How to have a great conversation

with anyone

Prerequisites: listening and listening to listening

 

It's easier and more predictable than you imagine: the cycling technique

Using this "cycling technique" almost always guarantees an engaging conversation that will leave both of you wanting more and feeling great about each other.

Ambience is important

Without some dedicated time set aside, in a relatively comfortable environment, with low ambient noise, the chances for a good conversation are compromised. Set up the circumstances in advance. You could even use the cycling technique over the telephone or with video chat.

Yes, the cycling technique is different

And you may need to choose courage to take the initiative to get it started with your conversation partner. See undoing fear and courage.

Start the conversation like this:

"Recently I heard about an idea of how two people could get to know each. I think it would be fun to try it out with you. May I tell you about it?" 

...

"It works like this. One of us starts first and asks the other person a personal question. In general, the question should be open-ended...not one that could be answered with a 'yes' or 'no.' 

"After the question is answered, then the person asking the question also answers their own question.

"Then it's the other person's turn to do the same.

"If, by chance, one of us doesn't want to answer a given question, we can say, "pass" and the other person comes up with a new personal question.

"How do you feel about this idea? Could we try it out? Would you like to go first? Or me?"

...

Some extra points

You might want to go first to help break the ice and to give the other person some idea of what "personal question" means.

Some questions I like to start out with are:

  • "Name at least three things you like about yourself."

  • "What do you dislike about yourself?"

  • "If you could go back and give advice to your ten-year-old self, what would you say?"

  • "If you had kids, how would you raise them differently than the way you were raised?"

Although the cycling technique works best with two people, it could be used with three (or a few more) in round-robin fashion, with each person answering every personal question posed. 

When answering a question, choose courage to be as open (and vulnerable) as possible.

Questions to ask

There are some good questions at 37-questions

Below is an extensive list (you'll never run out!) of juicy personal questions. 

You could bring a list with you...or just review these lists before hand so you won't have any trouble coming up with at least ten questions for you to ask.

The questions

Level 1 (less personal)

 

  • What do you like about yourself?

  • What do you dislike about yourself?

  • What would you like me or others to most appreciate about you?

  • What type of compliment touches your heart most?

  • What most annoys you about other people's behavior?

  • Which particular behaviors of other people are most difficult for you to understand?

  • What are the things that you consider to be "essential" in your life that the average person probably doesn't consider to be essential?

  • If you had all the time and the money in the world, what would you spend your time doing?

  • What makes you happy or gives you the deepest sense of fulfillment?

  • If you knew that whatever you requested would be granted, what would you ask for and who would ask it of?

  • If you could go back and give advice to your ten-year-old self, what would you say to them?

  • How would you raise your own child differently than the way you were raised?

  • What do you say are the most significant differences between men and women?

  • What behaviors of the opposite sex are most difficult to understand or annoying to you?

  • Are you amazed at how well the world works? Or are you surprised that it doesn't work better than it does?  Elaborate.

  • What is the one thing that you have learned in your life that has made the biggest difference in the quality of your current life?

  • If you were limited to giving three pieces of advice about "living well" to another person and you knew they would take your advice to heart, what would those three suggestions be?

  • What other virtue or character trait, besides courage, do you consider the most important in living a fully self-expressed and successful, life?

  • What, for you, is the most important, most empowering question that you can consistently ask yourself?

  • [To a woman] What are the specific behaviors make you feel safe, adored, and cherished by a man?

  • [To a man] What are the specific behaviors make you feel powerful, admired, and respected by a woman?

  • If you wanted the rest of your life (starting from today) to a major shift from you past life, what decisions and actions would you take immediately?

  • [To a woman] What particular pleasures and advantages to you appreciate about being a woman?

  • [To a man] What particular pleasures and advantages to you appreciate about being a man?

  • [To a woman] What particulars pains and disadvantages do you dislike about being a woman?

  • [To a man] What particulars pains and disadvantages do you dislike about being a man?

  • [To a woman] What do you like and/or appreciate about men?

  • [To a man] What do you like and/or appreciate about women?

  • [To a woman] What do you dislike and/or find annoying about men?

  • [To a man] What do you dislike and/or find annoying about women?

  • Tell me about a time that something really bad happened, but later you discovered it to be a gift.

  • How would your life be different today if you totally loved and respected yourself?

  • If you REALLY believed that the world was put here JUST as YOUR playground and everyone on the planet was here as YOUR playmate or potential playmate, how would you act differently from this moment on?

  • Please share with me in what ways you find yourself to be a victim of yourself, of others, or of reality?

