2021 One Year of Shidduchim Part 1
Chananya Weissman
Story begins in 2016, posted on July 20, 2021

As promised, after many years I am sharing this publicly.  When you read this, please resist the urge to react like one of those judges on a tribunal.  This isn't about me.  Just read, listen, and reflect.

One Year of Shidduchim

One fall evening a couple of years ago I went out with a girl for a second time. There was nothing remarkable about it. We had good conversations, but I was not attracted to her and our lives did not seem to be heading in compatible directions. I was willing to see her again. She did not want to continue dating, but was willing to stay in touch as "friends". I told her I had friends already, I was looking for a wife, and that I was not interested in being friends with women. That was the end of that. No great loss.

In the nearly two years since then, that is the closest I came to getting married. In fact, it is the last time I went out on more than a blind date with anyone.

Several years ago I reached the age when it was considered inexcusable for me to still be single. Prior to that, it was more common for people to offer glib, optimistic reasons for my bachelorhood. I was still a "baby". My future wife was still too young. It was only a matter of time until I met the right one. There was plenty of criticism and armchair-quarterbacking, of course, but generally speaking the former was mild and the latter benign.

One fine day (I forget exactly when) everything changed. I was no longer a baby, but a past-his-prime single. My future wife was most definitely of legal age, and there was no excuse for my not having wed her. It was no longer a matter of time until I met her doing what I was already doing; everything I had done was clearly wrong, and I would be doomed forever unless there were fundamental changes.

Like some foreboding Midrash about Judgment Day, my supporting angels all turned into prosecutors. Anything I said would be used against me in a court of law, and the mere fact that I defended myself from a relentless onslaught of personal criticism was proof that I was stubborn, inflexible, unwilling to take advice, and in need of serious intervention. Only an admission of guilt and severe personal failure would be accepted. The verdict was in before the trial began. I was single past an acceptable age. Either I was doing everything wrong or there was something seriously wrong with me. Case closed.

I was supposed to accept a plea bargain. I would have to accept coaching, mentoring, or actual therapy to determine what was wrong with me that I couldn't get married. I would have to be willing to change anything and everything about myself, and humbly accept personal advice from anyone and everyone so long as they were married (that fact alone rendered them experts on why I wasn't married and what I needed to do about it). All of my decisions that impacted my search for a wife would have to be approved by a married supervisor.

In exchange, I would be allowed to remain in the good graces of the married community, as a single under rehabilitation, and if I ever got married they would take full credit for it. After all, I couldn't possibly have done it without their intervention. Had I been able to, I would have done it already.

The court considered this a most generous offer in fact, the only sensible option for me and fully expected me to accept it with tremendous gratitude, as most singles do. Once the rehabilitation period was over, and I was married, I would even be promoted to a position on the court, and allowed to judge other singles.

In defiance of all those urging me to accept this offer and begin the rehabilitation process, I rejected the plea bargain and loudly proclaimed my innocence of all charges. The court erupted with a mixture of shock, outrage, and derision. The whole world knew I was guilty. My age and marital status alone proved that beyond a shadow of a doubt. Who was I kidding? What did I hope to accomplish? Those who had previously suggested mere coaching would be sufficient for me now conceded that full therapy was needed. Clearly I was insane.

The official verdict states that I do not really want to get married; I am too picky; I turn people down too quickly; I turn people off right away; I don't know how to make a good impression; I am angry; I am bitter; I am scared to get married; I met the right person and missed the boat; I am closed-minded; I don't listen to people; I am in flagrant violation of the obligation to get married; I am not trying hard enough; I don't let people help me; I am my own worst enemy.

(Other than that, I'm a great guy, and any girl would be lucky to marry me.)

The court of public opinion long ago banished me to solitary confinement, as a single who refuses to accept rehabilitation and lives in contempt of the court. This verdict cannot be appealed. The only way out is to surrender to the court and beg for help.

I am now officially an "older single". I would no longer be welcome at most singles events (not that I would go anyway) because I would be considered a creepy old man, and the younger women would be uncomfortable with me there.

