As is typical of boys in shidduchim, I had a lot of names thrown at me by shadchanim. I would make the requisite inquiries into each suggestion, get back to the shadchan with a yes if I was interested, and then wait to hear back from the girl.

Most of the time, the answer was no. Actually, most of the time there was no answer — the parents of the girl simply wouldn’t get back to the shadchan. Presumably, they were trying to spare me the disappointment of being rejected, but that left me hanging, waiting for an answer until I couldn’t take the suspense anymore and I picked up the phone to ask the shadchan, “What’s doing?”

Even then, I usually wouldn’t hear a flat-out no. “Oh… I’m not sure… They said she was busy…. They didn’t sound excited….” A frank “they’re not interested” would have stung, but at least the sting would have been brief and unequivocal. Instead, I was left in no-man’s-land, forced to figure out on my own that the answer was no.

When I did get a yes from a girl, the aftermath of the dates was similarly frustrating. It’s always disappointing to be turned down after dating someone, but when a reason is given, it mitigates the pain of rejection somewhat, and gives you an idea of how you can improve yourself going forward.

Shadchanim usually had no answer to the question of “why did the girl say no,” which left me discouraged and mystified as to why I was getting rejected so often and how I could improve my shidduch prospects.

At one point, about ten girls in a row refused to go out with me. Hearing no after no made me realize that even having a job and being koveia ittim weren’t enough to land me a good shidduch. Apparently, I discovered, the shidduch crisis is not so much about quantity as it is about expectations: The fact that good boys are in short supply doesn’t mean that girls have lowered their standards. If a girl is looking to marry a learning boy, she wants someone who’s genuinely committed to full-day learning. And if a girl is looking to marry a working boy, she wants someone who either has a well-paying job or is studying for a respectable degree. No serious girl wants to marry someone who isn’t particularly accomplished and doesn’t know what he’s planning to do with his life. Even if he’s nice, normal, and frum, like me.

Not being a full-time learner, and not having any degree or career path on the horizon, I thought to myself that perhaps I should settle for any girl who would take me as I was, even before I figured out where I was going with my life. When I floated that possibility to a few of my rebbeim, however, they unanimously nixed the idea. “Marriage is not something you go into bedieved,” they all said. “You marry someone you think is ideal for you, not someone you’re willing to settle for.”

What clinched that perspective for me was when I heard it from the rav of my parents’ shul. That shul attracts people who, like my parents, don’t fit in anywhere else, and this rav is the most accepting, nonjudgmental rabbi I know. If anyone would have encouraged me to accept any girl as my wife just because she’s a Jew and beloved by Hashem, he was the one. Yet he, too, was adamant that you absolutely cannot settle in marriage. “It’s not fair to yourself, and it wouldn’t be fair to your wife,” he declared.

If so, I reasoned, I really have to pull myself together and figure out what I want to do in life.

It was time for a big change. I needed a degree, a career plan, and a more polished profile.

Wanting to remain in a sheltered environment, I decided to move from my hometown to New York and attend a frum degree program. But what kind of profession was I going to pursue?

I had always fancied myself doing something exciting for a living, not something staid or typical. Now that it was time to make a career decision, I considered some fashionable yet kosher occupations, but the more I looked into those fields, the shakier they seemed. What did it mean to “go into real estate”? How exactly did you “start your own business”? What made someone “an investor” or “an entrepreneur” or “a consultant”?

Looking around, I saw a lot of single guys who were determined to get rich quick or build themselves a glamorous career. In the process of chasing their pipe dreams, however, they were making themselves less marketable on the shidduch front, because they didn’t project the responsibility, stability, and commitment necessary for a good marriage.

At this point, I asked myself a question: What’s more important to me — marriage or career? The answer, obviously, was marriage. Being under strict instructions not to settle for a marriage partner, I realized that the corollary was that I would have to settle on my career, since I could not afford to jeopardize my marriage prospects by embarking on a glittery but flaky vocation.

I concluded that if I wanted to earn a stable, honest living, the most realistic options for me were — groan — accounting and computer programming. I opted for accounting.

As it turned out, I actually enjoyed accounting. Not only was entering that field the responsible decision, it was also a clear statement of my priorities: getting married is a higher value to me than building a hotshot career.

Until I declared accounting as my major, my references or shadchanim would frequently call me and say, “They’re asking about your long-term plans. What should I tell them?” But after I put accounting on my résumé, I never got that question anymore. More importantly, when the topic came up on dates or at shidduch events, I no longer had to squirm in my seat and mumble something about “figuring it out” or “looking into marketing.”

In addition to regularly updating the credentials on my résumé, I experimented with different references, shuffling through my roster of contacts and seeing which friends, rebbeim, and family references were most effective. Early on, I naively thought that any good friend of mine would give good information about me, but after hearing several times from shadchanim that the other side was concerned, or said no, because of a silly comment a friend of mine had made, I realized that I needed to pick references who would give the right kind of information.

While my rebbeim had urged me not to settle in a shidduch, it was my friend Asher who helped me to understand what “not settling” actually means.

