WILL YOU RECOGNIZE YOUR BASHERT? Dating among older singles.

Rabbi Shlomo Cohen


In Frum circles there is a pressure to marry off children fairly young (by secular standards). In most cases it is surprisingly easy to match up a couple. Part of the reason is that these children have been raised in a social milieu where this is expected, their friends are all doing the same thing and their parents, whom they’ve been taught to respect, advocate this behavior. So they go off to play house. There are no problems, life is fun, the world is at their feet. They have few expectations, fewer pre-conceived notions and only a rudimentary idea of what they are looking for. It is relatively simple for them to envision a life together since they are both near-sighted, in the sense that youngsters can’t really appreciate getting older, and what they do see is colored by a very heavily tinted pair of rose colored glasses. The process is primarily an extension of what they have been taught in school, at home and what they observe.

Not so the older single. By the late twenties or early thirties the process has become less a matter of peer, community or parental pressure, less hormonal and more intellectual. By the late thirties, early forties it has become primarily intellectual. Thereafter, marriage makes less and less sense. Statistics in the general population show that once a man reaches the age of 40 as a single there is over a 90% chance he will never marry.

For the older singles who read this, please keep in mind that I am speaking in general. You may recognize yourself in these words, you may not. What I say in part or whole may or may not apply to you and you may not even agree with what I have to say. In any event there is no intent to cause hurt. I apologize in advance if your sensibilities are trampled.

Shadchanim, take note! Every mistake in judgement that you make has a price in human sensibilities. Far too many people try to be Shadchanim, after all what could be nicer? Almost as many ultimately do as much damage as good. Be careful. Ask She’ilos.  What you say, the manner in which you set up a match, how you follow through all have ramifications in other peoples’ lives. Few older singles have had only positive experiences dealing with Shadchanim. Most have very real complaints. One off-the-cuff remark may wreak havoc. A young woman I know was already a Kalla. She often came to us for Shabbosim and Yomim Tovim. Several weeks before the Chasuna she went to someone else’s home for Shabbos. I hadn’t finished making Havadala that Shabbos when a car came roaring into our driveway and screeched to a stop. In ran this young Kalla nearly hysterical. “I’m not!… I won’t!…I can’t!… It’s over!… Finished!…..Forget it!”.  It took me almost 20 minutes to calm her down sufficiently to find out what was going on. The woman she was by for Shabbos was Chassidish and mentioned that the Kalla would need to shave her head!!!! Well, as you can imagine this was somewhat upsetting news to find out only weeks before the Chasuna. I called her Chasan long distance and asked him to answer one question, I’d explain later, “Do you expect your Kalla to shave her head?”. I thrust the receiver to the Kalla’s ear in time for her to hear her Chasan say “No way.” Close call. One comment. Be careful!

The forces that come in to play are fascinating and worth understanding. Older singles tend to view themselves as finished products. “I am who I am and I’m not about to change.” The single often has a responsible position and a comfortable lifestyle of some years duration.  They seek a finished product. Thus, every date is a disappointment since it will always be possible to see a few rough edges (unfinished), or find areas of disagreement (not finished to my liking). Few seem to understand that the finishing process is marriage itself and that two people must live together for some time to polish each other and that the process never really ends. It is difficult for the single to recognize that what they seek probably does not exist.

The field is finite. While it might be difficult to face, it is nonetheless true that, at any given time the field is made up of those who have not married for one reason or another.  The ‘cream’ of the crop has been taken. This is not to intimate that you, dear reader, are any less worthy than those who are already married. It does carry a strong message, however. Nobody wants to ‘settle’ yet, to some extent, in all likelihood, if you do not become more realistic you are only hurting yourself. Realism includes understanding that dreams aren’t real, that people are not perfect, that marriage has ups and downs, that compatibility depends largely on your own attitude. “I just don’t see it working” is a pretty poor way to get out of any relationship before it has a chance of developing. The stakes are too high for less than “We’ve got to make this work!”

Status quo is a very strong attraction. So too is inertia. Both speak loudly to the single. “Things are really okay the way they are. Why change?” “I’m comfortable with my life. I have sufficient money. I’m answerable to no one. My space, time and money are my own.”  Virtually all older singles express a desire to marry yet find it extremely difficult to reach a decision. One older single came to me for help. I asked him how many women he had dated over the past ten years. He told me he had dated over 100 different women. I asked “Of those, how many do you feel, in retrospect, were actually good candidates whom you could have married?” His answer, “Not one!” My response – “Seek professional help. The problem is not the women you’ve dated.”

