How do you feel about taking risks?

How do you like to spend Shabbos?

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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 or 10 years?

How would you like to grow or change in the next 5 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 yarmulke they wear and the yeshiva they associate with are welcome to stick with the status quo. They 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.

Chananya Weissman is the founder of EndTheMadness (www.endthemadness.org). His collection of original divrei Torah, “Sefer Keser Chananya,” can be obtained by contacting him at [email protected].


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Rabbi Chananya Weissman is the founder of EndTheMadness and the author of seven books, including "Tovim Ha-Shenayim: A Study of the Role and Nature of Man and Woman." Many of his writings are available at www.chananyaweissman.com. He is also the director and producer of a documentary on the shidduch world, "Single Jewish Male." He can be contacted at [email protected].