By Baila Sebrow


I have a daughter who got married later in life after enduring much agmas nefesh as an older single. I promised Hashem that as soon as she got married I would take on the mitzvah of helping older single girls find their shidduch, the way Hashem helped my daughter find a shidduch. So I guess you can call me a shadchan who wants to help alleviate the shidduch crisis.

I am very happy to do the mitzvah. I don’t ask for any money, and I spend every night on the phone, sometimes even till a few minutes before Shabbos. I do not want to speak lashon ha’ra, but I am so frustrated by some of the singles. They don’t treat dating the way my daughter did. Just last week I set up an older girl with a guy and she said no to him because he didn’t take her to a restaurant for the date. I think that it’s chutzpah for a girl of any age to expect the boy to wine and dine her. And she is not the only one. Also, some of the girls have bad attitudes, and I wonder if they really even want to get married. 

I know I am new at this, and I really do want to continue helping singles, but I feel like they don’t appreciate me when they are not nice to me, and they are not even so nice to the men who take them out on dates either. Do you have any suggestions?


Since you are new to this, I need to point out something that you may not realize creates distress amongst single women. In today’s world there are women who get offended if you refer to them as “girls.” To those who take serious offense, it is almost as bad as committing a capital crime. Years ago, nobody minded being called a girl, and in those days even older ladies referred to themselves and their friends as girls. But since we are living in a “cancel culture” anyway, this is just another area that some people become emotionally and verbally militant about.

That said, it’s possible that the people who are exhibiting a bad attitude towards you might be doing so because they feel you are offending them. The lesson to be learned from this is that in this day and age, females (I hope I can still even use that part of speech!) insist on being called women.

What you are doing for the singles community is to be admired. You are a role model for many whose children experienced challenges in dating and finally got married. You are paying it forward in the most selfless way possible. You should be encouraged, applauded, and congratulated for your endeavors to do chesed without expecting remuneration in return. Instead, you are met with unappreciative attitudes. You need to realize that those who mistreat you will mistreat others, too. Abusive people abuse when they can and because they can, and oftentimes the victim will be the very person who tries to help them. There’s a reason why the expression “biting the hand that feeds you” is used often.

The good news is that most singles are very grateful and show tremendous hakaras ha’tov to those who assist them. You are under no obligation to help anyone who treats you badly. Moreover, to be ethically correct, there is no way you can vouch for somebody who is not nice to you, and, therefore, matching them with a kind person will place you in the position of being dishonest. There is nothing wrong with telling somebody that you cannot help her anymore, wishing her well, and moving on to those who are deserving of your efforts.

You broached a topic that men in the dating arena complain about all the time. You are correct that there are women of all ages who insist on being wined and dined on a date, or else they will claim that the guy is cheap. That is so very wrong on so many levels. No man should ever feel obligated to spend a lot of money on any young lady he barely knows. I have said this in the past, and I will say it again. A date, especially in the very early stages of a potential relationship, is nothing more than a glorified interview. Women who want to be treated to upscale dining need to look at it from the perspective of applying for a job. Would they expect to be wined and dined when they are applying for a job? Would they turn down a job offer because the interviewer didn’t take them out for a steak dinner?

There are women who erroneously believe that a good date is one where the guy planned a beautiful outing and spent plenty of money on them. Even the men who can afford to lavish their dates with luxurious outings are not happy about it if they feel pressured into doing it. Nobody wants to be taken advantage of, regardless of the amount of money in one’s bank account. It is quite the turn-off for a man when he is realizes that he is being ill-used.

I don’t know who initiated that dating must be an expenditure for the man. I cannot imagine that men who have been dating for a long time don’t get tired of being an ATM, even if they continue doing so because that is what is expected of them. As a shadchan, I can tell you that I have had many cases where a relationship was going well until the man chose an outing that did not involve a restaurant, even if it was initially mutually decided on, and on the date, he offered the lady something to drink. Yes, there are women who will drop good men for this reason.

That brings me to the other issue you raised. You questioned whether the women with whom you did not have good experiences really want to get married. That is an interesting question, and the answer might come as a shock. No, not everyone wants to get married. It is assumed, especially in the frum world, that every man or woman who is single is a victim of the shidduch crisis. For the record, the term “shidduch crisis” is oftentimes misused, and it absolutely does not apply to every case. It was originally coined amongst very young daters, because young ladies typically start dating right out seminary, and the young men their age do not date until later. Therefore, there are fewer men available to such young ladies, and for those who were left behind because they couldn’t find a shidduch, they were considered victims of the shidduch crisis.

As young ladies get into their twenties, no such crisis exists. There are plenty of young men in their age range available to them for dating. But as you know from your own experience with your daughter, it takes more than two human beings with beating pulses to call it a mazal tov. There is always the issue of compatibility, attraction, and the reality of what people wants as opposed to what they have to offer for the type of shidduch they want. In many cases, when singles do not find what they are looking for they become frustrated. Some give up altogether and decide that since they have made a successful life for themselves, they don’t need a man. Such women actually become angry at a shadchan who dares to suggest a shidduch that they had either previously rejected or whom they consider beneath their dignity to date. Rather than thank the shadchan for his or her time, there are those who act in ways that are just not nice. Then there are singles who, for whatever reason, never wanted to get married in the first place and consider it an intrusion when a shadchan suggests a shidduch to them.

Working with singles who are not young has to be handled gingerly. You are dealing with people who might be in pain. Many have experienced heartbreak, and regardless of how successful and accomplished they may be, if they are lacking something in their life that they want badly, it will be reflected in their attitude. You need to adopt an image of advocacy. You should never compromise on expecting courtesy and respect, but singles need to feel that you are on their team.

Frequently, parents of older single women and men will call a shadchan and ask him or her to find a shidduch for their daughter or son. The biggest mistake shadchanim make in such a circumstance is going ahead and trying to help without interviewing the single person, and, with all good intentions, base their search on what the parent says. As people get older, their needs and tastes change, so while the parent describes a particular type that the daughter or son needs and wants, the parent is completely off base and not on board with what their child actually needs and wants. And when the shadchan suggests a shidduch based on misinformation, the shadchan is seen as the antagonist!

Never do a search for any single man or woman based on a phone call with a parent or relative, because as hard as you will work to help, you will not only fail but will sometimes be viewed as an enemy. When you receive a call for help, always insist on communicating with the single woman or man. Politely tell the parent or relative that you only talk to the person seeking a shidduch. Not only that, but never be the one to put in that first phone call or you will be considered an intruder.

Insist that the one seeking a shidduch call you until you have established an ongoing relationship. When you do communicate, respect what they say about their wishes regarding the type of person they really want to date and marry. Even if you don’t agree with them, keep silent. It is not your place to judge what you feel they can get or deserve. You do, however, have every right to say that at the moment you may not know anyone for them, but you will keep searching on their behalf. Make no promises that you genuinely believe you cannot keep.

The most important pointer I will give you is to continue giving singles hope. Hope not only makes their situation tolerable, but mentally visualizing that their situation will improve oftentimes becomes a self-fulfilling prophecy. Hope opens the door and gives people the confidence to continue striving for the outcome they have been pursuing and for their personal miracle to be achieved.

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. She can be reached at Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


  1. Suggestion. Don’t be shy about letting people know when their expectations or behavior is off-base. There’s plenty of that going around.


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