It is very possible for you to miss your Bashert. There is a cute joke that exemplifies this situation. There was a tremendous flood inundating a populated area. Amongst those working to save the lives of the inhabitants was the local rabbi. He was a very sincere individual who placed all his faith in his Creator. As the flood raged he worked day and night to find those stranded in the rising waters and lead them to safety. Finally, as the last people were saved the coastguardsmen told the rabbi to get in the boat. He said he would place his faith in G-d to save him. The waters rose higher and the coast guard sent a special boat to save this hero. Again he refused to get in the boat. The waters rose higher yet until the rabbi was forced onto the roof of the building. The Air Force sent a helicopter, which dangled a rope ladder down. “Rabbi, this is your last chance” they yelled down to him. “I have faith,” he yelled back. At long last the waters swept him away. The Rabbi comes to Heaven and confronts G-d. “I placed my faith in You and yet You let me drown?” And G-d sadly answered “Do not blame me, my child. I sent a rowboat, then a motor boat and finally a helicopter to save you. You turned down Divine Providence and your situation is of your own making.” The moral of the story is quite obvious. Don’t spurn the Shidduchim that are sent your way.

Keep in mind that the Shadchanim, as well meaning as they are, are playing basically a numbers game. If they set up enough dates, some are bound to click. Unfortunately, the matchmakers really don’t know both parties really well and often don’t know either party particularly well. Each Shadchan also has a set of preconceptions coloring his or her view of whom is right, or wrong, for whom. Let’s face it, they’re guessing.  This means that those dates you are sent on are blind in more ways than one. Realizing this should help you understand why dating is so very frustrating and why it requires meeting so many people in order to find The One. But that is all it takes, JUST ONE. Keep telling yourself this. It only takes one!

Most likely, your current dating strategies haven’t changed much over the years. It’s past time to rethink these strategies.

Any business consultant will tell you that you need both a mission statement and a goal to be successful. If your mission statement is, “Perhaps I’d like to possibly marry one of these days, maybe” it’s time for a change. How about, “I’m going to get married!!!” And try a goal like “by this time next year”. Just because you say it won’t make come true, but, like any goal , it is certainly worthwhile and potentially achievable.

Commitment becomes a major issue. All too often singles will date, develop a relationship and when the situation begins to get serious one or the other will find some point which enables them to back out. The only effective antidote to ‘cold feet’ is two pair of socks.  Commitment is scary. The decision to get married is not an easy one. What the singles don’t recognize is that the issue over which they break up is simply real life. Any married couple deals with the selfsame issues on an ongoing basis. Husband and wife cannot, will not and probably should not be in 100% agreement 100% of the time on 100% of the issues. All too often a wonderful Shidach is broken over something that wouldn’t even faze the same couple were they to marry. Don’t get me wrong. Many people are simply not right for one another. In many cases there are dates who have very real, very serious problems.

One factor that is very frightening is the escalating divorce rate. When I was in Jr.high school in the 1960’s there was one girl (this was public school) who came to school in curlers which was not allowed at that time (there was a real dress code). She was sent home, of course, but the reason she did it to begin with was because she was going to her mother’s wedding that night. Her mother was divorced? What a scandal. Mind you she wasn’t even Jewish. Even amongst gentiles divorce was almost unheard of. When I began teaching in the early ‘70’s, again in public school, there was generally one or two divorces in every class. When I became a Yeshiva principal in the early ‘80’s there was perhaps one or two students, out of hundreds, from divorced homes. Now the number is one or two in every class. This issue most likely scares many singles. We can just hear the singles asking themselves, “ How can I be sure that I won’t end up a statistic? How do I know this marriage will work?” In a word- you can’t know. You can minimize the chances of divorce by working hard at pleasing your spouse.

