Topics To Explore When Dating

People who date seriously often wonder what they should talk about at different stages of the courtship.  Even those with good conversational skills may be uncomfortable breaking the ice with someone new or wonder when to switch from light topics of discussion to ones that are more serious. Someone who feels comfortable discussing just about anything with someone new and does not seem to run out of topics to talk about as the weeks go by, may nevertheless overlook certain subjects that help them gain insight into the dating partner’s philosophy of life, goals for the future, and approach to different life situations.

The search for a marriage partner involves more than finding someone to love.  It is essentially a search for someone to build a spiritually satisfying and enduring life with. A dating couple should view their courtship as a time to connect to each other emotionally, have fun together, observe each other in different life situations and learn about each other’s significant life experiences, value systems, points of view and expectations.

How do you do all of this?  By balancing the enjoyable aspects of dating with making dates purposeful.  Before each date, think of a few things you would like to discover about the person you are dating or share about yourself, and introduce them into your conversation.  As time progresses, you will learn a great deal about each other. We have compiled a number of suggested topics and questions that can help the readers get past the initial awkwardness of their first few dates, begin to relate to each other, gain insight into each other’s personalities, and learn more about what makes their dating partner “tick.”

One of the ways to figure out what to discuss on a date is to understand what should take place during each stage of courtship. For example, a couple who is meeting for the first time needs to break the ice, get a general sense of what the other is like, and see if they have enough in common to be able to go on to a second date. The second date is an opportunity to see each other a little more clearly and decide if they would like to get to know each other better. The 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, this is not a time to reveal deep, dark secrets or highly personal information. There is also room for some lighter conversations that begin to show each person’s tastes, interests, and way of thinking.

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

  • Your family and educational background
  • What you are currently doing with your life
  • What made you choose your career/course of study/yeshivah/seminary/college
  • What you like about it/dislike about it
  • Where you see yourself in five years, and ten years, and how you hope to “get” there
  • The person you most admire and how they inspire you
  • What interests you and why you seem to be drawn to it
  • Your favorite hobby, why it appeals to you, how you follow it
  • Describe what you feel is the most satisfying achievement of your life thus far.
  • An interesting sefer or article you have read and your reaction to it, even if the topic is controversial
  • The most interesting experience you ever had at work or yeshivah

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 that your date can talk about the same topic. Do not 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 is perfectly fine to get off track during the conversation because 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 your original topic later.
Helpful Topics To Help You Get To Know Each Other Better
By the third date, you may feel a little more comfortable with each other and will find it somewhat easier to talk to each other. During the next stage of dating, certain questions and subjects 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 to consider over the next several dates:

  • What you would like your future home to look like – Everyday, Shabbat, Chagim etc.
  • The experiences that had a positive affect on you and how they affected you
  • An experience that influenced you to make a change in your life or a decision about the future
  • Your feelings about Eretz Yisrael versus their feelings about where you now live
  • What you think is your greatest strength and greatest weakness
  • What you feel you really need to work on in order to reach your full potential
  • The role Torah and Yahadut plays in your life
  • Your tastes in food, clothing, or music
  • How you get along with different personality types
  • The things that make you happy or sad
  • How you handle frustration
  • Something that fascinates or excites you
  • If you spent time learning in Eretz Yisrael, talk about the experience and how it affected you
  • How you handle challenges
  • How you define a true friend