I’m a single girl in my early twenties. Boruch Hashem, I get dates often enough. My dating has been fairly typical, with some mutual no’s, some good tries, and some “no shaychus” dates.
The thing is that I have a family situation. It is not something that has to do with me personally, and it is not something that most people know about my family. I’m finding that it’s holding me back from dating well, because I constantly feel like I’m on guard and like I’m hiding something. I am happy that boruch Hashem people don’t usually find it out when they check out my family and that my secret is safe, so to speak. But I feel like I can’t go much past the first and second date superficial conversations because of it. (I’ve dated boys four times or more, but it didn’t go anywhere.)
Sometimes I wish I can just tell on the first date so that I have a chance at open communication, but I was advised not to and I don’t think it’s smart, because then the boy will think of me as my family situation before getting to know me. On the other hand, I feel like a boy can’t get to know me anyway if I am so on guard.
That a single man or woman may be concerned or disconcerted about an idiosyncratic or stigmatizing data-point derailing their shidduch opportunities – be it particulars related to themselves, or their family – is not at all uncommon. Nonetheless, in most instances, this quandary does not interfere with one’s ability to date successfully and comfortably, or prevent them from presenting an honest and deep representation of themselves. Rather, it is generally a matter of delicate planning and logistics, and deciding when to share this material.
With respect to determining when to confide sensitive potential complications, the hadracha I have received from rabbonim is to introduce such disclosures at the mid-point, of sorts. That is to say, after enough rapport has been established so that any conceivably damaging revelations can be counterbalanced by the positive and appealing aspects which have been conveyed, admired, and appreciated by one’s counterpart. However, such elements should not be concealed until engagement draws imminent, thus putting the person one is dating in the highly unfair and unjust position of having been led nearly to the point of no return, before being able to include pertinent, recondite, and plausibly unsettling complexities in their deliberations. To be clear, one does not arrive at this juncture after any set amount of dates. It is entirely subjective, and is based on the nature of each unique couple, and the progress they have made together.
However, based on the narrative provided, it seems quite clear that apprehension stemming from any measure of exposure of this familial information, which has been deemed as harmful, has resulted in a colossal barrier. Namely, it has precluded the development of any real proficiency to be appropriately open with the person one is dating; it has hindered the broaching of meaningful topics of conversation; and it has entirely inhibited the cultivation of a connection beyond the shallowest and most surface levels of familiarity. Consequently, I believe it is absolutely crucial to employ the services of an expert dating mentor, or perhaps a professional therapist.
Doing so should allow one to better understand why this roadblock is manifesting itself to a degree so immensely intense and profound, and has become an undeniably insuperable impediment. Accordingly, aided by, and armed with, this newfound knowledge of self, one will hopefully become capable of generating the tools and skills necessary to continue dating without this enormous weight forestalling their aptitude to date competently and expressively. And, most importantly, it may allow one to truly and peacefully present the sincerest and most authentic version possible of who they are whilst dating, nurturing the relationship at the proper pace, and divulging that which must come to light at a time which will not inherently thwart the shidduch.
May the Matir Assurim release those in shidduchim from any and all obstacles – internal or external – which obstruct them from attaining their ultimate goal of marriage, building a beautiful Jewish family and home, being fully at ease with who they are, and wholly cherishing the intrinsic value that they and their family possess as a tzelem Elokim.