“We’re just not compatible.” How often have you heard (or said) that line. The concept of compatibility is far too subjective to easily define. When I’ve asked singles to be more specific they usually respond with some notion of  ‘being hard to talk to’ or ‘we have little in common’. Compatibility is clearly important. What you are about to read may strike you as strange. Don’t scoff too fast. Conversation on dates tends to be rather heavy. Real philosophical issues are the order of the day. On a number of occasions singles have asked me how it will be possible to maintain that level of conversation over years of marriage. I ask them what they remember of their own parents’ conversations.  For the most part it is all the stuff of daily life. Who will pick up the milk and bread, car-pools, take in the car, fix the plumbing etc. yada-yada and so forth. That is the reality 99% of the time. Ba’alei Tshuva seem to feel that anything their parents did is not correct. Don’t throw out the baby with the bath water. If you come from a good home, the model provided by your parents will actually be pretty solid and, more to the point, it’s the only one you’ll ever have to work with. Try to recall their conversations. Not heavy philosophy. Realize that even Roshei Yeshiva are not having deep discussions with their spouses. Don’t err in thinking that if you don’t find your date an interesting conversationalist that it is over, there is literally nothing to talk about (pun intended). Ask any married couple and you will find that this is true. Compatibility is really a question of common goals and general agreement on how to achieve them. Two people need not share every interest. Their taste need not be the same on most things. Some issues are real. She is a life long vegan; he loves rare steaks for breakfast. Probably not a good match. The area of disagreement is simply too fundamental. While all of us have heard of separate bedrooms, separate kitchens are a bit much.

Having little in common is more difficult to address. Perhaps this story will help. A young man I knew was heavily into skiing. He lived for the slopes. Any woman he would marry just had to share this passion for skiing.  Years passed in a fruitless search for a woman who was Frum, a Ba’alas Middos, intelligent, good looking and a ski freak. Lo and behold, he found her at last – now that’s compatible. Several years later our paths crossed and I asked him how the skiing was, assuming that they were on the slopes every chance they had. Imagine, they were too busy with so many other things that they had only been skiing two or three times (he wasn’t even sure) since they got married. Marriage changes things. That which is of absolute importance now may fade away very quickly later. Remember the friend you had who sat with his or her guitar every night strumming for hours. If they’re married now I’ll bet the guitar is covered with dust. A certain degree of commonality is necessary. Most of what couples have in common develops as the relationship matures. As long as there is a base to build on, don’t be afraid to take the plunge. Trying to find a perfect match is a fruitless search. In point of fact, it will be the differences between you that make life interesting. Beyond certain basic life goals and a few interests commonality is relatively unimportant.

Perhaps the single largest block is the “SHOPPING LIST”. Some people have long and detailed lists of what they want, others deny having a list at all. After dating for any length of time, it is not possible to avoid developing a fairly definitive set of criteria. Certain criteria are crucial and should be heeded. Some criteria should be negotiable. Many criteria are false. Be aware of the difference between a  “shopping list” and a “checklist”. The former sets ironclad parameters; the latter is an evaluatory technique. The former prevents you from considering some very fine potentials, the latter enables you to measure, compare and decide on the basis of merit.

Heading the checklist as necessary criteria are:

Honesty – no relationship can be built without it. This does not mean total disclosure. Later on we will discuss what information needs to be given and at what point.

A compatible level of Frumkeit . He wants her to cover her hair, she doesn’t want to.

Agreement in certain life goals – he wants to live in Israel, she doesn’t. She wants a learner, he’s not one. These are real blockers.

Sensitivity– Is she on a pedestal or seen as maid, short-order cook and laundress? Does he feel respected and treated well or as someone to nag or fight with? A person’s level of sensitivity tends to show up very early in dating, often on the first phone call or date. One widow, looking to remarry, expressed to me her disappointment in the lack of sensitivity men showed her. I asked her to give me an example of what she meant by sensitivity. She told that her first husband, on their first date, made up to meet her at a particular location. He gave her directions how to get there and, at the same time, gave her directions on how to get home. She thought that was very sensitive of him. I asked her if she gave directions on how to get home to her dates when they called to find out how to pick her up. She said no. She was obviously, then, not being sensitive according to her own definition. Her reply was that she had to be careful not to open herself up too quickly for fear of being hurt. That fear is real. It is also totally unfair to yourself or your date. Dating becomes comparable to two empty masks sitting across a postage stamp sized table, sipping coke and …..and nothing!!! You cannot get to know another person without dropping your armor. True, the potential for hurt exists. The alternative is to remain forever dating and perpetually single.

