Website sponsored by Mr. & Mrs. Malkiel Goldberger in honor of their precious children | 443.955.9887
Website sponsored by Mr. & Mrs. Malkiel Goldberger in honor of their precious children | 443.955.9887

Yated Shidduch Forum 6/9/17: Long Dating Saga’s – How Long To Keep At It?

To The Esteemed Shidduch Forum Panelists:

Many of us have had some long dating sagas. It seems that the common factor in many of them was that there was something bothering either the girl or the boy since the beginning, but no one, not the girl nor the boy, wants to let a good shot slip through, so they give it their all. But until when? 

A boy goes out with a girl, something is bothering him, but he wants to see if he can get over it, so he continues to date her. He gets to know her better, he appreciates her, and they continue to date. She thinks it’s going somewhere, they go out a number of times, and he says no… because he can’t get over the initial issue that bothered him. The girl feels like she was schlepped along, and the boy probably doesn’t feel all that great either. The same can be said for a girl dating a boy where something is bothering her… 

I do think that proper communication between the boy/girl and the shadchan is vital. Both the boy and the girl have to know where the other one is holding. And I do know that shadchanim are not always getting complete feedback from both sides.

With that being said, here is my question: Until when do you continue to date someone because you appreciate their goodness, but there is something there that is not moving things forward? We take dating seriously. We don’t want to just give someone two dates and say no. We want to work through things and see if there is potential. How much is considered giving it your all, and at what point are we dragging out a saga that should have been over after a third or fourth date? Until when do you say, “I’ll go out one more time to see if I can get over ___”?


While a definitive answer to your question might appear useful, inasmuch as human beings are multifarious creations, and further being that pairing two human beings together exponentially complicates this reality, making such decisions is more art than science.

Each circumstance must be evaluated based on its own variables and what course of action will most plausibly benefit the shidduch. And, in the end, it is not truly possible to know if sharing a concern was a good idea or a poor one, or if a shidduch that ended after seven dates should have ended after four, or shouldn’t have ended at all. Only HaKadosh Boruch Hu is all-knowing, and second guessing ourselves after the fact is only worthwhile if there is a lesson to be learned for the future.

What I believe is most valuable, then, is to present an overview and framework for approaching these types of situations. Given the generalities, each person must decide what is the most sensible mehalech for their circumstance.

First, the question of what information should be passed on to the other side when there is a concern, and what information is best not shared, must be addressed.

And the answer is, it simply depends on whether or not it is a concern that is beneficial to share and discuss. For example, if one of the parties is not attracted to the other, or finds them to have a character trait that is irksome, that is quite obviously not a topic ever worth discussing. Although these concerns can change, they do not change because the singles talked it out and reached a conclusion together.

If there can be no benefit from having a conversation, or from having the shadchan relay certain information from one side to the other, that is something that each single must figure out on their own, or with advisors that will keep the information completely confidential.

On the other hand, conflicting expectations, hashkafos, or life goals are very much worth discussing, and should be openly approached, at the appropriate time. For example, one might hope to open their Shabbos table regularly to the needy, or in an effort to show the beauty of Shabbos to those who are not Shomer Shabbos, while the other person may prefer to have most meals limited to family and direct their attention towards the children, b’ezras Hashem. Or, one may have envisioned marrying into a certain kind of family, and, while the interpersonal aspects of the shidduch are spot-on, there may remain misgivings about the broader family picture.

Metchila, it must be established that the rapport between the singles is comfortable enough to weather in-depth conversations about topics which they feel strongly about, yet heartily disagree. For some, that might be on the second date, and for others, that might not be until date four or later. It depends entirely on the nature of the person and how the shidduch is progressing.

No one should feel that something is wrong with them if it takes them longer to reach that point. There is no better or worse, only different personality types and different progressions due to different pairings of personality types – and neither type is indicative of the quality of a marriage to come.

Once that point has been reached, it is imperative for the two single people to openly and honestly broach whatever significant concerns remain, in order to discern whether or not the shidduch still has potential.

Which leads us to our next question: At what point should one bow out from a shidduch which is not firing on all cylinders?

To borrow from the previous examples, in the cases of attraction or character traits, we could fill entire issues of the Yated with names of happily married couples where one person started off un-attracted to the other or was bothered by a character trait, and, as the dating continued, soon found themselves making a 180-degree turn. Within the scope of a healthy relationship, as connection increases, so can attraction, while bothersome traits often dissipate, or even become endearing.

However, at the same time, we cannot pretend that these aspects don’t matter, and there comes a point where one must say, “I see the many mailos of this person, but these issues do not seem to be changing.” Again, there is no exact number of dates as to when this should become clear. Rather, when one reasonably feels their concern isn’t likely to improve, despite giving it a fair shake, that is when a decision should be made.

As far as opposing expectations, hashkafos, or life goals, through discussion, one must discover if common ground can be reached, and if a happy, healthy home can be built, given the diverse approaches towards matters of real significance.

Let us not fool ourselves into thinking that there exists a marriage where both husband and wife are in lockstep regarding every prat u’prat that carries weight. As Rav Wolbe ztz’l clearly states, the very definition of “shalom” is making peace, and growing, through hisnagdus. Shalom bayis doesn’t mean that conflict is non-existent – that is merely a reflection of two people who haven’t yet actualized keirvas hada’as v’hachaim. Shalom bayis is only achieved when conflict has been revealed, and the gap is then successfully bridged.

Bridging the gap does not mean saying to oneself, “I am not really ok with this, but I can live with it,” although there are times when that is necessary in a relationship. What it means is, each single respecting and appreciating the value of the other, and through being open to one another’s viewpoint, reaching a new and even higher conclusion, as a result of the value that each person brings to the table. That is what brings the Shechina into a home.

The same is true of dating. One should not be looking for a shidduch where there is no disagreement. Rather, one should be searching for someone with whom disagreement can be had in a healthy fashion, to the attainment of mutual growth.

As such, it is only after getting teiff arein into the impediments that one can distinguish if they are impassible, or if they will form the bedrock of future growth.

Granted, it may take a fair number of dates to reach that conclusion, but that is the nature of finding a spouse. Dating is not meant to be inherently easy. It can be easy, hard, or somewhere in between. For some the hardship comes in the form of pain experienced as a result of not getting dates; for others, it is the frustration of lots of dates, but none that show a hint of potential; and, for yet others, it is the agmas nefesh of ambiguity when the potential of a shidduch is uncertain.

May The Melech Chai Olamim, d’migalyun Lei tamrin, lend tzachus hada’as to you, and to all those who find themselves unsure about a shidduch, and may the ensuing clarity lead to emesdikeh nachas and hatzlacha.

Related Posts

Leave a Reply