Shidduch date questions prepared by Miriam Zeitlin

Great Shidduch Date Questions to Keep Conversation Flowing

Dating is all about getting to know the other person. But, unless you’re a natural conversationalist, finding shidduch date questions and topics to talk about that can be tough, (especially if you’re already feeling under pressure). 

Using her experience as a frum dating coach, Miriam Zeitlin shares top questions to ask on a shidduch date that can help you learn about the person you are dating on a deeper level.

16 Ice Breaker Questions to Ask on a Shidduch Date

  1. Who is the most fascinating person you’ve met?
  2. What are some accomplishments you are proud of?
  3. What would you do if you had enough money to never have to work?
  4. What does your perfect vacation look like?
  5. Among your friends, what are you best known for?
  6. What fad did you never really understand?
  7. What do you do to unwind?
  8. Name a fear that you have?
  9. What wrong assumptions do people make about you?
  10. Do you prefer to work alone or in a team?
  11. How have you changed since high school?
  12. Before you make a call, do you rehearse what you will say?
  13. What are you most grateful for?
  14. What would you do with extra time if you never had to sleep?
  15. What have some of the happiest moments in your life been so far?
  16. What is the most spontaneous thing you ever did?

Shidduch Dating Conversation Topics

If the person you’re dating isn’t much of a talker, you may need to work a little harder to strike substantial shidduch date conversations. Remember that it might take time to establish enough of a relationship to converse naturally.

Here are some ideas for general shidduch conversation starters:

  • The most interesting experience you ever had…
  • Let’s play Jewish geography!
  • If you did a PhD what would the topic be…
  • In your wildest dreams, you’d love to…
  • The best book you ever read…
  • An article that really got to you and why…
  • If you were stranded on a desert island and could only take 3 things…
  • The best restaurant you’ve been to…
  • A summer experience…
  • How’d you choose your career/course?
  • Your best birthday celebration…

Shidduch Date Questions, Date by Date

If you’ve already been out a couple of times and are looking for shidduch date questions that will help you gain a better understanding of the other’s thoughts and feelings, you may want to try some of these suggestions:

Dates Three – Five:

  1. What energizes you?
  2. What makes you angry?
  3. What or who has made the biggest impact on you in life?
  4. What inspires you?
  5. What’s you’re greatest strength (and greatest weakness)?
  6. Where do you stand politically?

Dates Six and On:

  1. What qualities in a future spouse are most important to you?
  2. What personality types do you best compliment?
  3. Have you visited Israel? How did it affect you?
  4. Describe your taste in decor, clothes, food, and music
  5. What would you love to learn more about?
  6. What life accomplishment made you most proud?

Hashkafic Shidduch Topics

While you now have questions to ask on a first shidduch date and what to talk about on a second shidduch date, the conversation doesn’t stop there!

For future dates, you can dive deeper and ask about:

  • Friendships and how they were formed and developed
  • Family, who they’re close with, and the home dynamics
  • Future children bezH, and how you’d want to raise them
  • How Chessed features in their life
  • How do they picture their home responsibilities being met
  • How much Torah learning plays a role in their life
  • Life values and priorities, in general
  • How you’d imagine Shabbos and Yomtov in your future home
  • How you’ve faced life’s bumpy roads and challenges and learnt from them
  • How you resolved moral dilemmas and fueds
  • Emunah and Bitachon and how they feature in the day-to-day
  • One’s absolute red lines
  • How you relate to each other
  • Finances and attitudes towards money
  • Level of religious observance
  • What they like to emulate from your parent’s marriage (or avoid)
  • How would they handle spousal stresses and arguments?
  • Technology in the home
  • Community Importance

There’s More to Shidduchim Than Just Shidduch Date Questions 

If you find the conversation flowing, you may need no more advice on what to talk about on a shidduch date. But for many, some pre-prepared conversation starters can go a long way.

If you’re looking to feel ready for each date and equipped with confidence that shines, contact Miriam Zeitlin and meet a dating coach focused on your success!

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