Peter Pearson

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.


Relevant Articles:

The Hidden Cost of Too Much Compromise in Your Relationship

Get the Most Out Of Couples Therapy


Peter Pearson, Ph.D., Relationship & Teamwork Expert for Entrepreneur Couples

Pete has been training and coaching couples to become a strong team since 1984 when he co-founded The Couples Institute with his psychologist wife, Ellyn Bader.

Their popular book, “Tell Me No Lies,” is about being honest with compassion and growing stronger as a couple.

Pete has been featured on over 50 radio and television programs including “The Today Show,” "Good Morning America,” and "CBS Early Morning News,” and quoted in major publications including “The New York Times,” “Oprah Magazine,” “Redbook,” “Cosmopolitan,” and “Business Insider.”

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  1. wow I love these questions for couples. I have been married for over a year now and I have been thinking of a way to bond with my husband. This will come in handy when we have our date night

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  4. Timo – thanks for the feedback and your willingness to experiment – ongoing experimenting is one way to keep relationships feeling alive

  5. Hi Bryan – The 20 questions exercise is designed to explore each other’s ideas in a (hopefully) safe way. This exercise is not designed to discuss past hurts and secrets —

    past hurts and secrets are good to discuss if they are thought to influence the relationship in its present form

  6. Elusiveness is something am disturbed about when having this kind of discussion with girlfriend. For me am open and wouldn’t mind talking about some past hurts and secrets but I find that each time I bring them, my girlfriend starts getting too tired or suddenly remembers that she has something to do.

    I find that very frustrating and I wonder if she is in the relationship for real. Though we are not married but I think if it comes to making a decision about that, I will always have second thoughts.

  7. Glad you appreciate the questions. Please think about them as guides to create your own questions for yourself or couples you work with. Obviously this is not an exhaustive list – I just want to get the conversational ball rolling for couples who have been or felt disconnected.

  8. Margot-
    Good question you ask and one I am sure you realize depends on the couple/context. Elusiveness is especially common when an affair is happening or when a partner has something to hide. It may also occur with someone who feels very insecure or unable to articulate their internal process and desires.
    Thanks for commenting.

  9. I like the list of 20 questions. Of course I’d make sure my clients will only be taking two or three of these to the dinner table, or the date would turn into an interview. The additional questions are a little out there for a normal everyday couple. I’m not sure if the dinner table at a restaurant would be the right place for these kind of questions, perhaps I’d save them for the bedroom talk. Over all very good ideas here. Thank you for getting the list together.

  10. I too am a family/ couples’ therapist, a consultant, a gerontologist, a professional mediator, an executive coach, a mother and a daughter. I always wear many different hats as do the two of you. I used to be able to ask these types of questions to my husband. i knew it was time to leave when he became elusive , rather than transparent in his responses.

    What do the two of you think about this type of response, frequently given by some spouses. I think it means they are frightened about digging deeper and with intimacy issues.

  11. Good questions! But I would always emphasise the importance to NOT go for sore spots, hidden/shameful secrets and old hurts… especially not, when you are on a dinner date;)

  12. 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!