Excerpted from Rebbetzin Tziporah Heller’s Question and Answer series on Naaleh.com
Can you give me some guidelines on questions I should ask singles before I try to set them up?
You should try to obtain as much information as you can about their background, nature, and goals. The more you get them to talk, the more you’ll find out about them. The way they speak about their siblings, family, and life in general will tell you a lot about who they are. Are they effusive or reticent? Are they positive or negative? How do they feel about themselves? Do they hold their Rabbi in regard or do they tend to put him down? Asking a lot of background questions will give you a sense of what the person will have in common with a prospective mate. Inquiring about their goals and what they really want in life tells you who they really are and what their values are. It is also important to find out their hashkafic views and their level of religious observance. Ask about their economic background and what standard of living they will expect, so you can look for compatibility. It is your responsibility to find out if there are any physical or mental problems. You can then set them up with someone who is likely to be accepting of it.
There is a lot of “trophyism” in shidduchim. People are obsessed with inane issues such as “What will everyone say? Is he the best boy in Yeshiva? Is he at the top of his profession? Is her family wealthy? Does she look right?” Answers to these questions don’t really tell you who the person is, where they are coming from, and where they plan on going, whichare the things that will make or break a marriage.