We take for granted that trying to help singles marry is a mitzvah. What most people don’t seem to account for is the fact that, like all mitzvos, there are parameters that define what constitutes performing the mitzvah properly and what can actually be a sin — even if one’s heart is in the right place.

If one offers a sacrifice in the Bais Hamikdash he is performing a mitzvah. If one offers the same sacrifice with the same pure intentions outside the Bais Hamikdash he commits a grave offense. Similarly, one can attempt to arrange a shidduch and be performing a mitzvah, but one can also be committing a terrible sin that far outweighs his good intentions.

The ways in which our community sins against singles are many and widespread. Because these sins are easily camouflaged as mitzvos, and because there are so many nuances and subtleties involved with helping singles, it is extremely difficult for many people to recognize that they may be sinning. It is all too easy for one to rationalize his behavior, especially when societal norms favor “helping” singles in ways that are not appropriate.

I will provide common examples of this to help educate the community and with hopes that those who are well-meaning will try to refine the manner in which they try to help singles. In addition, some people will hopefully realize that this mitzvah is not for them, just as not all mitzvos are intended to be performed by all people at all times. Some people may not yet be equipped to perform the mitzvah, and others would be best off avoiding it altogether.

I. Individuals

Well-meaning individuals sin against singles with speech and action. They sin with speech by making a variety of inappropriate comments, such as the following common examples:

“Why aren’t you married yet?” This generally comes from people who are favorably impressed with a single they don’t know very well. It is intended as a compliment, as if to say “You’re so terrific I can’t believe no one snapped you up!” While masquerading as a mitzvah by supposedly complimenting the single and boosting his self-esteem, it only draws attention to the fact that he is still single and puts him on the spot. After all, how exactly is a person supposed to respond to this? “Yes, I’m wonderful, and I also can’t believe no one wants to marry me.” This doesn’t exactly brighten a person’s day.

Sometimes the same question is asked, but as a genuine inquiry. The questioner wants to help; he wants to know what’s holding the single back from getting married so he can try to fix the problem. Needless to say, despite the good intentions, the question is entirely tactless and bound to be hurtful.

Furthermore, the question presupposes that there is a clear reason why one person may have been fortunate to find the right person and get married while the next person has not been so fortunate. That is far from true. Most singles don’t need to be fixed before they are marriageable, and plenty of married people have tremendous problems and issues that may make their relationships very unpleasant. If things worked out a little differently, plenty of singles would be married and plenty of married people would still be single. Hence, to presuppose that there is a “reason” why someone is single is very shortsighted and even insulting.

Besides, even if there is a reason why someone is single, what makes anyone so sure he is able to help or that it is even his business?

“This is why you aren’t married.” This is an incredibly presumptuous and offensive comment that is nevertheless quite common. It is never appropriate for anyone to say this to someone. Never.

Unless one is a prophet he cannot possibly know why anyone else is not married, does not have children, or is otherwise not blessed in a certain fashion. The best anyone can manage is an educated guess, and even this should only be ventured with humility and sensitivity if the relationship with the other person and the situation call for it. The above declaration is just the opposite; it is arrogant, insensitive, and will only hurt, not illuminate. Generally people will make this remark to lash out at a single and strike at a raw nerve, not to direct him on a productive path. They will rationalize otherwise, but this comment can never be rationalized.

“Im Yirtzeh Hashem by you!” Singles often bristle at this remark, which tends to come from people on the fringes of their life — if even that close — and only draws attention to their single status. Personal remarks by people on the fringes of someone’s life are generally not appropriate, even if well-intentioned.

At one memorable wedding a distant cousin who has no relationship with me advised me, with barely a hello, to get to know a certain man, since his wife is a shadchan. (I should have recommended an etiquette specialist for her, but refrained.) A stranger approached me and pronounced “Speedily! Speedily!” (I wished the same for him, though we probably had different things in mind.) Yet another distant acquaintance sat down next to me and asked me straight off what hishtadlus I was doing. (My response: “None of your business.”)

Unless it is appropriate for fringe acquaintances and strangers to make similar well-intentioned comments to childless couples, the severely ill, or those in dire economic straits, it is not appropriate to make such comments to singles about their personal status. A little tact means more than a perfunctory blessing.

Rabbis and other people of influence should be especially careful before speaking about these issues. Much of what is said by such people is terribly misguided and uninformed, and the damage from these remarks can be tremendous and difficult to undo. True leaders know their limitations and don’t tread in areas outside their expertise without due diligence.

Individuals sin against singles through action primarily in three ways. The first is by setting them up in negligent fashion. It is not a mitzvah to set two people up on a whim with the rationalization that “it’s only a date”, “you never know”, or “you can’t leave a stone unturned”. Save the flippant attitude for your own shidduch search if you really believe in it, and show a little more concern for the welfare of others.

