For years I have been urging the greater Torah-observant community to discard the sort of questions that are typically asked of singles in the shidduch scene. (By now it is probably unnecessary to elaborate and provide copious examples of these questions; we all know what I’m talking about.) Indeed, it has been gratifying to see it become more mainstream for people to speak out about “crazy questions” and for popular opinion to begin to shift accordingly.
But I made a mistake.
No, this isn’t a retraction. My mistake was not in discouraging the invasive, superficial, nonsensical, ultimately vain questions that are still habitually resorted to, but in failing to provide an alternative. After all, even those who will readily acknowledge that the usual array of questions is inappropriate and unhelpful, if not worse, find it difficult to take the next step and figure out a better alternative. (The same goes for labels; people are increasingly willing to acknowledge that labels are a destructive force in the community, or at the very least misleading, but they lack the vocabulary, patience, and clarity to express themselves more precisely.)
I wish now to rectify this mistake, and have prepared a list of questions that I respectfully submit for the reader’s consideration. This is not meant to be an exhaustive and completely refined list, and in fact I hope that singles and those who act on their behalf will use these questions as a starting point for looking at themselves and others in a more meaningful and dignified way. As with all of Jewish life, one’s shidduch quest should be completely personalized within a general framework.
In addition, I wish to draw attention to the fact that, unlike the usual shidduch questions that will hopefully soon be obsolete, these questions are not meant to be answered in ten seconds or less; they are all entirely open-ended. Nor are there implicit “right” or “better” answers that the responder should strive to aspire to or conform to in order to improve his shidduch approval rating (though, of course, some answers could still be “wrong” in terms of objective Torah values).
Rather than try to peg human beings into narrow yet amorphous categories or grade someone’s responses to black and white questions, these questions are intended to discover the true essence and Jewish personality of the individual.
This list of questions is recommended for shadchanim, web sites, and singles themselves. It is not necessary for someone to respond in great detail to all of the questions, but the more one reveals about his true self (both to others and to his own self), the easier it will be to clarify what one truly wants and needs in a potential spouse. The usual sorts of shidduch questions encourage deception and a suppression of the true self.
These questions encourage deep honesty and careful introspection.
Finally, I don’t recommend that these questions to be asked on first dates or that they be presented in an interrogative style. Finding out about oneself and others should be a pleasant, gratifying experience, not something filled with discomfort and fear. Consequently, when two people are first meeting one another, it is more appropriate to establish a comfort level before asking deep personal questions such as these.
Here are the questions:
Tell me some things about yourself that you are most proud of. It could be personality traits, personal accomplishments, or specific things that you have done.
If you could go back in time and meet anyone, who are some people you would choose, and why?
How do you tend to go about things when you are in an environment in which you don’t know anyone (new shul, social event, etc.)?
What does it mean to you to be a Jew?
When you look back at your life at the end of 120 years, what would you like to have accomplished?
What would you like to accomplish in the next 5 years?
What misconception do people have about you?
If you had so much money that you never needed to work a day in your life, what would you do?
What would be the first thing you’d do after winning the Lottery?
How do you tend to resolve a difficult personal decision? Give appropriate examples if possible.