he shidduch crisis is painfully unfolding each day — and individuals with a conscience feel compelled to get involved. But will a well-meaning amateur wreck a shidduch before it’s even begun? What newbie matchmakers should know before attempting to split the sea
Miriam was thrilled. A mother of seven and a skilled graphic artist, she’d just redt a shidduch in which the couple went out twice — and reported having a very nice time. But right after saying how pleasant the date had been, the boy threw Miriam for a loop, informing her that he wanted out.
“I kept repeating, ‘But if you liked her, and you had a good time, what’s bothering you?’ ” recalls Miriam. “I felt I should try to find out — help him work it through.”

After several unpleasant minutes of wrangling, the boy finally disclosed that he wanted a different personality type — but wouldn’t specify which kind. Miriam surrendered. Then she had the unenviable task of conveying to the (shocked!) other side that he didn’t want to continue, without being able to give a concrete reason.

“Painful as it is to hear a no, I think people want some understanding,” she says. “I kept thinking: how would a professional shadchan have sorted this out? And how could I ever set this boy up again?”

Being a shadchan is anything but straightforward — it’s a complex job requiring deft maneuvers. How can inexperienced marriage brokers know what to do? When do they gloss over the truth, and when do they tell it as it is? When do they push, and when do they respect people’s decisions and step out?

Family First spoke to both professional and amateur shadchanim to gather insights — and hear the lessons they’ve learned the hard way.

Matches that Make Sense

The first stop in the path to the chuppah is hatching a workable idea. But in their zeal to jump-start the process, says renowned Lakewood shadchan Rabbi Shloime Lewenstein, well-meaning friends often neglect to ask eligible young men or women directly what they are looking for.

“It’s not just about your gut feelings, or what you see working. If a boy wants a bas talmid chacham, or a girl wants a tall boy, you need to know that and take that into account.”

Doing thorough research and redting on-target matches, Rabbi Lewenstein stresses, will avert the “shadchan-who-cried-wolf syndrome” — the matchmaker parents have learned not to take seriously.

Cross-cultural shidduchim, with their often divergent expectations, can be even trickier. Tova, formerly

of Manchester, England, and now living in Flatbush, remembers the first — and last! — international shidduch she ever redt.

“I once redt a European boy to a girl from Boro Park,” she says. “Both good-looking, great middos, and wealthy. I thought it was perfect.”

Then the complications began. The European parents would only let their son date if they met the parents first. So the father — who was in New York visiting his rebbe — met the parents, inquiring all about their business and bank accounts (but not about their daughter). The New Yorkers emerged from the meeting horrified: “Our accountant knows less about our financial situation than this guy,” they cried.

Tova was mortified. To make things worse, the boy’s parents agreed to the shidduch. Still thrown off by the experience, the girl’s parents began hesitantly looking into him. A week and a half later, the boy got engaged — to a different girl.

“Turns out a European yes means, ‘Yes, we’ll let them date when they are in the same country, but meanwhile he’s free to see other girls,’ ” Tova drily explains. “Worst call I ever had to make.”

Getting It Off the Ground

Once the shadchan has an idea, he prepares the sales pitch, finding just the right words to galvanize the parties involved. The boy’s side is customarily approached first, unless Shadchan has reason to believe the girl’s parents may give a fast “no.”

Shadchan glowingly describes the girl, stressing why the match seems compatible, and offers references.

Once Team Boy does its research and assents, Shadchan does the same for the girl’s side. When both sides are game, Shadchan usually arranges the first date.

Chava Plaut, a young mother who’s set up many couples and made one shidduch, warns that not everything heard should be said — even if it’s true, and even if it came from a parent.

Once, a mother described her son to Chava: “He’s great, just not the tzaddik type.” Mom was trying to convey that her son was not Mr. Eidel, which was fine for the shidduch in question. Wisely, Chava did not pass along this wording — potentially a huge turnoff — and the couple went out.

“Too much detail can kill,” agrees Yoely Weiss, a Monsey grandfather who’s made an impressive number of shidduchim with his wife, Rechy. “What you think is a maileh — that the older brother went to Brisk, or that the grandparents are very balabatish — might be just the thing that puts them off.”

He advises beginners to be upbeat but vague, letting parents draw their own conclusions during the exhaustive checking process.

