The Shadchan Says

January 28, 2021


I am a 23-year-old boy, and I am currently seeing someone. In fact, I am ready to get engaged to her, but she is still not sure. We’ve already been on seven dates. Is there a specific number of dates required before getting engaged?

Mrs. Krupenia answers:

Every social circle has its own average when it comes to the number of dates that is considered appropriate, but it is irrelevant to the greater goal. For example, someone who has a complicated background or a broken engagement may need more time. Therefore, counting dates is counterproductive to what you need to do. The quality of the dates is much more important than the quantity thereof.

When you are dating, you are not seeking to achieve a certain number of dates; you are seeking to acquire the information necessary for moving to the next stage. Focus only on the amount of progress made.

There is always the possibility of having an unpleasant date, even when things are actually going very well. One of you could be tired or not feeling well, or some mishap might occur, and that could lead to a setback. If you are meticulously counting the dates, you will find these mishaps unnecessarily stressful. You’ll say, “I shouldn’t be at this stage when I’m already at the third date!” But the stage doesn’t always correlate with the number. You may be on your third date, but if you need another first or second date, have another first or second.

It is imperative to use the dates to gather information that is appropriate for that stage in the relationship. At first you will look to see if he or she is a growing person, if the two of you are basically on the same hashkafic wavelength, if he or she has good middos—if you are seeing the basic qualities that would pull you to continue. Base your decision not solely on the fact that nothing is wrong, but on the fact that something is right. Something that drew you to the conclusion that you are curious enough to get to know this person better. There has to have been progress. Does the person have the qualities you think she would need to make a good spouse? A good parent? You have to know that you have all the relevant information.

Seek out a person with whom to speak things over, perhaps a rosh yeshivah, a rebbi, or a dating coach; someone objective. Your parents are wonderful, but they are very emotionally invested in you and therefore may not be sufficiently removed from the situation to appropriately advise you. I coach many boys and girls, but I don’t coach my own children.

Your coach or mentor will help you see if there is progress. If there is progress, you can continue. If after seven or eight dates, everything has plateaued, then perhaps you should rethink it. Going out on many dates has its own risks. How many times can you explore the same topics before they start to seem banal? You may reach a point at which the relationship stagnates, and it becomes difficult to find places to go and things to talk about. That is when you start to focus too much on the other person’s flaws, and they appear to magnify. The conversations may feel strained, not because it isn’t a good shidduch, but because you took too long to make a decision. The benefit of going on yet another date has to outweigh the risks. Continuing at a certain point—when there is nothing to gain and you already have all the information—does not accomplish anything, and the benefits no longer outweigh the risks.

The shadchan should make sure to know what is going on with both sides to ensure that both are on the same page. If only one of the parties needs more time, they should provide a reason why. If you are still unsure, instead of telling the shadchan, “I need more time,” say, “I need more time to find out more about this specific thing,” or, “I need more time to get more comfortable with…” First, this ascertains that there is in fact a purpose in the delay, and furthermore, the clarity makes it easier for the other side who may already be ready. Then, offer to plan the date. Because the other side doesn’t know what you want, need, or expect anymore.

But truth be told, whenever I have a case in which only one side needs more time, the other side always appreciates it in the end.

Suppose after these seven dates, the girl decides not to continue. That would be very painful. But one cannot begrudge her the amount of time she needed to come to that conclusion, even if it seems excessive. She has clearly seen your many wonderful qualities, which are what pushed her to pursue the shidduch for this long. She was trying to make it work. She probably had daas Torah encouraging her to give it another try.

The number of dates is irrelevant. Seek advice to make sure there is sufficient progression in the shidduch, and may Hashem grant you both clarity.


Sometimes an incident may seem insignificant to the boy or girl, but to me as a shadchan and dating coach, it is revelatory.

A girl called me after a date. She was impressed by the young man’s thoughtfulness.

“He lent me his phone on the way home,” she said. “He told me to call my parents to tell them we would be later than expected. It was such a thoughtful and responsible thing to do, wasn’t it?”

I concurred. “Why were you running later than expected?” I asked. “Did you lose track of time?”

“No, we left on schedule,” she replied. “But he accidentally took the Garden State Parkway North instead of South.”

I blinked. “Why didn’t he just exit, then? And turn around?”

“He couldn’t,” she sounded casual. “He’d gone onto the express lane. So there were no exits for a while. He realized we’d be late, so he told me to call my parents. I was impressed with that.”

When I put the phone down, I shook my head. “This has all the markings of a positive outcome,” I thought. “If he made a mistake like that, and all she noticed was his thoughtful and responsible reaction…this shidduch is going places.”

Indeed it was.

And the chassan did not get lost on the way to the wedding.

Tip for parents

If a boy is coming from a different city to meet your daughter, don’t expect him to plan the dates. He may try to find a venue from the circulating lists of dating sites, but he won’t know the actual lay of the land. His GPS will tell him something is 10 minutes away, but you’d know that traffic brings travel time up to a half hour. Or he may innocently take her to the zoo that your family has visited every Chol Hamoed for the past 19 years.

If you’d invite an out-of-town friend or relative over, wouldn’t you plan the itinerary? Please do the same for dates, even if you have a daughter.

Dating suggestion

Be advised that COVID-19 is affecting available places for dating. Most privately owned indoor venues require prior reservations. And most importantly, be flexible. Everyone is out of their depth now. During these times, I feel strongly that the boy and girl alternate planning the date.

Mrs. Krupenia made her first shidduch over 20 years ago. She is a shadchan and highly effective dating coach, guiding both boys and girls from phase to phase on their shidduch journeys. She can be reached at

The Shadchan Says is a biweekly column which will feature interviews with well-known shadchanim in Lakewood. Readers are welcome to submit questions for the shadchanim at