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

Yated Shidduch Forum 11/8/19: How Do I Cultivate a Meaningful Relationship During Dating?


In the dating process, how does one turn a superficial, casual relationship into a real, deep, close one? I dated someone for a while and really liked him, but my biggest concern was that our relationship was hardly deeper or more personal on the 7th date than it was on the 2nd. I felt that I did not know much more about this young man and there was almost no point in continuing.

One of the problems could be that I am a more private person, so I have a difficult time opening up and revealing my thoughts to others. 

Any tips for the next time I go out? 

Thank you. 


As positively fundamental as is the objective of fruitfully fostering forward-moving rapport, it remains a realm that is equally subjective vis-à-vis finding success, or lack thereof. Struggles may result from numerous origins; be they matters of circumstance, choices of conversation, or unique attributes. Accordingly, provided with but a fairly brief narrative, I am reluctant to offer a categorical conjecture as to why this experience has transpired. Consequently, I would like to discuss three common impediments which I have observed in this department, with hopes that doing so provides some degree of prospective benefit.

1. Dating is essentially the most concentrated act of labor with respect to creating interpersonal interaction and nurturing new bonds. And no different than any other endeavor in life, it is a finite skill which is not an innate derivative of any other particular proficiency one may already possess. Furthermore, we have a system which regularly exacts imposing and extreme pressure on daters to make life-altering decisions in an unduly and arbitrarily truncated duration. Daters are also oft bombarded with unsolicited, unending, apocryphal, and even conflicting instructions regarding how to achieve victory in this discipline, further compounding the challenge at-hand. 

Correspondingly, I cannot overstate the value of expert and experienced dating mentors when one is in need of navigating obstacles to generating deeper affinity and kinship. These advocates can aid immensely in detecting and revealing blockages, and implementing tactics to prevail over them. Without exaggeration, mentors have brought immense relief and clarity to myriad daters, and have ushered countless shidduchim to fulfillment that were previously presumed unsalvageable for this exact cause. Additionally, while there is typically advantage to more than solely one point-of-view, it is essential to limit one’s primary source of guidance to a small circle of trust, all working in tandem. A cacophony of scattered specialists is generally overwhelming and counterproductive.  

2. Sometimes, people just need more time. Provided no one is being led on, and that the shadchan is unequivocally informing both daters that though there are overall positive feelings, there persists a hitherto absence of the requisite measure of emotional attachment, it is absolutely acceptable to proceed with additional dates to see if that barrier can be overcome. Indeed, I know of many couples who, under astute counsel, extended their courtship beyond the norm, were able to produce the level of interrelatedness needed, and subsequently went on to build wonderful lives with one another. There is no magic number, and until one truly feels there is nothing left to unearth, going on more dates than would be the standard is often an excellent solution.

3. When a couple goes out a handful of times because they very much like one another, such is not an incontrovertible indicator that they have pinpointed their future spouse. It simply might not be the one. There are many people whose company one may enjoy, and with whom they are compatible in many ways. Nonetheless, it may not be the companion one can spend the rest of their life with as husband and wife, raising a family, and continually cultivating an ever deeper marriage. This happens with great frequency, and is perfectly normal. Hence, one may need to rely on their gut feeling, and trust when something inside is telling them that while they are in the midst of dating an outstanding person, it is not the outstanding person they are meant to greet under the chupah. Irrelevant to how many good dates have transpired, if one senses stark stagnation, notwithstanding attempts at solution made thus far, and has no rationale to deem this will change, it may be the end of the road.  

Lastly, it must be stated that careful reflection is vital to discern which of the above issues, combinations thereof, or others entirely, are at play. For example, how often is this happening to a dater? Twice, or twenty times? And if the latter, while a markedly excessive amount of these occurrences is often a reliable indicator that it is crucial to enlist a mentor, it may also turn out that all twenty of those people were not the right fit. It could very well be that despite the regularity of this hindrance, one is not want in their capacity to build a relationship; they merely have not yet met that person with whom to build it. 

Does one have epistemically substantial and plausible certainty about the magnitude of their private nature, based on their past, to deduce that this sufficiently explains away their dating impairment, or is this problem utterly new territory? And even if one’s quality of reticence is not wholly novel, being relatively private is not an inherent preclusion to developing closeness. There are many deliberations and contradistinctions to be considered, and one is best served by asking these questions of themselves as they proceed with identifying how best to approach the setback, and fittingly attain a suitable solution.

May the Matzmiach Yeshua impart lucidity to all the single men and women in Klal Yisroel, along with the capability to discover and connect with their true and apposite counterparts in building a magnificent bayis neman b’Yisroel.