Negotiables on the checklist:

Some religious issues should be negotiable – she wants to keep Chalav Yisroel, he doesn’t. She wants to go to the movies occasionally, he is appalled.  He wants a TV in the house, she won’t hear of it.

Where will we live – she won’t leave BoroPark, he can’t stand it. He wants out of town, she’s concerned about Chinuch for her, as yet, non-existent children.

Parnasa (livelihood) – she wants a doctor, he’s a teacher. He expects her to work; she wants to stay home with (the still non-existent) children. People probably have more expectations in this area than any other. Be realistic.

False criteria:

Most physical criteria – The Gemora clearly indicates that a man should not marry a woman with whom he is ashamed of being seen in public. This is a far cry from insisting on only dating  ‘knockouts’ or ‘hunks’. For some reason many men like thin. Of course they also want those children right away. So, within a few months the woman puts on the pounds, has trouble getting them all off after the pregnancy and is soon pregnant again. So much for thin. Don’t misunderstand, there must be some chemistry, some attraction. However, unless there is a very real turn-off involved, at least meet and go on several dates. People do grow on each other. Someone who was minimally attractive as a stranger may be quite acceptable once you get to know him/her. It is a given that you know, like and respect any number of truly unattractive individuals. Many are married. Because you’ve gotten to know them, in a very short time, you see beyond ‘skin deep’. Beauty is in the eye of the beholder. An old friend of mine used to spend hours describing in detail the woman he was looking for. In short, she was to be drop dead gorgeous, absolutely brilliant, have a sparkling personality etc. etc. yada yada yada ad nauseum. We went our separate ways. Some time later he became a Choson. Over the phone he couldn’t stop raving. Events conspired so that I was unable to meet her for some time but I couldn’t wait to be ushered into the presence of these wonder- women. When we finally met I was not overcome by her beauty, dazzled by her sparkling wit nor overwhelmed with her brilliance. Nice woman but after that build-up I was disappointed. The point is that my friend thought of her as an all around ‘10’, still does 30 years later and that’s all that matters. It is for this reason I advise people not to tell the Shadchan that you want a ‘beautiful’ date or only ‘handsome’ men will do. What the Shadchan thinks is ‘beautiful’ or handsome’ is quite likely not what you had in mind.

I was advising one young lady a number of years ago who was clear on only wanting a guy who was at least 6’4”. In the course of conversation I asked if she would go out with someone who met all her other standards but was only 6’3”. She hesitated and then said yes. So I went to 6’2”. Again, all else being equal, she said yes. Over the course of several conversations I gradually got her down to 5”8” (She was only about 5’4”). A far cry from insisting on tall and being unwilling to even meet anyone shorter. PS. Her husband is not 6’4”.

Age – within certain boundaries age is rather unimportant. Too much disparity is foolish, of course. Younger couples tend to have a two or three year spread of male older than female. This is due to the fact that young women tend to be far more mature than young men. In older couples, age is far less important. No where is it engraved in stone that the man must be older than the woman. Don’t get hung up on this. Everyone knows at least several couples where she is older than him, taller than him or making more money than he is and it works. (Even Ken is two years younger than Barbie, she makes more than he does as well and look how successful they’ve been.)

Biological clock issues, however, can be real since an older man can still have children. All the more reason why women in their mid-thirties are really pressured yet caught in a bind. It seems no matter what the woman’s age the man wants someone younger. When women are in the 37- 43-year age range they face a very real problem.

Women tend to either conceal their age or outright lie about it. To some degree they are forced to do so or they will get fewer dates. This is perhaps the one area where my insistence on honesty may be hedged.

-Chemistry and attraction should be there although not necessarily on the first date. Don’t expect firecrackers, the New York Philharmonic or an immediate swoon. Love at first sight is possible, rarer than you might think, and simply not realistic. Once again, take the time to get to know the other person.

So what do you reveal, what may you conceal and until what point can you keep skeletons in the closet? If you’ve been on the dating scene awhile some, or all, of that information has probably been disclosed before in prior relationships. If so, your chances of keeping it a secret become slimmer. The circles in which we operate are limited. Information is freely traded among both men and women. Your ex-dates are likely to tell all to your potential dates including their own opinions and their read on your personality. Well-meaning Shadchanim can say too much too soon. Thus, it becomes important to utilize PR techniques to turn lemons into lemonade. When I receive a “check-up” call wanting the lowdown on a potential Shidach I am careful to give minimal information and to keep it positive and upbeat. I also keep the call as short as possible. Let them go out. Why should I spend an hour on the phone with deep background checks when they may decide in the first five minutes of the date that its no go? If the first date goes well there will be time for further “checking”. Again, unless one knows of information that clearly mitigates against permitting the relationship to go forward the operative principle is – keep it to yourself!

