Fresh Questions to Fill Up the Dead Space

Feb 19, 2010

I’ve been told there is one important rule for keeping date-night conversation fresh:

Avoid talking about your children or your job.

Hmm. Not easily done. The first time resulted in lots of eye-shifting, salad-fork-fidgeting and empty dead space. These are default go-to topics; we resort to our kids and our careers when we can’t come up with anything else to say. The problem is we seldom get to know one another beyond the same well-worn conversation paths. In no time date night or time with friends feels like watching the same sitcom rerun for the hundredth time. Everyone is telling the same stories. Again and again and again.

“Then what in the world are we supposed to talk about?!?!?!”

I’m glad you asked. Here’s a list of open-ended questions that do not fall under the over-used, oft-abused topics. Keep these kinds of questions close the next time you want to connect with your spouse, a friend or even your children. Sometimes all it takes is ONE of these questions to fill a dead night with fresh life. And you’ll be surprised how much you ending up learning about this person you thought you already knew:

  1. If you could take a vacation anywhere in the world, where would you want to go? Why?
  2. What’s one thing you’ve always wanted to do but never done?
  3. If you could pick a different first name, what would it be?
  4. Spring, Summer, Autumn or Winter? Why?
  5. If your house was burning down and you could only grab one thing, what would you grab?
  6. What do you believe is your greatest personality trait? Why?
  7. What do you believe is your greatest physical trait? Why?
  8. What’s the one thing you wish you could change about yourself?
  9. When you were in high school, what did you do on an typical Friday night?
  10. Tell me about your favorite musicians. What kind of music do you gravitate to if you’re having a rough day? What kind of music gives you energy?
  11. Name one of your personal heroes, living or deceased, and then tell my what you admire about him or her.
  12. What book has had the greatest impact on your life?
  13. If you could do any sport in the Olympics, which one would you choose?
  14. If money wasn’t an issue, where would you live (country, state, city)?
  15. What is your dream car (NOTE: I could care less about cars, but this one is a winner with the guys)?
  16. Tell me about one of your best childhood memories.
  17. If you could rewrite your childhood, what would it look like?
  18. If you could remodel one room in your house, which room would you choose and what would you do to it?
  19. Who is the most generous person you know?
  20. Who has been the most influential person in every decade of your life?

Anything to add?

P.S. Next week I’ll reveal one of my secrets for sparking conversation with the kids!


  1. Tonya

    Great questions, Michele. Both Chuck and I are depth challenged. 🙂 So we bring our questions with us to dinner. But what I find is normally after two or three questions the conversation naturally flows. You are right that is very hard to not default to the kids or careers. Building intimacy takes time, but the dividends pay wonderfully.

    • Michele Cushatt

      So true, Tonya. I've been doing this with a couple friends lately, bringing one or two fresh questions to our time together. I've been surprised at how much I'm learning about long-time friends!


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