Play “Twenty Questions” With Your Partner

Peter Pearson, Ph.D

Do you remember the game “Twenty Questions?” You could ask twenty questions to identify what thing the other person was thinking about.

Here’s a variation on that, for your next dinner date or when you have some spare time. Using the questions below, you can find out a little more about your partner and vice versa. These questions will help you go a little deeper than discussing work, kids, vacations, or sports.

Interestingly these are the kinds of questions couples often ask each other in the early stage of a relationship. But as time hurtles forward, these great questions get neglected and then abandoned.

For an interesting and stimulating conversation, try these questions to discover or rediscover who your partner is.

(If you’re having trouble even getting a conversation going with your partner,
click here for help
.)

The one quality to keep in mind for the questions below is to treat the responses with respect. Try not to argue or negatively judge any of the responses. Be like a compassionate reporter who is writing an interesting story.

Here is what you can ask your partner (or that your partner can ask you) – you can even test how you each think the other would answer the question first:

1. If you could change only one thing in your life, what would that be and why?

2. In a regular day, what do you find yourself thinking about the most?

3. If you could write a song about your life, what type of music would you use?

4. What things in your life bring you the greatest pleasure?

5. What do you feel is your greatest accomplishment in your life? Did other people help to make that happen?

6. In what settings are you the happiest / eager / most comfortable?

7. What things do you look forward to each day? In your life?

8. If you had three wishes that would come true, what would they be?

9. What other things would you want to change now, and why?

10. What major regret do you have so far in your life? Is it too late to change it?

11. What would be my ideal romantic date?

12. Is there a belief or attitude that seems to interfere with creating or pursuing a big dream?

13. What are a couple of things that you appreciate about our relationship and why do these things seem significant?

14. In what situations do you feel most afraid or insecure?

15. What would you like to do outdoors that you have not done before? Are there any extreme sports that you’d like to try?

16. What country would you like to visit that you haven’t visited yet?

17. What family member did you most admire when you were a child?

18. What activities did your mother/father do that you most wish he’d taught you?

19. What do you most wish you’d learned from your mother/father?

20. Name 3 things that most excite your imagination when you imagine doing them?

21. What question about our money or future spending do you find hard to ask?

22. What are your favorite things to spend money on?

23. Who are you most envious of?

 

For the brave ones of you, enter your name and email address here to see 10 more questions that get a little more personal, and to find a printable version of all the questions:

I think it is hard to love someone or something if you don’t have some emotional understanding or feel for it. You also can’t love something you didn’t know existed.

I hope you find this voyage of discovery satisfying.

Keep stretching and growing,

Peter Pearson

(Note, you can opt in above for a printable version of these, bookmark this page on your computer or smartphone, or even email these to yourself here.)

P.S. Do you have a question to add to the list? Please note it in the comment section below.

Category: Communication,Couples' Blog
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  1. These are excellent questions for both newly dating partners and couples who have been together for years. I will share these with the couples I see for therapy. Thank you!

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