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Yated Shidduch Forum 7/9/21: Closing In On 30 and Totally Confused. Please Help


I’m a twenty-seven-year-old boy and I have been dating for over five years. At this point, my head is spinning. I have been out with so many girls, and after every time, I find myself more confused that I don’t even know what I am looking for. I believe that I have to go back from the very beginning. Can you please give me guidance? 

How do I know what girl is right for me? What qualities will help build a marriage and what not? How can I tell in a date if she will make a good marriage partner? Does she have to be exactly on my level in hashkafah? Does she have to enjoy the same activities I do? Do I have to agree with everything she says? If I love taking exotic vacations all over the world and she hates flying, is that a reason to say no? I really hope you can give me clear-cut guidance as to what to look for and what not to look for.


While each and every one of these questions is certainly valid in its own right, and even foundational and fundamental, the sum total of all of these subjects, presented in bombinating and rapid-fire succession, reads to me as follows. “I am closing in on 30 and I haven’t the faintest idea how to date. Please help.” 

Accordingly, and unfortunately, given the magnitude of the dilemma, I do not believe it possible for me to offer even a semblance of “clear-cut guidance” that would in any way resolve this overwhelming ambiguity surrounding the entirety of the dating enterprise. Fortunately, however, these difficulties are far from unusual. And as the very real issues of gripping indecision, hesitation, confusion, and diffidence have become exponentially more common in shidduchim, the world of dating coaches and mentors has truly flourished over the past number of years. Indeed, there are a great many people who have sharpened their skills to near perfection within the realm of providing clarity and purpose to daters as they venture into and traverse the dating landscape. 

Thus, I cannot state emphatically enough how vital it is for those who find themselves utterly and importunately lost in a mire of doubt when it comes to shidduchim to reach out and connect with an expert in the field. Such guidance is optimally given over one-on-one, and tailored to the needs and nature of each individual. When the irresolution is so all encompassing and the malaise is so deep, no amount of generic advice or going it alone will suffice. The balm best applied, in such a scenario, is that of personal attention and direction. 

May the Oteh Ohr Kasalma spread forth His providence, and illuminate the path of prudence before all those who yearn to travel the hallowed road towards matrimony.