What information must be revealed and when?  This important question deserves careful analysis. There is clearly information that is unfair to hide even up front.  If you are a convicted serial chain saw killer (pardon the heavy-handedness) you must make that known immediately. A couple of parking tickets aren’t worthy of mention. Somewhere between these extremes will be a comfort zone. I generally feel that most pertinent information should be disclosed by the third date. It is also important to understand that it is always better for the information to come from you rather than an outside source. There are issues which I feel can wait a little longer, but if that is the case, this disclosure should be made in a session with a discrete third party present. This hopefully mitigates the information, allows for calm discussion and will hopefully not be the end then and there.


– Medical problems

– Genetic issues

– Prior broken relationships (broken engagements or divorce)

– Dysfunctional family background

– Evidence of alcohol or drug abuse

-Psychological or psychiatric problems.

– Anger or rage simmering below the surface

– Self-centeredness, over-inflated ego

– Legal binds

Even some of these issues are not 100% red flags.  What you and I may find intolerable others may find very workable. Should you, or should you not disclose that you’re on medication? It all depends. If you are unable to function without the medicine, at some point you need to inform a potential spouse. If you are taking a low dosage of some medicine to ‘take off the edge’ but are fully capable of functioning without it, there is no need to make this an issue. It can be mentioned later on, if at all, casually and of no real importance.

Medical issues are tricky. Essentially you need to put yourself in your date’s shoes. Would you expect to be told this information? If you weren’t informed what would your reaction be? (This is a good test regarding all information)  Amongst other things, this one should be discussed with your Rav.

Genetic issues fall into the same general category as medical issues. Speak with your Rav.

Do you have therapy in your past? Disclose if it’s heavy issues, long term and especially if it is ongoing. Don’t disclose if it was minor and temporary.

Previous marriages and broken engagements need to be disclosed. In most cases this is up-front information. It will also require some discussion. Don’t fall into the trap of making it all out as the other one’s fault even if it was. This sounds phony and self-serving. It also makes you out to be one who can’t take responsibility for your own actions.

Divorce not final yet? Having your pants sued off? Disclose! A long, dragged out, messy divorce should indicate that you’re not ready to start dating yet. There are exceptions but it’s only fair to your date that he/she is aware of the situation. Lawsuits can have legal ramifications down the line to a new spouse beyond the obvious. Again, full disclosure is mandatory.

If you grew up in a dysfunctional home and/or currently have a poor relationship with your family the question that you need to ask is “Have I resolved these problems to my own satisfaction?”. Resolved problems recede somewhat into the background. They never disappear and have a tendency to re-emerge later on. The only marriage you’ve seen up close is your own parents’. They may or may not have been good role models. The problems they had (or are having) are going to be issues you need to face. Since most people tend to marry someone similar to dear old dad or mom, the problems will also tend to be similar. Generally speaking, if your parents fought alot, this will be an area of concern for you. Children who were hit tend to be hitters. Children who were screamed at tend to become screamers. Or else they bend backwards so far the other way that no balance is achieved.  The issue needs to be discussed. However, if you have unresolved problems, depending on their severity, you probably need to seek therapy before committing to any relationship. An older professional single spoke with me at a singles weekend having trouble dating. It soon became apparent what the problem was. He became a professional to please his mother but hated his job. He also had to call her twice a day or she would be angry with him. Uh-oh!!! I advised him to tell his mother, respectfully but in no uncertain terms, that he would be calling once or twice a week, no more, and that he would no longer be reporting every detail of his life to her. I also told him to get out his resume and start looking for a job that he enjoyed.  One year later, at another weekend, this man comes rushing up to me, grabs me around and thanks me for saving his life. He had followed my advice. It was difficult at first but Mom eventually came around. He had a new job that he loved and for the first time in his life he was happy. He was now (probably) ready to date.

