Inside the Shidduch Process: Matchmakers Reveal the Truth

Shidduchim. A single word that carries with it enormous hope, excitement, pressure, disappointment, prayers, and sometimes deep frustration. Anyone who has gone through the matchmaking world can usually tell a story about the long road that eventually led them to their zivug.

For some people, the journey is surprisingly quick and smooth. For others, it becomes a winding and emotionally exhausting process that seems endless, with no clear sign of where the road is actually leading.

And standing in the middle of this complicated world are the matchmakers.

The people holding notebooks, spreadsheets, WhatsApp lists, family details, résumés, and endless names. The people who quietly spend their days trying to build Jewish homes.

But what really happens behind the scenes of the shidduch world? What drives matchmakers to suggest certain matches and not others? What frustrates them? And how can singles and parents work with them more effectively?

To better understand the reality, we spoke with three experienced matchmakers:

• Esti Lehab, who mainly works with Chassidic and Lithuanian first shidduchim
• Sarah Lipshitz, who specializes in Lithuanian circles and baalei teshuvah
• Yaakov Paz, who primarily works within the Chabad community

Together, they offered a fascinating look into one of the most emotionally sensitive worlds in Jewish life.

“Don’t Be Afraid to Contact Matchmakers”

How do matchmakers even hear about potential singles?

“In the beginning, I used to actively approach people,” Esti explains. “Today, most people come to me themselves.”

She also relies heavily on matchmaking networks and word of mouth.

“One thing I really appreciate,” she says, “is proactive parents. Parents who don’t wait passively, but as soon as their son or daughter reaches shidduch age, they start reaching out.”

Yaakov agrees that the system today looks very different from previous generations.

“It’s no longer like the old days where matchmakers walked door to door,” he says. “Today, once your name becomes known, parents start contacting you constantly.”

Usually, he requests a concise profile including:

• Family background
• Parents’ occupations
• Educational background
• Community affiliation
• Goals and aspirations

Based on that information, he begins trying to identify possible matches.

The “Matchmaking Sense”

Some people strongly prefer receiving suggestions only through relatives or close friends rather than professional matchmakers.

The matchmakers understand the logic behind that.

“Of course someone close may know you better personally,” Esti says. “But they also know far fewer people.”

And according to her, experienced matchmakers often develop something difficult to define precisely:

“A matchmaking sense.”

“It may sound strange,” she admits, “but many experienced matchmakers can often sense compatibility after just one conversation with the parents.”

That does not mean they always succeed, but over time they begin recognizing certain patterns, personalities, expectations, and emotional dynamics.

Sarah shares a striking example.

At one wedding, she heard about a widowed woman looking for a second marriage. At the same time, she was helping an older single man searching for a match.

“The next day they met,” she recalls. “Three weeks later they were engaged.”

The Emotional Weight Matchmakers Carry

All three matchmakers emphasized that the work is emotionally far more difficult than most people realize.

“People think matchmaking is glamorous,” Yaakov says. “But statistically, most suggestions fail.”

According to him, matchmakers constantly deal with hopeful, vulnerable people already emotionally exhausted by disappointment and waiting.

“We are handling people’s lives,” he says carefully. “You have to be extremely sensitive not to hurt anyone.”

Sarah explains that despite handling hundreds of suggestions annually, only a small number actually end in marriage.

“There can be months without a single engagement,” she says.

Because of that, most matchmakers cannot realistically rely on matchmaking alone as full time income.

Should Parents Pay Matchmakers More?

One of the most surprising parts of the conversation involved money.

Yaakov openly argued that parents who truly want greater attention from matchmakers should consider offering payment even before an engagement happens.

He claims that when matchmakers know their time and effort will be appreciated even if a match does not succeed, they often invest more energy into pursuing suggestions and facilitating meetings.

“If someone offers compensation for every serious suggestion,” he says, “that name naturally rises higher in the matchmaker’s mind.”

Still, not everyone agreed.

Esti admitted that after years in the field, financial incentives matter less to her emotionally than the satisfaction of successfully helping build a Jewish home.

“When you finally help create a shidduch,” she says, “the feeling itself is so enormous that money becomes secondary.”

Sarah acknowledged that financial incentives can absolutely motivate additional effort, but insisted she could never intentionally neglect one person simply because another family paid more.

“Please Just Respond”

One issue that repeatedly frustrates matchmakers is silence.

“When I suggest a match and people disappear completely without answering,” Esti admits, “it makes me far less motivated to continue helping them.”

Even a polite rejection matters.

“Just explain respectfully why it doesn’t fit,” she says. “That basic courtesy goes a very long way.”

Sarah adds that she often invests even more effort into singles who are struggling emotionally or receiving fewer suggestions.

“I see that as my real mission,” she says.

The Problem With Pictures

Yaakov believes modern technology has significantly complicated the shidduch world.

“In the past, many successful matches happened because people met before seeing pictures,” he explains.

Today, photos are often exchanged immediately through WhatsApp before any serious inquiries even begin.

According to him, many potentially excellent matches now end prematurely based entirely on superficial first impressions.

Why Flexibility Matters So Much

One theme all three matchmakers returned to repeatedly was flexibility.

Esti described emotionally healthy families as those willing to hear suggestions outside their original “perfect image.”

She recalled parents who were open minded about things like age differences, appearance, or background, and who ultimately built extremely happy homes.

Sarah strongly warned against becoming trapped in rigid “shopping lists.”

“I know families who insisted on extremely specific backgrounds,” she says, “and eventually found happiness דווקא somewhere they originally never would have considered.”

The Challenges Facing Baalei Teshuvah

The matchmakers also discussed the unique challenges many baalei teshuvah face in the shidduch world.

Sarah explained that difficulties often arise less from the person themselves and more from differing mentalities, family cultures, or expectations between communities.

Still, both Sarah and Esti emphasized that attitudes toward baalei teshuvah have improved significantly in recent years, especially within certain communities.

“Keep Trying”

At the end of the conversation, all three matchmakers shared similar advice.

Be proactive.
Be polite.
Be flexible.
Keep trying.
And never stop davening.

“Persistence matters enormously,” Esti says.

Sometimes, she explains, the singles most willing to hear suggestions, ask for help, and continue trying despite disappointment are ultimately the ones who succeed.

And perhaps most importantly, the matchmakers emphasized remembering that behind every résumé, every inquiry, every phone call, and every “yes” or “no” stands a real human being carrying enormous hope for the future.