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Dating Advice #164 - Pinpoint Questions
Dating Advice 164

Dating Advice #164 - Pinpoint Questions

Drawing out crucial information at all three stages of the dating process.


Dear Rosie & Sherry,

I'm hoping you can give me some of your on-target advice. I'm successful in business and a good conversationalist. When I'm on a date, looking for the right woman to marry, I know that I should be probing for insights into her philosophy of life, goals for the future, and approach to different life situations.

Now for my problem: I want someone I can build a life with, but I'm uncomfortable asking such questions straight out. Can you give me guidelines for how to direct the conversation in a way that I will get the information I need?


Dear Stan,

You are correct that obtaining this information is crucial to any serious dating process.

One of the ways to figure out the types of questions to ask is to understand what should be taking place during each stage of courtship. For example, two people who are meeting for the first time need to break the ice and find out enough about each other to see if they are somewhat comfortable in each other's presence and have enough in common to go on a second date.

The second date is an opportunity to see each other a little more clearly and decide if they would like to begin to get to know each other better. Conversation during this "meeting each other" stage of dating usually consists of "airplane talk" -- the kind of discussions people may have with a stranger they sit next to on an airplane and may never see again; in other words, no deep dark secrets or very revealing information. There is also room for some lighter conversations that begin to show personal tastes, interests and way of thinking.

Good topics and questions for the earliest stage of dating include:

  • Jewish "geography".
  • Your family and educational background.
  • What you are currently doing with your life.
  • What made you choose your career/course of study.
  • What you like/dislike about it.
  • What you like to do for "fun," and why that is enjoyable for you.
  • The person you most admire and how he/she inspires you.
  • What interests you, and why you are drawn to it.
  • Your favorite hobby, why it appeals to you, how you follow it.
  • Describing the most satisfying achievement of your life.
  • Is there something you have dreamed of doing for a long time? Do you think you will ever be able to do it?
  • An interesting article you've read and your reaction to it, even if the topic is controversial.
  • The best vacation you ever took and why it was so great.
  • The most interesting experience you ever had at work or school.

Some people find it easier to mentally review the content of their conversations before they go out. You can see if dating is easier when you take some pre-date time to think through certain ideas and how you will present them.

If you find yourself monopolizing the conversation, stop yourself and start asking questions so your date can talk about the same topic. Don't be afraid to get off on a tangent, or to ask questions such as, "How did that make you feel?" "What was it like?" "What did it look like?"

It's okay if the conversation gets off track when one of you makes a comment that reminds the other of a story or something you want to share. Let the conversation flow - you can come back to the original topic later.


By the third date, you probably feel a little more comfortable with each other and will find it somewhat easier to talk. During this stage of dating, certain conversation will help you learn more about each other's personalities, experiences, philosophy of life, interests, opinions, reactions to different situations, and ways of thinking. Here are some topics and questions you can gradually introduce over the next several dates:

  • What it was like growing up in your hometown/in your family.
  • An experience that influenced you to make a change in your life or a decision about the future.
  • What you think is your greatest strength, and greatest weakness.
  • Where you see yourself in five years, and ten years, and how you hope to "get there.".
  • What you feel you really need to work on before you can achieve your full potential.
  • How you like being Jewish.
  • Your feelings about Israel versus feelings about where you now live.
  • If you have spent time in Israel, what that experience was like and how it affected you.
  • The experience or thought process that led to your level of religious observance.
  • Your tastes in food, clothing, furniture, art and music.
  • How you get along with different personality types.
  • Things that get you angry or depressed.
  • Something that fascinates or excites you.

After you have gone out enough times to believe that the two of you have the possibility of marriage, we strongly recommend that you bring up the subject of marriage to make sure that you are both dating for the same purpose. Why risk a dead end? You can express your interest in marriage without putting either of you on the spot: "I enjoy going out with you and I would like to get to know you better. But, I'd like you to know that I am dating because I hope to find the person I will marry. It's far too early for us to know if we are right for each other, but I would like to know if we share that. Are you also looking for a marriage partner?"


When you both believe things are moving in the direction of marriage, you are ready to be even more open about your feelings. The topics listed below allow you to touch upon some very personal emotions, and also give you an opportunity to discuss how you envision married life. Your discussions can include:

  • More details about your family, including the different personalities of family members, and the differences between your respective families.

  • A description of how you envision Shabbat and holidays in your home. Try talking about things that impressed you in your house growing up, or in the different homes you've visited for Shabbat.

  • Your friendships - what your closest friends are like, how those friendships developed, experiences you have shared, what you value in those friendships.

  • A challenge you have dealt with, why it was difficult for you to face, and how you dealt with it.

  • A moral dilemma you have faced, why it was difficult for you to resolve, and how you resolved it.

  • Your belief in God, and how you have felt His involvement/guidance in your own life.

  • The role that doing acts of kindness plays in your life, and the role you would like it to play in the future.

  • How you would like to raise your children.

  • How you deal with time pressure (such as too many tasks to complete in too short a time).

  • The potential you believe you have, how you hope to utilize it, and how honest you are about evaluating your potential.

  • Your expectations about the standard of living you would like to have when you are married, your sources of income, and your attitudes about spending and saving money, following a budget, and giving to charity.

  • The manner in which you would like to share household responsibilities, including child care.

  • The role of Torah study, and how much time you envision devoting to study each week.

We hope these suggestions have been helpful. You can adapt them to your own situation, to pinpoint whether the one you are dating is truly the one for you to marry.

All the best,

Rosie & Sherry

September 18, 2004

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The opinions expressed in the comment section are the personal views of the commenters. Comments are moderated, so please keep it civil.

Visitor Comments: 6

(6) Anonymous, October 20, 2013 1:13 AM

Thank you!

Very, very, useful info, presented in a clear matter. Thank you!

(5) Baruch, February 25, 2011 3:22 PM

Thank you

I've heard over and over again how important it is to ask the right questions without ever getting a good idea about what those questions might be (with a few exceptions). Thanks so much for this list, and for giving me an order of operations.

(4) Z, January 29, 2010 1:45 AM

on my way

To better dates. Thank you so much for this great set of guidelines.

(3) Zev, August 24, 2006 12:00 AM

Priceless article

Man was I lost before reading this! I think I was doing much of stage 3 on the first date (no I'm not exaggerating). I'm sure it made me look really desperate and clueless. These guidelines look like a great roadmap, showing when to take things up a notch and when to slow things down. Btw, I was surprised "tastes in food, clothing, furniture, art and music" was in stage 2...seems like first date material to me but what do I know. Thanks!

(2) Anonymous, November 6, 2004 12:00 AM

Very nice and clear!

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