When it comes to talking money, which Chava terms the “least pleasant part of the process,” shadchanim should be professional and matter-of-fact. If one side expresses shock or dismay (“That’s all they’re offering?!”), she advises matchmakers to stress that (a) figures should not be taken personally — this is what they feel they can manage, and (b) you are happy to pass along specific requests or feelings. By gently nudging each party toward a compromise while stressing the mutual goodwill — the sincere desire to make this work — most shadchanim can avoid a financial impasse.

Ayala, a young but active shadchante, notes that it can be uncomfortable for parents to share financial specifics with a woman half their age. She reassures parents of her complete discretion and confidentiality.

If they still feel uncomfortable, she is prepared to let go and have them transfer to a more professional shadchan.

“The young person can’t be insulted,” Ayala says. “This is about building people’s futures — it’s not about you.”

After the First Date

As shadchanim well know, just getting a boy and girl to go out is a huge achievement. After that first date, what’s a reasonable time frame in which the boy should get back with an answer?

According to Rabbi Lewenstein, there’s no reason it should be later than 10:30 the next morning for the first two dates. (If 12 p.m. comes and goes, Rabbi Lewenstein’s personal approach is not to call unless pressured by the girl’s side. He feels strongly that boys must be trained to take achrayus — get back with an answer without being nudged. Other shadchanim will prod the boy’s mother when no answer is forthcoming.) As the relationship becomes more serious, a few more hours is reasonable. And if someone dated six or seven times and stands on the cusp of a big decision, he or she is entitled to a day or two to let it sit.

“It’s not geshmak for the other side, but it’s fair,” Rabbi Lewenstein says.

When one side has reservations, the big question becomes: to push or not to push? How can the shadchan discern whether there’s potential?

“I’m not a pusher,” admits Rabbi Lewenstein. “If the issue was perception — for example, the girl came across as uninterested to the boy, but tells me she had a great time — then I’d push. But in general, the person has to want. You have to have a reason to go further.”

In this veteran shadchan’s view, many amateurs mistakenly insist on “innocent until proven guilty.” Because they’ve put their kishkes into the match — possibly the first one that ever got this far — they demand unassailable explanations: “You don’t like her? Prove to me why not!”

In contrast, experienced shadchanim are less likely to take it personally. “I have a lot of people going out, and most don’t work,” Rabbi Lewenstein shares. “I’m used to it.”

Sari, a talented Lakewood woman who’s made numerous shidduchim even as she seeks her own intended, says beginner shadchanim must know it’s okay to seek help from more experienced professionals.

“If there’s a bump along the way, if the parents have concerns and you’re not sure what to say, reach out,” she advises.

She remembers a shidduch that seemed doomed. The girl met Sari shortly after the date and began shaking her head. “What were you thinking?” she hissed.

Despite this reaction, Sari felt strongly about the match. Knowing the girl — a family friend — couldn’t hear it from her, she reached out to a professional shadchan, who gently convinced the young woman to try again. Today, the couple has several children, and Sari enjoys frequent Shabbos meals in their home.

Sometimes a dater’s concerns are real and significant. In these cases, Rabbi Lewenstein cautions novices against overstepping boundaries and sharing “definitive” opinions.

“If a girl says, ‘He’s such a baal middos, but I’m not sure I have feelings for him — what should I do?’ that’s when you need to step out,” he says. Shadchanim should direct the questioner to a mentor or rav — not just a talmid chacham, but someone with considerable experience in family and relationship matters.

Being the NaySayer

Most matches will not be a go, heralding the most unsavory task: communicating rejection.

If the date was pareve, almost all shadchanim advise against giving a reason — unless it’s a quality that can be improved, like dress or hygiene. For unchangeable qualities — like facial features or personality — many shadchanim use generic phrases like, “She didn’t see it working;” or, “For now, it looks like it’s not the right one.”

Shadchan Sari prefers to be more specific. “As painful as it is to hear a reason, it’s more painful not to get any feedback,” she asserts, drawing also on personal experience. She’ll offer feedback like, “It seemed your personalities weren’t a good fit,” or, “Hashkafically, she felt you were each headed on different tracks.”

Particularly if the date flowed smoothly and a “no” will stun the other party, Sari feels a more detailed explanation is warranted.

