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 the Twenty Questions game, 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.


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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A Glossary of Terms that are sometimes Confusing

Couples Therapy is a counseling procedure that seeks to improve the adjustment of two people who have created an interdependent relationship. There are no standard procedures to help two people improve their adjustments to each other. Generally, a more experienced therapist will offer more perspectives and tools to a couple. Length of treatment will depend on severity of problems, motivation and skills of the therapist. A couple can be dating, living together, married or separating and may be gay, lesbian or heterosexual.

Marriage Therapy is a term often used interchangeably with marriage counseling. The term marriage implies two people have created a union sanctioned by a government or religious institution. The methods used in marriage counseling, marriage therapy and couples therapy are interchangeable and depend more on the specific challenges of each unique couple.

Psychotherapy is one or more processes to help improve psychological and emotional functioning. Examples are psychoanalysis, cognitive therapy, behavior therapy, Gestalt therapy, Transactional Analysis, Rational-Emotive therapy, or group therapy. Many forms of psychotherapy are blends of different approaches. For example, newer forms of psychotherapy called energy psychology draw upon recent advances in brain and neuroscience. These approaches often build on cognitive behavioral methods.

Clinical Psychologist. After graduating from college, it usually takes about five years of graduate school to get a Ph.D. in Psycholgy. It then requires an additional two years of supervision and passing a written (and often) an oral exam. There are a few states that allow psychologists to prescribe medications (with additional training) but that is uncommon.

Psychiatrist. After graduation from medical school, there is a generally a 4-year psychiatric residency. After the completion of this training, psychiatrists must pass an exam issued by the American Board of Psychiatry and Neurology to obtain certification and legally practice in the field. Psychiatrists can prescribe medications.

Clinical Social Worker. This profession usually requires two years of study after obtaining an undergraduate degree. While specific licensure requirements vary by state, most require clinical social workers to obtain 3,000 hours or 2 years of supervised clinical experience, after obtaining a Masters degree. Social workers can also specialize in diverse fields such as human services management, social welfare analysis, community organizing, social and community development, and social and political research.

Marriage and Family Therapist. Obtaining this license requires a Masters degree which takes approximately two years of post graduate study. The license also requires 3000 hours of supervised work and passing written exams.

The Couples Institute. We have assembled a group of top notch therapists at The Couples Institute. Whatever marriage help or marriage advice you are looking for, we are here to serve you. While most other therapists see only a few couples a week, we specialize in marriage and couples relationships, working to develop and bring you the most current and effective approaches to couples therapy. For more information about couples therapy or marriage counseling, see our couples therapy section.