Bernard Baruch was a famous Jewish Washington lawyer, an advisor to several presidents. He was known for his promptness. On one occasion he was invited to a dinner party which began at 7PM. The host was prepared to greet him but 7PM came and no Bernard Baruch. Several minutes later the doorbell rang. It was the chauffeur tendering Mr. Baruch’s apologies. He was sitting in the limo downstairs arranging his conversation for the evening.

Unlike most of us, he had specific information to relate to certain people and specific information he needed from others. When you are set up with someone there will usually be at least one initial phone call followed by a date. Be prepared. What information should be given and received on the phone call. What do you need to find out on the first, second and third dates. Which information do you need to impart at those times? One error made by those new to dating as well as many veterans is an attempt to get all there is to know up front. Treating your date to the third degree is a sure-fire way of avoiding any future dates with that person. Similarly, when word filters back that you’ve called a dozen people to ‘check up’ even before the first date, it’s a turn off.

Evaluate – don’t judge! You are looking for your best friend. Best friends don’t judge one another.  When you go to buy an Esrog and minutely examine it for flaws that may be okay. Do not subject a date to this level of scrutiny. There will be flaws. Everybody has them. Search intensively for the good, the positive, what is right about the date.

You’ve been in relationships before. In some cases, there was a single criterion that was the ‘blocker’. Perhaps it was, perhaps it needn’t have been. In the final analysis, only you can make that decision. Don’t try to fool yourself that you will eventually, if you keep at it long enough, find your ideal. That’s fantasy. Reality is that you are not perfect, nor will your partner be. Every close relationship survives the shortcomings of the other side. This is true of close friends and close family members. Marriage is not only not an exception, it is the rule. It would be rare to find a married person who could truthfully say that their spouse and their ideal are one and the same with zero faults, no shortcomings, and never a disappointment. Those who can make this statement have indeed found a gem but they have also, to a large degree, accommodated themselves to their spouse, perhaps without even realizing it. Thus, what might be a source of irritation to another couple is seen in a positive way in this relationship.

Let us see if we can develop a general scenario to aid singles, Shadchanim, rabbis and well meaning friends on the protocol of sharing information, avoiding Lashon HaRa and actually helping.

Setting up a Shidach

-Don’t set up a Shidach simply because he is male and she is female and both appear to be alive. Give it some thought, discuss it with somebody who knows the other one or, even better, both of them

– On the other hand, don’t ‘deep six’ a possible Shidach because you “think” they may not be compatible without excellent reason. They are adults. Let them make up their own minds.

– Be very careful about what information you share. Most of what you say will be Lashon HaRa, Rechilus or Motzay Shem Ra. Unless the information is crucial keep it to yourself!

–  Give out information sparingly.

– If he’s asked for thin and you think someone ‘plump’ is for him, please don’t set them up on a date. That’s doomed. Invite them both for Shalosh Seudos, perhaps with some others. Let them meet in a non-threatening atmosphere. First seeing her as a person may enable him to get past the weight issue. Then, if there’s interest a date has a greater measure of success.

Checking out the other person

– Identify basic Hashkafa. Be very careful since semantics can be tricky. What one person thinks of as “Yeshivish”  or “modern” may not be your definition or that of a potential date. For the right person there will be a lot that is negotiable.

First phone call

– The sole intent of the first phone call is to determine whether potential exists. At this point a single unthinking comment can end it on the spot.  Rather than try to be insistent on information gathering, keep the conversation relatively light, friendly and focus on nailing the first date.

– Some questions need to be asked, you’ll need to impart something about yourself as well.

1- Avoid “Tell me about yourself.” This is not a job interview.

2- “Where do you work?” “What do you do?” are safe bets. This question should also give you a clue as to educational background and level. It will also give you some hints about financial status. Where did you go to school? What did you major in? What courses did you like most? Least?

3- “Do you have any other interests, hobbies or talents?” This question may assist the man in deciding where to go on a date. It also will provide conversational material on the first date. If you know zero about Gothic architecture but that’s her thing, do some homework. It will be appreciated.

4- “What are some of your life goals?”  Deep enough yet not prying. It also opens avenues for discussion. Continue with “Mine are….” Switch off asking first and then offering something about yourself with offering first and then asking. Balance talk of you carefully with talk of your date. A lack of balance makes you either too egocentric or too nosy.