No one believes anymore that my approach to dating is correct or that the only thing holding me back from getting married is the misfortune of not having met my future wife, through no fault of my own. It is assumed that I must have had plenty of great opportunities and squandered them, with no evidence to support that other than my age. No other evidence is needed. It simply must have happened that way.

Younger single relatives will not consult with me regarding issues and challenges they are facing in their own searches. My many years of experience as a single are of no value to them. I can't possibly have learned anything, there is no advice I can offer them, and I am not even worth being a listening ear. Since I am not married, I must be utterly clueless. Only married people even those who don't remember what it was like to be single, even those who never really experienced it altogether have anything to say worth listening to.

I have reached the point where if I were to inform people that I was getting married, they would be extremely surprised. No one actually expects it to happen. They hope, but they don't expect it. They urge me not to give up, but on a certain level, they already have.

I believe as strongly as ever that my approach to dating is correct, and if I could do it over again I struggle to think of anything significant I would have done differently. I can think of no obvious mistakes, no golden opportunities that I squandered, nothing that I clearly should have done differently.

This is not to say that I believe I am perfect and that I made no mistakes in more than fifteen years of dating (or not dating, as it mostly was). It is to say that I believe to the core of my being that I conducted myself in an entirely reasonable and appropriate fashion, with a healthy outlook and more than enough effort to be successful. My approach could very plausibly have led to meeting someone compatible and getting married. It just didn't happen.

Had I gotten married before it became inexcusable to be single, no one would have been surprised. No one would have said, "I can't believe he got married with his illogical approach, backwards behavior, and severe personal flaws." But once I went from being a "baby" to being "old" in that fateful instant (whenever that was) the reason for my singledom immediately and unequivocally became my illogical approach, backwards behavior, and severe personal flaws. Just like that, it went from being "only a matter of time" to serving time. Yesterday I was fine; today only therapy and a complete overhaul could save me. There was nothing in between.

I will concede that it is natural to question someone with an obvious shortcoming in areas of human achievement that we consider "normal". If someone is unable to obtain "respectable" employment for a long period of time, we lose respect for the person. If someone's income is lower class, we consider the person low-class. And if someone remains single past a certain age, we assume this person is not marriageable as they currently are and as they are currently conducting themselves.

At the same time, we have respect for people with impressive careers, even though we know that most of these people are no more qualified than those beneath them (the best proof being that they are easily replaced); even though we know that many of these people were given opportunities that they didn't necessarily "deserve", and that could easily have been given to someone else; even though we know that had things turned out slightly differently, these people would be nobodies.

Similarly, we consider people with lots of money to be successful even if they obtained the money mostly through good fortune and lucky breaks, even if they are miserable human beings, even if every time they open their mouth something foolish comes out. We don't stop to wonder why we equate wealth with intelligence, or why the world is full of brilliant, hard-working people who don't make a great living, yet no one wants to meet them or hear them speak, let alone pay money for the privilege, while we are eager to listen to empty, boring speeches from wealthy executives, clinging to the wistful hope that we will somehow glean their "secret". They have no secret. In ten years many of these people won't be wealthy, either. Yet still we believe, and still we worship.

Similarly, we don't ask ourselves how it can be that everyone who is married figured out the amorphous secret to getting married, while everyone who is single has no clue. We don't ask ourselves why in ten years many of these wise married people will be single again, while some of these clueless singles will be married, and how this role reversal of knowledge and ignorance will have occurred. We don't ask ourselves why we cannot look at a graduating class of high school students and predict with any confidence, let alone accuracy, who will marry soon, who will marry successfully, who will marry late, and who might never marry at all. If the flaws of older singles are so many, so fundamental, and so pronounced, how can it be that no one is concerned about them, or even recognizes them, until they are already older singles?

The greatest lie man tells himself is that he is truly in control of his destiny. If we were to allow ourselves to believe that someone can do everything right and still be out of work, poor, single, or unfortunate in any other area of life, then we would be forced to admit that we cannot take credit for our own good fortune. We didn't get that job because we were smarter, tried harder, and worked better than the next candidate. We don't have money because we know how to make money. And we didn't get married because we are so charming and intelligent.