When one side refuses to offer that explanation — she calls it a “shadchan’s nightmare” — Sari tries getting a rebbi or mentor involved. If, ultimately, no substantive reason is offered, she might tell the person, “It would be difficult for me to set you up again if I don’t have a clear picture of what didn’t work.”

Similarly, if a party consistently commits a faux pas, shadchanim would do a disservice by withholding the information. If a girl constantly turns boys off, Sari offers as an example, by grilling them about their learning schedules and how he maximizes his spare time, she needs to be sensitively informed of the problem. Likewise for a boy who arrives habitually late.

Sari says shadchanim have to be extra sensitive with girls, who’ve often waited so long and pinned so many hopes on this date.

Girls who receive an unempathetic “no,” Sari notes, often beat themselves up. “If only I’d gotten my hair done; if only I had the right degree…. it could have worked,” they might think.

“Be warm and supportive. Say something like, ‘You’re going to find someone more compatible, more deserving of you,’ or, ‘You were a pleasure to work with. I’ll continue to look out for a special boy who will appreciate your sterling qualities.’ ”

Sometimes, to avoid coming across as superficial, boys couch their reasons for rejection in more acceptable terminology. “ ‘She’s too frum’ could really mean ‘I don’t like her nose,’ ” Ayala points out.
In these cases, using a friend-cum-shadchan presents an advantage: said boy will more likely be open with his pal than an intimidating 50 year old. But regardless of the shadchan’s age, a truly mentshlich boy will be honest and forthcoming.

“Don’t waste everyone’s time,” Sari implores. “If you are looking for a very attractive, high-maintenance girl, tell the shadchan. She won’t pass it on, but she’ll know for the future. It’s not fair to play with people’s feelings.”

Shloime Lewenstein works hard to avoid surprise rejection by soliciting and giving balanced feedback throughout. If a boy or girl has doubts, he gently conveys them to the other side, while retaining hope for the shidduch.

“You have to play both sides,” he says. “You can’t tell a girl, ‘You’ll probably be dumped next date,’ because then it’s guaranteed to fail, but you can gently prepare her for the possibility. So 95 percent of the time, the no is not a shocker.”

Likewise, Ayala observed that most noes are predictable. “If you’re totally taken by surprise, you might be missing some social cues,” she suggests.

One of the most pleasant parting statements to use, particularly when the couple has dated for a while, is, “I don’t think you’re for me, but I respect you enormously and will be thinking of you for others.”

“I’m touched when I hear that,” shares Meira, a girl who’s dated for eight years. “That’s called parting b’shalom.”

Finally, reminds Renee, a mother of several children in shidduchim: never relay sensitive or delicate information via text. The shadchan should pick up the phone.

Words of Advice

Battle-weary but determined shadchanim are happy to share the mistakes they made — and insights gleaned.

Chava Plaut once worked hours on a shidduch, carefully placating each side time and again. Eventually, the couple got engaged, then married, but no shadchanus was forthcoming. “Different cultures have different assumptions about paying shadchanim,” she says. “If you’re doing this as a parnassah, make your fee clear from the get-go. If not, have zero expectations.”

In general, Chava feels matchmakers must be extraordinarily selfless. “Don’t do it for yourself. It’s effort, it’s time, and you won’t always have anything to show for yourself. The more people feel you’re doing it for them, the smoother the shidduch will go.”

Monsey shadchan Yoely Weiss urges fellow matchmakers to try especially hard for girls, offering generous doses of empathy. He says people should not be afraid to ask a girl, “Would you take someone younger, shorter, or much older than you? A family without much money, or a less-frum family?”

“Girls can answer how they want, but let them make the rules,” he contends. “Don’t make assumptions. You may be surprised by the concessions a girl who really wants to get married will make.”

The old-school father and grandfather also warns shadchanim: it ain’t over till it’s over. Even once the engagement is announced, Shadchan must be prepared to smooth out pre-chuppah bumps.
Once, a chassan gifted his kallah with an heirloom one-karat diamond. Mr. Weiss, the shadchan, soon received a phone call from the outraged mechutanim: “How could they do that? It’s so old, this diamond must be from his grandmother!” It took several conversations over a few days — and lots of patience — to pacify the bride’s side.

“We shadchanim are also responsible for maintenance,” Mr. Weiss jokes.

