If At First You Don’t Succeed – The Saga of an Unstoppable Shadchan

By: Sara Lehmann

An Addiction to Shidduchim

At any given time, I can be found trying to make shidduchim. The operative word here is “trying.” Because while I continually set people up on dates and they continually go out, I have yet to make an actual shidduch. Indeed, I often feel compelled to put in a disclaimer at the onset of putting together a match by telling both sides that, while I succeed in having ideas for compatibility, I have not yet succeeded in making it to the finish line.

Some of my family and friends tell me that I shouldn’t jeopardize my standing as a so-called amateur shadchan by publicizing my failure. But aside from being honest, downplaying my success rate (or lack thereof) is an insurance policy against disappointment when that inevitable flop materializes. Minimizing expectations has a way of cushioning the almost predictable bust.

With the exception of two of what I call “half-shidduchim,” in which I was instrumental in bringing one half of a couple to his zivug through previous efforts on his behalf, I have spent the better part of 20 years trying to make matches to no avail. My initial involvement began with a family member, but it quickly spread to the most random of people.

My ideas are not off the mark; people tell me they are usually quite good. Often, my suggestions are validated when I present them and hear that they have already been tried. And many times, I’ve had people go out, some for prolonged periods. I have set up couples who have met eight, ten, fourteen times. And then, for various reasons, the shidduch falls apart.

I frequently hear platitudes from others when they hear of my thwarted efforts: “You’re bringing singles one step closer to their basherter,” “It’s the thought that counts,” and “You’re giving singles hope and chizuk.” While I appreciate these well-intentioned clichés, they are not what keep me going. I must admit that I have an addiction to shidduchim. I cannot meet a single without immediately trying to think of someone to fix him or her up with.

My desire to help, however, has not yielded success, and I long to lay claim to at least one, to instill in others more confidence in my abilities. Perhaps I should be more of the pushy shadchan. Or perhaps I should subscribe to the “you never know” party line of shadchanim and put less thought and nuance into my ideas. Or maybe, because of the enormous amount of time and energy that I invest in the process, I should find another chessed.

Surprisingly, I still get excited with my ideas and maintain a flicker of hope that they might actually work. At times, I need to temper my enthusiasm, which fluctuates with every up and down of the shidduch process. But I am not delusional; I am just not ready to give up.

I actively worked at shidduchim while my children were young, but now that some of them have already been or currently are in shidduchim themselves, I can identify even more with the gratitude of those on the receiving end. I am even beginning to believe some of the clichés I so cavalierly dismissed before. Working on behalf of a single does give that single and his or her family chizuk. And “being in the parashah” has also given me, as a wannabe shadchan, immeasurable insights into the tricks of the trade. But apparently not immeasurable enough.

A Family Calling

My inexplicable zeal has trickled down to my own children. Family get-togethers frequently turn into ad hoc shidduch meetings, each participant bringing new names and suggestions. One of my children has moved beyond brainstorming to actually planning formal shidduch meetings and events.

But my married daughter, who draws on her husband’s connections in addition to her own, worries that my “condition” might be hereditary. Four years of efforts on her part have also yielded many dates, much eagerness and angst, but no walks down the aisle.

Like mother, like daughter. We often commiserate about our letdowns and joke about coming up with “bad ideas” in the hope that those might work out. My daughter also questions whether a more aggressive approach on her part might yield better results. “I can definitely be pushier,” she tells me. “I’m good at following up, and if I were more aggressive I might get more initial yesses from some boys.”

She laments what she sees as the overinvolvement of parents, especially of singles already in their mid-to-late twenties, which she feels might possibly impede their children’s chances. “I think one of the challenges is dealing with parents,” she tells me. “They often want different things than their children. Older singles especially should be more involved and show more initiative.”

My daughter says she shares my addiction, but hopes she won’t share my track record. “I’m hoping not to follow in your path,” she says facetiously. Involvement in shidduchim can often be a full-time job and my daughter might get frustrated at times, especially if she’s heavily invested in a particular dating episode that ends unsuccessfully or thinks of multiple ideas only to discover they were already presented. However, she tries not to get disheartened or to take things personally.

“It’s so rewarding to work with people,” she tells me. “Some of them are so grateful. If I have a good idea I’m not going to say, ‘Why bother if nothing has worked out in the past?’ I’ll still keep trying.”

A Labor of Love

If misery loves company, I can draw further consolation from my close friend Ora K. Like me, she has been working on shidduchim for years without having made one. Yet Mrs. K. remains undaunted. She shies away from referring to herself as a shadchan and finds that people are happier that way. “I tell people I’m not a professional shadchan; I dabble. I like to help people and do it for so many of my friends. It’s a labor of love. And because I care about them, they know I do it with their best interests in mind.”