Asher’s mother is a shadchan, and the first time he invited me over to his house for a Friday night meal, the topic of conversation invariably turned to shidduchim. His mother threw out a couple of suggestions for me, but the girls she described did not sound particularly interesting. Then, her eyes lit up. “I have an amazing girl in mind for you,” she said. She went on to describe a girl who sounded incredible — wonderful middos, bright, talented, great personality, superb family, and, of course, beautiful. Then she paused.

“Here’s the thing,” she said. “The girl was previously married, for a very short time.

“The marriage was a total mistake,” she hurried to add. “And the problem that caused the divorce had nothing to do with her.”

If I had started to feel excited when hearing her initial description of this girl, upon hearing that she was divorced, my interest evaporated.

“I can’t go out with a girl who’s divorced,” I said flatly.

“Why not?” Asher asked. “I went out with her. It didn’t work out, but I was okay with the shidduch in theory.”

I was flabbergasted. “Why would you say yes to a girl like that?” I wondered. “You were never married before!”

He shrugged. “What difference does it make if she was divorced, if the divorce wasn’t her fault?”

I couldn’t believe how little he cared. “Give me some time to digest this,” I said.

After thinking about it for a couple of weeks, I called Asher’s mother with a few questions. “You know what?” I said, after she answered my questions. “I’ll give it a try.”

I never did go out with the divorced girl, because she said no to me — apparently because I wasn’t from New York and wasn’t planning to live there. But just agreeing to date her proved to be a watershed moment for me. I had overcome significant discomfort in agreeing to a shidduch, and had moved from feeling that I couldn’t possibly marry a girl with a certain issue to viewing that same issue as irrelevant.

It dawned on me then that there are two types of issues in shidduchim: issues that can affect a future marriage, and issues that are essentially extraneous and don’t have to matter — if you can muster the maturity and flexibility to look past them.

When my rebbeim had instructed me not to settle in a shidduch, what they meant was that I shouldn’t compromise on the things that are truly important — values, hashkafah, character, compatibility, chemistry. But I understood now that they did not mean that I shouldn’t stretch myself out of my comfort zone and date girls who had some kind of “flaw.”

From then, I started saying yes to girls who were older than I was — something that I had previously not been willing to consider. I also went out with a few girls who were taller than I was — another previous sticking point. When girls who had an unusual family background, or were divorced, were redt to me, I did not immediately say no, but rather looked carefully into the circumstances and made a case-by-case decision.

My newfound ability to propel myself past my initial discomfort with a particular issue made me feel greatly empowered, because now I had many more options in shidduchim. Unfortunately, I discovered that many people were a lot less willing to overlook the issues that I had learned to recognize as trivial.

When I was 26, a shidduch was suggested for me with a girl who was 29. I needn’t have worried about the significant age gap, because she turned me down without making a single phone call; just glancing at my résumé convinced her that I was “not heimish enough.” Another family that had one child on the streets and another child with severe learning disabilities said no to me because my family was “strange” — even though their daughter was in her late twenties.

Once, I was talking to a single friend, and he confided that he had met a girl he was very interested in marrying, but he couldn’t bring himself to pursue the shidduch because the girl was two years older than he was.

“I just went out with a girl who is four years older than I am and two inches taller,” I countered. “Plus, she’s a baalas teshuvah.”

He was floored. But he still couldn’t bring himself to marry this “older” girl, even though he really liked her. By this time, he had been in the parshah for close to a decade and had spent tens of thousands of dollars on dates. (He told me he had done the math.)

After several years in shidduchim, I was feeling very discouraged. At that point I began talking to a dating coach, who helped me bear the load by hearing me out when I was frustrated and helping me vet shidduch candidates more effectively. When I was considering meeting a girl who had some significant baggage, for instance, she made some inquiries herself and advised me to stay far away.

But when I told my friends that I was working with a dating coach, many of them scoffed at me. “What’s the point of a dating coach?” they said. “It’s a waste of money.”

A friend of mine had a pattern of breaking up with girls and then regretting having broken up. In general, I noticed that he made decisions very impulsively, so I suggested to him that he talk to my dating coach. “I don’t need a therapist,” he said pointedly.

When I tried explaining that a dating coach isn’t a therapist, I got nowhere.

He wasn’t the only single I encountered who was unwittingly sabotaging his own shidduch prospects.

At one point, I attended a networking meeting for singles at which each of the 20 singles in attendance was asked to describe what they were looking for in a shidduch. After hearing one person after another describe themselves in vague terms and say that they were just looking for a nice guy or a nice girl, one of the shadchanim coordinating the event stood up and requested that people be more specific. “It’s not enough to say that you’re looking for a nice person,” she emphasized.

Sure enough, when the next girl got up and described what she wanted in a shidduch, she said, “I’m, uh, just looking for a nice guy.”

I, for one, had come to the meeting prepared with a short but detailed description of what I wanted in a wife. “I need a girl who is frum and smart and has depth, but who is easygoing and openminded enough to give me the space to be who I am and do the things I want to do,” I explained. “And it’s really important to me that she be a happy person who can roll with the punches.”

