At what point should parents of a boy and a girl speak about money and support during a shidduch process? In our last two shidduchim, we didn’t do so till after our children were already getting engaged. In a sense, it was already too late. There were certain things that we would have wanted to be ironed out earlier, but it almost seemed like there was never the right opportunity for that to take place. Is it the shadchan who should be asking when we want to talk about the finances? What is the prevailing custom when it comes to these things?
Once a couple has reached that captivating juncture where there is a mutual longing and commitment towards marriage, there is very little, if anything at all, that will instigate divagation from that path, or that can stand in the way of an unwavering determination to see their ultimate goal carried out. Indeed, there have been many instances where a complication which would likely have presented as an insurmountable barrier at the research stage, or very early on in the proceedings, becomes but a blip on the radar when it is only discovered after the finish line is in sight.
That is to say, it is rather apparent that our capacity to creatively solve problems and unearth extraordinary solutions to obstacles exists in direct correlation with how badly we want something to happen. And though every dater wants with all their heart to stand under the chupah as soon as humanly possible, there is no comparison between the degree and intensity of that yearning before one knows whom they want standing there with them, and after having acquired that knowledge with clarity and certainty. Nonetheless, it would be grievously irresponsible to suggest that all daters walk blindly into the process, assuming that once enough compatibility and connection has been cultivated, they will be assured of their ability to overcome all plausible hurdles. Such a supposition is sure to backfire with great regularity, and would put daters in an unfair and painful position time and time again.
However, to presume that one could preconceive every possible challenge which may unfold is both unrealistic and impossible. And given that certain topics are critical for some families and entirely irrelevant to others, shadchanim cannot be expected to keep a list of every potential issue, and then run that list by both families for discussion each and every time they redd a shidduch. Doing so would be inordinately onerous and highly counterproductive, and could threaten the viability of otherwise excellent shidduchim. Even the area of support, which would seemingly be applicable to anyone and everyone, in reality, is not. For those who have already prepared on their own how finances will be addressed, or who are generally less apprehensive about the fiscal aspects of marriage, they may be in no rush to engage in an awkward conversation about a consideration which does not weigh heavily upon them. Conversely, for many others, a lucid plan of how bills will be paid is a top priority in want of attention.
Accordingly, it is my opinion that the burden of deciding in advance which specific subjects ought to be ironed out from the get-go falls on the daters and the families themselves, and I do not believe there are any concrete rules regarding when to broach money, or any other particular shidduch-related item. As such, each family must attempt to identify the themes which they feel require concerted focus at the outset, whatever they may be, and take the initiative to delve into them. Of course, one is more than welcome to request that the shadchan assist in bringing up delicate content tastefully and with propitious timing, but it must be the family that gets the ball rolling when they feel the need to work out any given concern.
Yet, lest one fear that such an encumbrance is too untenable to bear, I am wholly convinced that the most we can ever do is prepare to the best of our abilities – without going obscenely overboard – trusting that our hishtadlus will merit us the Hashgacha we all have in store. Provided we do our due diligence, and that each individual genuinely endeavors to attend to the matters they feel are most important to them, I remain fully confident that HaKadosh Boruch Hu will sort out the rest, according to His unfathomable wisdom and His unimpeachable design.
May the Misgav Baadeinu watch over us all, and never refrain from bestowing upon us His endless bounty.