Articles

Match Point

December 4, 2025

Insight and Strategies to Help Navigate the Shidduch Maze

 

By Mrs. Etty Gartenhaus

Facilitated By Shoshana Gross

 

Q: I’m 21 and in the middle of dating someone. I had four very good dates with this boy, and I felt like things were going somewhere. But on the fifth date, things just didn’t click, and I feel discouraged. Does that mean I should end the shidduch? What should I do next?

 

A: Dating today is very different from the way it was years ago. Many years ago, fathers could arrange matches as soon as their children were born! I once heard a story about two friends whose wives were having babies. They decided that if one had a boy and the other a girl, they would marry them off to each other. And they did. But even then, it was just as much min haShamayim as it is today.

Today, we have dating, and it’s the system we use. But we need to remember that dating is an artificial setting. You can tell, to a certain extent, if a boy is a mensch, if he has good middos, maturity, and a compatible personality. But it’s not perfect. People are nervous, they don’t reveal their true selves, and sometimes they portray themselves differently than they are.

I happen to know a 19-year-old girl who was very shy and hardly talked during dating. But she was known to be a wonderful girl, both inside and out, and he married her. Baruch Hashem, they’re extremely happy and have a beautiful family. Many times, even quiet or reserved people are more outgoing than they appear on dates.

I also know a girl who went out with a boy around seven times. The last date wasn’t good, so she ended the shidduch. Months later, she was in a car with coworkers and heard them talk about how they had initially broken off with the boys who eventually became their husbands. Her mother asked a shadchan for advice. The shadchan told them to reach out to the boy and see if he was still interested. He was, and the second time around, they became engaged.

It’s important to understand that not every date will be perfect. Some dates can be really nice and others not so much. That’s normal. Real life isn’t like sitting at a table for hours, just talking. Married couples with families don’t often spend that much uninterrupted time in conversation. Life is busy with kollel, business, work, children, appointments, and more! Even the most intellectual girl, once married and a mother, will become more focused on whether the baby burped and making supper.

Dating is an imperfect system. You can’t see the full picture of a person in a few hours. But you can observe how they treat others and how they behave. Because a person’s character is revealed through actions, not just conversation.

I read a story about an almost-engaged couple who went out to eat, and the waiter took a long time bringing their food. The man yelled at the waiter, and the girl was mortified. She did not marry him. Contrast that with another couple I know who were once in the same situation. They used the time to schmooze and connect, and they had a great time. They are now happily married with many children.

Your job is to try to be yourself on a date as much as possible. Don’t give up a good shidduch because one date isn’t exciting. Look for consistency, middos, and respect, and trust that Hashem is guiding the process.

 

Shidduch Story

A wealthy man had a daughter to marry off. He spread the word that anyone who redt a shidduch would receive a ruble.

There was a very poor man in the same town, and one day he was desperately hungry. He remembered the offer and thought, Maybe I can suggest someone and earn a ruble? He thought of a random name and knocked on the wealthy man’s door. “I have a shidduch idea,” he said. Then he gave the name and asked, “Can I have my ruble?”

It was obvious he had come just for the ruble, but the wealthy man believed in hashgachah pratis, and thought, If this person came to me in this way, it’s from Shamayim. So he looked into it. And it was a perfect match.

You never know where a shidduch will come from. Sometimes, the most unexpected suggestion turns out to be the one Hashem sent.

I once heard a personal version of this story. When the young lady got engaged, she shared that her father, a serious ben Torah, constantly asked people for ideas, but nothing worked.

Then her younger brother, a ninth grader learning out of town, met a bachur and thought of redting the idea. The boy was Sephardi, and this girl was a classic yeshivish type. But they went ahead with the idea, and baruch Hashem, they’re happily married.

And it all came from the most unexpected source.

 

Dater’s data 

Don’t say anything negative about yourself on a date. And this isn’t only for dating—it’s smart for everybody to avoid talking negatively about themselves.

I remember a friend once telling me she wasn’t happy with a specific facial feature. I had never noticed the issue, even though I know her very well. But once she pointed it out, it became something I noted.

It’s the same with personality traits. If you tell the person you’re dating, “I’m opinionated,” he may remember that and hold it against you later. Normally, he probably wouldn’t even have noticed. Why put yourself down? Why point it out?

Sometimes people even say, “I never passed a math test in school” or something they feel is an innocent remark. It’s not necessary. If it’s not something that needs to be said, then don’t say it.

Bottom line? Don’t talk badly about yourself: not to a date, not to a chosson, not to a spouse, not to anyone.

 

Parents in the parshah 

Mothers, observe your daughter when she comes home after a date. Many mothers can determine how their daughter’s experience went just by looking at her face—especially if she comes home glowing, excited, and really enthusiastic! Some girls are more reserved by nature, and that has to be taken into account, but a mother will often be able to tell if her daughter was happy and if the date went well.

This is important, because sometimes a girl comes home excited, only to wake up the next day feeling nervous. This is completely normal. Girls might be happy one day but insecure the next, especially if it’s their first or second boy. On the other hand, if they’ve gone out many times before (especially if they had negative experiences), they might worry about whether things will work out.

Either way, intuition plus davening is crucial. I always daven for my grandchildren, and I did the same for my children. I ask Hashem that if this shidduch is the right one, it should go smoothly. And if it’s not the right one, the process should go smoothly too.

It’s a mother’s observation, combined with tefillah and trust in Hashem, that are the ingredients of a successful experience.

 

Mrs Etty Gartenhaus has been a kallah teacher for close to 40 years and gave classes to women for close to 18 years. She is also a longtime teacher at Bais Kaila and is involved in giving advice for shidduchim and coaching young women.