempt him and marry her first (Moed Katan 18B). Aside from the philosophical, bashert issues raised by this, we must wonder where this someone else is coming from. After all, it stands to reason that the man and woman in question had courted prior to Chol Hamoed. Chazal would not institute an exception to the Halachos of Chol Hamoed that they formulated for a case that is theoretical, highly unlikely, or possible only for those who don’t have bitachon or proper middos. Clearly, then, it was acceptable for people – at least women! – to consider more than one person for marriage at a time.

Certainly we must be sensitive to the deeply personal nature of shidduchim, and do our very best not to cause unnecessary hurt to people’s feelings (some degree of hurt, however, is often inevitable). Just as we may not lead someone to believe that we wish to purchase something from them when we are only casually looking around, we must not lead people to believe that we are seriously interested in them when we are not. However, when the relationship is only in the preliminary stages, it should be understood that the only commitment is to proceed on a good-faith basis, and that until both parties agree to “go steady” there is no such obligation.

Those who feel for personal reasons that dating more than one person at a time is inadvisable are free to do what suits them. As a society, however, we must acknowledge that the benefits of comparison-shopping apply no less to shidduchim, and that considering more than one person at a time is likely to help one clarify the qualities that one truly wants and needs in a spouse.

If we proceed in a fashion that is most conducive to success, only then have we earned the right to trust in Hashem to bring us that success. With the many difficulties already facing singles today, let us do away with the unnecessary rules and strictures that only further stand in the way of Hashem’s deliverance.

Chananya Weissman is the founder of EndTheMadness (, a comprehensive campaign to rehabilitate the culture of shidduchim. He can be reached at