5- One possibility would be to offer her three choices of where to go for a first date. Not every woman will like this approach; some will leave it up to the guy. Ladies help out here. I’ve often heard of a woman leaving it up to the man and then complaining about his choices. Mind readers are hard to find.

6- Hashkafa issues should be broached. Stick to broad outlines. Getting too specific too soon is counter-productive. Generally the gray areas will be Chalav Yisroel, TV, black hat/ kippa sruga, covering hair and commitment to learning. View them as negotiables not dead ends. Much of life means trade offs. Don’t discount an otherwise good match on a point that can be discussed further. A friend was dating. He desired a woman who would cover her hair. He eventually found a great match but she was adamantly opposed to covering her hair. Frantic phone call, “What should I do?” I suggested that he not make an issue of it at all. Proceed slowly and somehow casually mention that covered hair is important to you. She was so impressed that he didn’t make an issue of it that she offered to cover her hair whenever they visited his friends. Second “How do I handle this?” phone call. Again, same advice. She was so taken by his ‘understanding’ that she upped her offer to cover her hair in the house – but not at work. By this time he’d caught on, didn’t say a word. By the time they married she had come all the way around. Although you can’t count on this always happening, you’d be pleasantly surprised how much people are willing to give up or take on to make a relationship work especially if they see that it’s a two way street. If you push too early in the relationship you could be endangering your position. As you get to know one another better, trade offs become easier, more palatable and will tend to make more sense.

We’ve all heard “Don’t expect people to change”. That’s true in regard to basic personality type. Most other things are negotiable and if handled well can become a plus rather than a minus.

First date

1- Men – Find out from the Shadchan if she has real preferences. Some women expect a fancy restaurant, others may be more impressed by someplace different. You can figure that they’ve been dating awhile and have probably ‘been there done that’ so use your imagination. Women – give the Shadchan, or your date, some clue as to what you expect, would like or don’t care for. Everyone involved needs to make the process easier, not a guessing game. If you prefer casual – say so.

2- Some people are garrulous, others more silent. You must figure that the burden of the conversation will fall on you. Like Bernard Baruch, be prepared.  Discussing the weather beyond a passing comment won’t fly. Politics isn’t what you are there for. The situation on a date is patently ersatz. Both parties are somewhat nervous, on their best behavior and trying to make a good impression. Cut each other a little slack. It’s difficult to break the ice. Many people are not good at small talk. Work to make your date comfortable.

3- Don’t expect to be entertained. Placing the burden on the other person is unfair. Show some excitement. Nobody wants to spend several hours with an obviously bored, or boring, date. Either way it’s over.

4- This is the time to begin trading information about attitudes and opinions on various subjects.

Is she a vegetarian? Does he expect to go to the Bais Medrash every night?  Are you excited about your job? Are you a saver or spender? Tell your date a little about how you handle finances. Ask how they handle there’s (be careful not to seem to be prying). Share some family info about mom, dad, and siblings. Get some feedback about his/her family.

5- One sure-fire method for jump starting a flagging conversation is to ask for some help. Everyone just loves to help and to offer advice. Choose what you’ll request with care. It’s too soon to get too personal.  It may be a situation at work, an etiquette quandary, or help on a project. Don’t drag out the telling too long. The point is to elicit response. The nature of the advice given is another indicator of the way your date thinks.

6- Try to picture yourself living with this person. This is a great mental exercise. Try hard to picture it working. If you can realistically picture it, pursue, pursue, pursue.

Second date

You’ve spoken on the phone, had a date, perhaps spoken on the phone again. By now you know some important things about the other person. You’ve done some checking. The second date is crucial in a way differing from the first date. Obviously, there was enough interest on both sides to want to continue. Conversation on the second date should pick up on prior topics. There will be a need this time to give and receive more substantial information. Careers, where you see yourself living, depth of commitment to Yiddishkeit are all necessary discussions. More in-depth analysis of potential problems and issues. Show your sensitivity. Even if you find something shocking, keep your reaction cool. Rather than prying for further information, or mentally calling off the whole thing right now, commiserate, show some sympathy and understanding. In retrospect, the issue, whatever it is, may seem less calamitous the next day. Buy yourself time to sleep on it, talk it over with your mentor and then decide. Many otherwise good Shidduchim could have worked if one side had been less precipitous.