Bad experiences, and even a series of neutral but unsuccessful experiences, can take a lot out of a person, and many such experiences can be avoided by doing just a little homework. I am against the Secret Service-like investigations common in some circles, but one should take setting people up seriously enough to get their facts straight and put some serious thought into the matter. Ask the right questions, pay attention to the answers, and never lose sight of what the other person is going through. Fail to do so, and it’s a sin at worst, and a severely blemished mitzvah at best. Even if it works out, it’s in spite of the effort, not because of it.

Individuals sin against singles by broaching the idea of setting them up and then failing to follow through. It’s startling how common this is, and completely inexcusable. Don’t start something you aren’t committed to seeing through.

Individuals also sin against singles by disparaging their ability to make proper decisions for themselves. There is a fine line between offering well-timed advice and meddling too closely in someone’s personal affairs, and many people don’t even recognize that such a line exists when it comes to singles. If someone decides not to pursue a relationship with someone, for example, his decision should be respected, not become the basis for critical remarks.

A single should never be made to feel like a chessed project or a lesser person. One who sets singles up without showing them the same respect and regard they would show a married adult is certain to sin numerously against them. I would advise such people to find a different, safer mitzvah with which to occupy themselves, and to leave this one to people with more refined character and interpersonal skills.

II. The Community

The community at large sins against singles in a variety of ways. This “crisis” didn’t just appear out of thin air, after all. Our community has gone off track, and unless it seriously changes course the problems will only continue.

The community sins against singles first and foremost by trivializing the problem. There is no one “problem”, such as “singles are too picky”, “there aren’t enough men” or everyone’s favorite scapegoat, “television”, that is responsible for a culture that makes dating and marriage so difficult. To trivialize the problem is to ignore the real issues, and to ignore the real issues is to sin against singles.

Singles tend to be more transient, and thus more commonly find themselves the new person in town — without the built-in companionship and social entry of a spouse. It is incumbent on every shul to have some sort of welcoming committee or similar mechanism to help new people feel at home and become integrated into the community. Singles don’t necessarily need meals or shidduch dates, but they need to feel like a valued member of the community. Singles flee to places like the Upper West Side — no great sanctuary in its own right — because they are often made to feel unwelcome and disregarded in more family-oriented communities. This has to change.

The community sins against singles by closing off natural meeting opportunities such as wedding meals, concerts, and other events that have no compelling reason to fence men and women off from one another. We do not have a crisis of Jews acting inappropriately at these events, so these suffocating, unnecessary strictures that only create other problems must be removed.

The community sins against singles by substituting natural meeting opportunities with all manner of degrading, inefficient, and generally ineffective consolation prizes. We don’t let singles meet one another at the wedding, but we console them that maybe someone will take pity on them and set them up. No deal. We replace non-pressurized events with events that have married chaperones, shadchanim, and “facilitators”, lest singles talk to one another instead. Not good enough. We create dating events that resemble bad game shows and offer singles icebreakers suitable for small children to help lessen the pressure and awkwardness. Just not smart thinking.

The community sins against singles by driving them away from an observant lifestyle. I personally have encountered more than a few people who drifted away from observance because they felt they had to choose between being observant — shidduch system and all — and ever getting married. No one should ever have to make such a choice.

The community sins against singles by repackaging the same failed ideas in different wrapping paper and presenting it as something exciting. Prior generations did not know of a crisis of this nature, so we should look to them for guidance instead of pretending it was always done this way or, worse, claiming it has to continue to be this way. Nonsense. Things had to change to become like this, and they can just as easily change again — this time for the better.

III. Singles

Singles sin against themselves as well. They sin against themselves by allowing themselves to be degraded and mistreated because they are afraid of being stigmatized. They sin against themselves by doing all manner of things that aren’t true to themselves “for shidduch purposes”, as if they wish to marry someone who doesn’t appreciate them for who they really are. They sin against themselves by never developing a true sense of self and a sensible derech that they can stick with instead of changing things just for the sake of changing.

Singles sin against themselves by failing to take charge of their personal lives, and instead waiting for others to do things for them. If the events out there are not to your liking, organize your own. If the community isn’t working for you, then work to change the community. If you see someone interesting, strike up a conversation with that person. If you had a good time on the date, ask that person out again, directly. It is normal to reject and to be rejected. It is not normal to have a third-party do the real communicating for you.

Singles sin against themselves by substituting real hishtadlus with praying in cemeteries, adopting strange pseudo-religious customs, and trying far-fetched, painful things like degrading singles events. Acts of desperation such as these are not hishtadlus; quite the reverse, in fact. True hishtadlus is taking normal, sensible measures to attain a goal while putting one’s trust in Hashem.

I am optimistic that things really can change for the better. But it won’t happen by itself or through an act of God. It will only happen when singles, married people, and the community at large face up to the real issues and commit to meaningful changes. It can happen. It starts with you.

That’s a mitzvah.