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Do you remember the game “Twenty Questions?” You could ask twenty questions to identify what animal,
vegetable or mineral the other person was thinking about. Here’s a variation for your next dinner date to find out
a little more about your partner and vice versa.

The following questions will help you go a little deeper than discussing work, kids, vacations, or sports.  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 again to discover or rediscover who your partner is. Print them out and bring
them to dinner.  The one quality to keep in mind is to treat the responses with respect. Please don’t argue or
negatively judge any of the responses. Be like a compassionate reporter who is writing an interesting story.

  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. On your drive to/from work, what consumes your mind, the majority of the time?
  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/saddest/unsure/afraid?
  7. What do you look forward to each day?
  8. What do you look forward to in your life?
  9. If you had three wishes that would come true, what would they be?
  10. What other things would you want to change now, and why?
  11. What major regret do you have so far in your life? Is it too late to change it?
  12. When you reach old age, what do you think you would wish you had done? (that you haven’t attempted so far)
  13. Is there a belief or attitude that seems to interfere with creating or pursuing a big dream?
  14. What are a couple of things that you appreciate about our relationship and why are these things significant for you?
  15. Who was your best friend in primary school – and why?
  16. Who was your best friend in high school – and why?
  17. Of all the people you have known, read about, or fantasized about, who is your biggest hero – and why?
  18. Of all the people you have known, read about, or fantasized about, who is your biggest villain – and why?
  19. If you had enough money and never had to work again in order to survive, what would you spend your life on?  Why?
  20. What do you still need to do or be in order not to write ‘if only...’ on your gravestone?

Just do one question during each date.  Choose the question together beforehand, and prepare yourself to tell
your partner about your thoughts on the subject for about 20 minutes uninterrupted.  Make notes and feel free
to let your thoughts travel wherever they may from the question.  Make your story about you, not 'us', so that
your partner gets the opportunity to see you as an individual rather than merely a part of his/her life.  Take turns
to start, so that on one date you'll start, and your partner will finish, the next date your partner will start and you
will finish

Treat your partner's responses with respect, listen actively (if you don't know how to do this, go look at the
Communication Skills), don’t argue, offer your opinions, negatively judge or take personally his/her
responses, try to hear your what your partner is saying about him/her. Be like a deeply interested and
compassionate reporter who is interviewing someone for an important story.  You can take notes while your
partner is speaking, but don't interrupt.  When your partner has finished his/her story, you must summarise the
story in your own words so your partner knows that you have not only heard, but also understood, what s/he was
saying.  Only when you have had confirmation that you have correctly understood the story is it your time to tell
your story.
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JMDpsych: Twenty Questions