Third date

Protocol nominally assumes that the third date is the make or break one. Proceeding beyond this point generally indicates some real interest on both sides. After this date the Shadchan is generally no longer used a middleman to arrange dates, express feelings etc. By this time, with the exception of very few issues of importance, most information should have been traded. Any real skeletons left in the closet had best be revealed by a third, discrete party, in person, at a meeting set up expressly for this purpose.

Fourth date

There should no longer be any skeletons in the closet. It is, or will soon be, time to bring up timeframes. He may want 15 dates before proposing but she’s expecting to be asked next week. She may want to have a two-year engagement while he’s figuring on two months max.

If you have gone on a number of dates and both are somewhat interested but nothing seems to be happening it might be best top take a break. Don’t see each other or call for several weeks. This breather may give both of you some time to determine whether you wish to go forward. If yes, go for it. If no, the breather will have made breaking up somewhat easier for both sides.

Ideas for dates

– Hotel lobbies and airport terminals are okay, not very imaginative. Probably not a good idea for a first date.

– Restaurants can get very expensive but do offer variety and a relatively quiet place to talk. If you go the pizza shop route you’d better have somewhere else in mind as well.

– Mall walking offers an indoor, public area. You can browse through stores, sip a coke. There are places to sit and many malls have interesting things to do as well. It’s a cheap enough date that you can splurge and buy something from those little kiosks just for fun. A stuffed animal, cute coffee mug, inexpensive silk scarf, key ring whatever. Be thoughtful. Probably better for a second or third date.

– There are craft shops where, for a fee, you can make ceramics etc. It’s different, fun, allows you to talk and the ceramics are great props.

– The zoo or amusement parks are a change of pace.

– Historical mansions

– Paddle boating in the summer.

– Ice skating, roller-blading if both are athletically inclined.

– A summertime picnic in the park. (Do it up right with wine and two crystal goblets or at least two plastic ones that are supposed to look like crystal.)

– Museums are great bad weather day alternatives. (Watch out for potential Tznius problems in art)

– The Aquarium.

– Large craft fairs.

– Browse antique shops

It’s no go  — Breaking it off.

When either side has determined that this is not the one a great deal of tact, diplomacy and sensitivity is required to spare unnecessary hurt to the other party.

After the first or second date, it is best done through an intermediary, typically the Shadchan. While it may not be totally necessary to give a reason, the Shadchan will want to know why to help you on future matches. It is might also be helpful to the other party to know why, particularly if they’ve made a faux pas or have some defect that can be corrected. It is also extremely helpful to you to clearly understand why you have chosen not to continue or have yourself been rejected. Over a span of dates you may be able to discern a pattern. That pattern may be very revealing.

After the third date, depending on the nature of the relationship, it may be broken off either through the Shadchan or personally. Beyond that point, any break up must be done personally (with few exceptions). I would almost always advise this to be done face to face. The telephone is a poor way to break this sort of news. Not everyone will appreciate being hauled out on a date for the sole purpose of being told that you no longer wish to continue dating him or her, but the alternative is cold and unfeeling.

In any event, it would be very helpful to keep a notebook of prior dates. Each entry should list name, month and year of dates with this person, where you went, name of Shadchan, relevant phone numbers, some pertinent information about the dates, who rejected whom and why. This record will be very helpful in determining whether you’ve already been out with somebody when a Shadchan calls. Often someone who you rejected two years ago may be worth another shot now. And, last but not least, you may be able to pick up patterns, as we pointed out above.

Long distance dating

If you’ve been set up with someone who lives any real distance away the protocol for dating changes. Since both time and money become factors it is much more important to do additional up-front checking prior to the first contact. Unless you, or the other person, will happen to be visiting the other city anyway, in which case a date is not inappropriate, initial contact will be by phone. Clearly more than one or two phone calls are in order prior to either committing to travel. Just as clearly the telephone is not a good way to form first impressions about another person (E-mail is useful but even less effective). All of the visual inputs, body language, facial expressions etc. are missing. Having little choice, you must utilize the phone in the most effective manner possible in determining if this is a real Shidduch or not. Once you are past the first meeting the phone and E-mail can be very useful in fostering the relationship. Bear in mind that phone conversations are more difficult to maintain with someone you barely know. All the more reason to have prepared questions and topics beforehand. On the plus side, you can have written notes in front of you and can jot down thoughts as you talk.

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