We might have done some things right, sure. And it's always a good idea to be responsible. But at the root of it all, we were blessed, it was given to us, and we can just as easily lose it all, no matter what we do. We're not that smart, and we're not in control.

No one wants to believe that. So we look down on unfortunate people and we send singles for therapy. It helps feed the lie that we can explain why people have what they have and lack what they lack. And, just as importantly, those who are more fortunate can feel that they are better and smarter.


All the preceding was a long introduction.

I have prepared a catalog of nearly a full year in the life of a single: not just every date (of which there were only two ill-advised blind meetings), but every "opportunity" that was presented, as well as some of the more noteworthy "suggestions" and advice that were offered during this time.

A year is a very meaningful sample size. We would not bless a single that in the next day or week he should meet the right person, but it is common for singles to be blessed that "by this time next year" it will have happened. Why not by this time next week, or even next month? Because secretly we all understand that there is no formula for meeting the right person, and only something completely beyond our control can bring about this good fortune. A year is a long enough period of time that we are willing to allow for such a metaphysical event to occur.

This is also why all the charlatans who make a business out of saving singles typically allow a year or so for their magic to work. They have to allow themselves a comfortable buffer for this event outside their control to occur, and then they can take credit for "the change" that made it possible. If they promised faster results they would be proven liars far too often to stay in business. Those who sell false hope never promise fast results, and they never offer refunds.

We can agree that it would be unreasonable to expect any single to meet the right person on any given day, no matter what, and it would therefore be unreasonable to blame a single for not meeting the right person on any given day. Well, what if the single had 365 such days in a row? Is the single any more blameworthy? If there is a certain period of time when it becomes fair to blame someone for not having met the right person, what is this period of time, and why is it exactly that amount of time? Whatever the cutoff point is, why not a little more or a little less? And what is supposed to be different about this extra time that pushes the single into blameworthy territory? Because "there must have been" a good opportunity during this time? Says who?

We also believe that on Rosh Hashana, God decides a person's fortune for the coming year. Presumably this includes such a life-altering variable as meeting a potential spouse. If God decided that a particular single will not meet a potential spouse in the coming year nothing even close then how can we blame the single for not meeting such a person? How can we insist the single needs therapy and to change his entire approach if he simply didn't have the right opportunity? On what basis are we making this severe diagnosis if we are not absolutely sure that God said yes and the single blew it? And if we DO believe it is in the hands of the single to find such a person on his own, what is God really deciding? Merely to play along?

With this in mind questions that I am willing to bet you never seriously considered I present the hand I was dealt since last Rosh Hashana, which is nearly an entire year ago. As I mentioned before, there were only two actual meetings during this time, both of which were ill-conceived and beyond far-fetched. Despite this, it was actually a busier year than most, with numerous "feelers" and "opportunities", which I generally refer to as background noise.

The critics will insist that buried within this catalog might have been one or more golden opportunities that I missed, but I would advise them not to judge. Others would advise a single to go full force after every "opportunity", no matter how far-fetched it seems, but that will only drive a person crazy and lead to a genuine need for therapy. The goal in sharing this is to encourage people to be more reasonable and understanding in favor of such senseless, thoughtless advice.

A few other points to keep in mind:

The events listed below are not necessarily in chronological order.

I am not interested in blaming anyone for my situation, particularly those people who genuinely care and have made a real effort to help. That said, in some cases these efforts were off track, and I hope they will learn to refine their ways. If singles are having a hard time, they may well need to refine their ways, but those responsible for their opportunities surely need to do the same.

I am not interested in embarrassing anyone, and have left out details that might identify people. If you recognize yourself, don't take it personally. I'm not writing this to give you mussar. If I am sharing this with you, it's only because I like you and am glad to have you in my life. I'm simply sharing a catalog of the last year, and you happen to be part of it.

Without further ado. (Continue to Part 2.)