Mrs. K. initially became involved in shidduchim when her own children were in the parashah. She tried setting up boys whom her girls had dated. “When my daughters were dating and one dated a guy who wasn’t for them, I would look to see who he would be good for. I also have a younger sister who got married later and that certainly showed me how difficult shidduchim can be. It definitely made me more sensitive.”

I ask Mrs. K. if she gets frustrated after putting in so many years of efforts without concrete results. She tells me “frustration” is the wrong word. “It’s disappointment. Look, I’m disappointed after having had three shidduchim go out in the past week and none got past the first date.”

Apparently, she does not allow her disappointment to overly upset her and deals with it by occasionally taking a break. “I take a day or two off, a breather,” she says. “But somehow it pulls you right back in, because if you want to help people then you have to keep on going.”

Mrs. K. looks at her role as that of a “marriage broker.” And when I question if there’s anything she thinks she could do differently that might allow her to succeed, she replies, “Hakol biyedei Shamayim. You do your best but, bottom line is, we’re all just shluchim.

She also points to the astonishing amount of time it takes to redt shidduchim and get them off the ground. This has even prompted her husband to recently say that he never understood the Midrash that says, “What is Hashem doing since creating heaven and earth…He is sitting and making shidduchim” (Bereishis Rabbah 68:4), until he saw Mrs. K. spending days and nights on them.

Shadchan Success Stories

And then there are those I am in awe of – those shadchanim with so many shidduchim under their belts that it is hard for them to fathom my lack of a single one. Lisa Elefant, a well-known Brooklyn shadchanis and the founder of the shidduch initiative Adopt a Shadchan (AAS), is incredulous when I describe both my “addiction” and my lack of success. “Honestly,” she says, “I’m amazed that there are people like you doing it for so many years.” And my perseverance without any triumph convinces her that my “reasons must be pure.” (Phew!)

Mrs. Elefant counsels that eventually persistence does pay off. “What you see every day is that we do not know who the shaliach is going to be. But if you’re making quality suggestions and you’re getting people out on dates, that’s a success, because you’re getting the person closer to his or her basherter. I am sure there are many shidduchim that happened possibly and probably through your efforts, like if you set up a boy and he didn’t think it was for him and recommended the girl to a friend. You don’t know what your efforts will yield.”

She cautions against putting too much of an emphasis on numbers. “People will ask how many shidduchim you’ve made. It’s not about numbers, because even the most successful shadchan can go a few months without making any. And then there are certain months when you’ll have many. But you can’t just say, ‘I’m done, I’ve tried this; I’ve been doing it for six months, a year, and nothing happened.’ You really have to just persist.”

However, Mrs. Elefant is realistic. If someone is not suited for the position and “has been doing this for x number of years and hasn’t gotten any dates, she should probably find some other form of chessed to do.” But like those who highlight the chizuk aspect, Mrs. Elefant stresses that being involved in shidduchim, even without yielding what one might think is the ultimate result, is invaluable. “When a single’s phone rings and you’re calling with a shidduch, and they haven’t gotten a phone call or a suggestion in so long, who can measure what you’ve done for that person?”

This is especially true in today’s climate where the sheer number of singles is “shocking,” according to Mrs. Elefant. And with technology making it ever easier to contact shadchanim, the pressure on them can be overwhelming. “You want to help and are being pulled in so many different directions. You start to work on one person, and then you get another email, another phone call, etc. When I started, I had a little notebook and ten girls and ten boys, and I worked off that. Now I have dozens and dozens of notebooks. Today, when you’re accessible to so many people, it becomes very difficult to respond to everyone and keep things organized. And if a shadchan doesn’t respond, then a person feels like he’s being ignored, which is terrible.”

In addition to meeting singles in person prior to setting them up, Mrs. Elefant’s advice to aspiring shadchanim is to share information and focus on a realistic number of singles at a time. She also warns not to take things personally when they don’t work out. “Move on; it’s not about you. You have to know that you’re doing this for the other person. It’s not about how many dates you set up or how many shidduchim you make. If you’re in this, you have to be in it because you have a real, sincere desire to help singles. As you said – it’s almost an addiction.”

Feeling validated does alleviate some of the frustration for prospective shadchanim like myself, my daughter and my friend. And knowing that our efforts boost the morale of others boosts our own morale and encourages us not to abandon our matchmaking activities. Even if we repeatedly watch elusive shidduchim escape our grasp.

As for myself, I hope to continue being as enterprising as I can. Until I finally reach the finish line, I will try not to refer to myself as a “failed shadchan.” Rather, I would much prefer to be known as “the not-yet-successful shadchan.