But few of the other singles in attendance — all of whom had been in shidduchim for several years — could articulate a similar vision for what they were seeking in a spouse.

The people at this meeting reminded me of my teammates back in high school who had stood in place on the basketball court waiting for the ball to land in their hands. Had Coach Mullen been at this meeting, I thought, I’m sure he would have slammed down his clipboard in frustration.

At another shidduch event I attended, I met a girl I thought I would want to date, and I asked the shadchan in charge to set me up with her.

“You want to go out with her?” the shachan asked, raising an eyebrow. “I don’t know… I mean, I’m looking at your résumé, and I see you attended two different high schools. You learned in the Mir, but not by Rav Asher. And you’re in a no-name college. This girl is from a very prominent family and has a prestigious degree and career. She’s not going to be interested.”

After that experience, I mentally added “humble” to the list of qualities I was seeking in a wife. A girl who would judge me by the types of schools I attended and evaluate me in terms of superficial prestige was automatically disqualified, in my eyes, due to her attitude of entitlement.

That realization turned out to be the perfect prelude to my own shidduch, which materialized shortly thereafter. When my kallah, Chedvah, was first suggested to me, I almost nixed the idea. She was described as quiet and eidel, while I thought I needed a girl who was vivacious and outgoing, because I had met a number of “quiet” girls and found that I didn’t click with them. And not only were her parents divorced, but her family situation was so complicated that it made my family look positively mainstream by comparison.

My dating coach encouraged me to give it a try, though. “The fundamentals are there,” she noted. “She has the qualities you’re looking for.”

To my surprise, when I was with Chedvah I didn’t find myself struggling to fill the awkward silences, as had often happened to me on previous dates. She had plenty to say, and the conversation flowed easily. We felt comfortable enough with each other that by the fourth date we were already discussing our complicated family lives, and I was very impressed by how calm and pragmatic she was about her background. Nor did she care that I was “just” becoming an accountant, or that I wasn’t attending a brand-name college.

Still, I was nervous, especially because I had expected to marry a spunkier, more outgoing girl. It took time and some adjustment of expectations on my part — with the help and guidance of my mentors — before I could bring myself to close the shidduch. “Those cool, edgy, spunky girls you’re talking about might make great dates,” one of my rebbeim noted, “but they won’t necessarily make a good wife.”

Our engagement was, in a sense, the culmination of every lesson I had learned during my five years in the parshah. It was my dating coach who helped me look back and see how all the work I had done on myself had prepared me to feel confident that Chedvah was the right one.

“You were honest with yourself about who you are,” she began. “You moved to New York and made yourself presentable with a job and education. You were willing to stretch yourself and overlook some of the things about Chedvah’s family and personality that made you uncomfortable. And you knew what was important to you in a shidduch, so when you met Chedvah, you were able to mentally check off the qualities that you were looking for while ascertaining that you clicked with her.”

I don’t think it’s my efforts that got me to where I am; shidduchim are made in Heaven, and if a person manages to get engaged, it’s purely by the grace of G-d. I davened my heart out during my years in shidduchim, and I know that tefillah is the most potent tool of all. Yet I also believe that had I stood passively and waited for the right shidduch to materialize, I might just be standing around still wringing my hands about how “the system is broken.”

People like to talk about how pictures are the problem, or résumés are the problem, or shadchanim are the problem, and so on. The assumption is that we are all victims of “the system,” and if only it would be “fixed,” the shidduch crisis would disappear.

Having spent five years in the “system,” I honestly don’t think it needs fixing. We already have shidduch websites, speed-dating events, singles retreats, and a mindboggling number of official and unofficial shadchanim working valiantly to set people up.

But I don’t think we spend enough time addressing the main issue: the people within the system. No change to the system will help if singles are not willing to look honestly at who they really are, build themselves up, narrow down their needs, and push the boundaries of their comfort zones.

Does doing all that guarantee you a shidduch? Of course not. But going after the ball rather than standing by and waiting for it to land in your hands makes you a lot more likely to reach your goal.

Postscript

Chedvah and I got engaged just before the COVID-19 outbreak. For many engaged couples, the derailment of wedding plans caused by social-distancing regulations has been devastating. For me, however, the new configuration of what a normal, frum wedding looks like has been a huge relief, because frankly, I wouldn’t even want to have a regular big wedding. My kallah and I both have unusual family situations, and it would be very uncomfortable for both of us to have our families showcased before hundreds of people, many of whom don’t know much about our backgrounds and would find the cast of characters in our family quite odd. I’m also not a great dancer, so I’m grateful to be spared the prospect of having to spend hours at the center of a dance floor.

Chedvah, eidel girl that she is, is equally delighted to get married surrounded by only a few close people. And the negligible cost of the tiny backyard wedding we’re planning takes a huge financial burden off our shoulders and those of our parents.

Were it not for this catastrophic pandemic, we would never have dared buck societal norms by planning such an unconventional wedding, but for us the opportunity to celebrate our chasunah out of the limelight is a silver lining in what is otherwise a very dark cloud.

(Originally featured in Mishpacha, Issue 811)