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 for these questions to be asked on first dates or for them to 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.
Without further ado, 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, 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?
If you hit the Lottery tomorrow, what would be the first thing you did?
How do you tend to resolve a difficult personal decision? Give appropriate examples if possible.
How do you feel about taking risks?
How do you like to spend Shabbos?
How do you like to spend your vacations?
What would it take to make you happy in life?
How have you grown or changed in the past 5 years or 10 years?
How would you like to grow or change in the next 5 years or 10 years?
What are some of the challenges you've had to face in life, and how did you deal with them?
What You're Looking For
What does marriage and having a spouse mean to you?
What do you hope / expect a spouse to bring to your life?
What do you hope / expect to bring to a spouse's life?
What are some of the first things you look for in a potential spouse?
Describe some aspects about people that you are specifically not looking for in a spouse.
In what ways would you like a potential spouse to be similar to you? In what ways would you prefer for (or at least accept) a potential spouse to be somewhat different than yourself? (For example, a shy person by nature might be more comfortable with a similarly shy person, or he might prefer a more outgoing person to be more outgoing on his behalf and/or help him become more outgoing.)
In what ways are you willing to compromise / be flexible to give a shidduch a fighting chance? In what ways are you unwilling to compromise / be flexible?
There you have it. Once again, I encourage everyone to compare these questions to the status quo and to decide strictly in terms of merit. Those people whose identity and essence consist of nothing more than the type of Yarmulka they wear and the Yeshiva they associate with are welcome to stick with the status quo, and have my sincere condolences. If they relate to others in a superficial way, they should not complain when others relate to them in a superficial way.
On the other hand, those people who can't be defined by religious buzzwords or understood at a first glance, who in fact refuse to be reduced to trivialities, will hopefully learn to relate to others in a more qualitative and meaningful fashion.
Anyone who wishes to receive a copy of these questions by e-mail or submit their own is invited to contact me.