Shloime Lewenstein says one of the most important lessons he’s learned over the years is that background and upbringing do matter. “I used to think it was irrelevant — I was very liberal,” he admits. “But feedback has taught me it’s not so simple. The way a boy or girl grew up will affect many, many things. I’ve become wary of matching couples from substantially different backgrounds.”
The seasoned Lakewood matchmaker has also become progressively more discreet. “It’s a davar pashut [to be discreet], but people aren’t like that,” Rabbi Lewenstein says. “I’ve grown a lot myself this way.”

Ayala, who dated for several years before finding her bashert, reminds shadchanim that even if nothing materializes, a shidduch redt is enormously appreciated. “So many friends tell me: I really appreciate your call. It means someone is thinking of me.”

Sari wholeheartedly agrees, exhorting shadchanim to “just redt it” — overcome their hesitations and suggest a shidduch even if they’re not certain about the personality fit (since no one can accurately predict that anyway). She also encourages people not to shy away from sensitively suggesting a divorcee they believe would be compatible to a never-married person.
“The girl would rather have the opportunity to turn it down, than not be thought of at all,” she says. “Especially if she’s an older girl.”

But accompanying this eagerness must be super thick skin. Shadchanim are among the most maltreated professionals, on the receiving end of endless gripes, frustrations, and even insults. (“How can you even suggest such a shidduch?”) Despite the heartache, most of these dedicated men and women persist in their holy work.

“No matter how many people get insulted or don’t want to talk to you anymore, when that one shidduch happens, you’re on top of the world,” shares Yoely Weiss. “The feeling is so powerful that you know you’ll keep doing this. All the agmas nefesh becomes worth it.”

Tips for working with beginner shadchanim — from the novices themselves

• Treat us with respect. You might be hurt or frustrated, but don’t address this shadchan differently than you’d speak to a professional. “I once redt a shidduch that was a real mistake,” says Ayala. “The boy said no after only one meeting. The girl’s father was irate — he lashed out at me. I understood his upset — the boy should have given it one more chance — but it was the last time I ever redt his daughter a shidduch. I was too scared.”
• Ask permission. If you feel the need to transfer to a more professional shadchan, that’s legitimate, but discuss it with Junior Shadchan first. Reva, who teams up with her young but astute husband in suggesting shidduchim, relates that she was particularly relentless about a certain shidduch, calling her friend’s parents frequently to remind them. Several weeks later, Reva found out the couple was engaged. The parents had gone to a professional shadchan without even informing Reva, and she felt used.
• Express hakaras hatov. Often, a professional shadchan will redt three or four girls to a boy, but one is reinforced by the independent suggestion of a friend. If that happens and the couple goes out, says Reva, call to thank the friend — she was the impetus.
• Consider the advantages. Remember that a professional shadchan has more experience, but may not care as much — or be as available. Ayala once redt a shidduch that was immediately transferred to a professional. The match did not get far. “She acted more as a go-between than a true facilitator,” Ayala says of the shadchan. “I was frustrated. I felt that had I been involved, I would’ve invested more efforts in smoothing out the edges and making it work. I knew both sides so well.”

Can singles serve as shadchanim?

How one special woman does it — and how to replicate the model

A head counselor of a girls’ camp for years, Sari is a people person who knows hundreds of girls. Her married cousin, a gregarious frequent-hoster in Arzei Habirah, knows hundreds of boys. The two teamed up, and to date, Sari has made ten shidduchim — even as she continues to seek her own intended.

How does a single girl manage the give-and-take?

“I always handed it over to a professional shadchan — or experienced married woman — when it came time to speak directly to the boy,” Sari says, noting she is very close with several shadchanim. “Otherwise it would have been too awkward — the boy technically could have been for me.” But, she adds, synergy with the co-matchmaker is essential.

Sari feels strongly that singles should get more involved in shidduchim: they are a population with more time, networks, and resources. What’s more, many know the boys well — they went out with them! Of her many successful shidduchim, at least two involved boys Sari once dated.

Her wildest match, incidentally, began with a bungled date. “I’m usually pretty on target, but I once set up a girl with a boy who had no shayachus,” she relates. “It was the wrong type completely, but the boy — what a mentsh! — ended up thinking of a friend for this girl, and the two eventually got married. I was so impressed that I set him up with someone else, and they got engaged. It was a double mazel tov!”