  • [To a woman] In what values do you think it is possible to get from a man that are impossible for you to get from a woman?

  • [To a man] In what values do you think it is possible to get from a woman that are impossible for you to get from a man?

  • What particular character traits uniquely define you?

  • What is your favorite movie?  Why?

  • If you could play God and change one fundamental thing about the Universe or human behavior, what would that change be?

  • What part of your life do you find to be the most challenging for choosing courage?

  • What are your thoughts, feelings and actions whether you pass a beggar on the sidewalk?

  • What part of your life are you the happiest with and why?

  • Are you more attracted to sensible people or to imaginative people? Say more about that.

  • Are you more serious and determined or more easy-going? Say more about that.

  • Do you apply the same rules regarding sexual expression to men and to women?  If not, what differences are there in the rules that you apply?

  • If you had 25 hours in the day, how would you use that extra hour?

  • If you had 36 hours in the day, how would you use those extra 12 hours?

  • If, as the president of the U.S. for one day, you could make one decision that would continue to be in effective indefinitely, what would that be?

  • If, as the president of the China for one day, you could make one decision that would continue to be in effective indefinitely, what would that be?

  • If, as the president of a major university for one day, you could make one decision that would continue to be in effective indefinitely, what would that be?

  • If, as the chief of police for one day, you could make one decision that would continue to be in effective indefinitely, what would that be?

  • What complaints does your mother have about your father?

  • What does your mother like about your father?

  • What complaints does your father have about your mother?

  • What does your father like about your mother?

  • What difficulties/challenges have your parents have had to deal with in being married?

  • What complaints has your mother have about you?

  • What does your mother like about you?

  • What complaints has your father have about you?

  • What does your father like about you?

  • What are the complaints have you had about your mother?

  • What do you especially appreciate about your mother?

  • What are the complaints have you had about your father?

  • What do you especially appreciate about your father?

  • If you saw life as a movie, where everyone that you encounter, whether your parents or a stranger on the street, is seen as a magnificent actor/actress playing an incredible role in this movie (as your parent or as a stranger or …), how might you experience and live your life differently than you do now.

  • If you were born into the position of being king/queen of England, how would you use your publicity power different than others who were king/queen of England have done?

  • Imagine you were given eight days in a week. And this extra day would be completely empty to start with; you could fill it any way you wanted to. How would you fill it differently than the other days that you have already filled?

  • If somehow you KNEW (without any evidence that you could show to others) that a specific jet plane that was scheduled for take-off from Los Angeles International Airport ten days from now would crash and kill all 206 passengers aboard. But, if you could somehow stop that plane from taking off as scheduled, then the people would be saved. What would you do, if anything, to try to stop that plane from taking off as scheduled?

  • Usually we think only other people are superstitious. Can you identify any superstitious behaviors or beliefs that you have?

  • Imagine you were automatically paid a “living stipend” each month so that you had no “need” to work as long as you received this stipend. Also imagine that the only “requirement” to continue to receive this stipend was to spend a minimum of six hours a day, five days a week doing whatever you thought would most contribute to and impact humanity. What would you do during that thirty hours per week?

  • When was the last time you felt you were treated unfairly?  Tell me about that.

  • When was the last time you felt you treated another unfairly?  Tell me about that.

  • In what ways do you think life has treated you unfairly? 

  • Have you had any transcendent spiritual experiences?  If so, tell me about one.

  • If money and time were no issue in your life, what would be your next problem?

  • If you had to choose between just enough money and total free time and no free time, but as much money as you can possibly use, which would you choose and why?

  • On the phone, do you just assume everything will be said - or do you rehearse what will be said? Say more about that.

  • Given what you know today, what new or different choice would you have made in your life five years ago?  Why?

  • Given what you know today, what new or different choice would you have made in your life ten years ago?  Why?

  • Given what you know today, what new or different choice would you have made in your life when you were five years old?  Why?

  • Given what you know today, what new or different choice would you have made in your life when you were ten years old?  Why?

  • Given what you know today, what new or different choice would you have made in your life when you were fifteen years old?  Why?

  • Given what you know today, what new or different choice would you have made in your life when you were twenty years old?  Why?

  • Given what you know today, what new or different choice would you have made in your life when you were twenty-five years old?  Why?

  • How safe do friends and family feel to tell you anything, even their deepest secrets? Why do you think that is?

  • How would you want your funeral to be conducted? What do you want people at your funeral to say about you?

 

Level 2 (more personal)

 

  • [To a man] If you could be a woman, what benefits of being a woman would you be interested in taking advantage of?

  • [To a woman] If you could be a man, what benefits of being a man would you be interested in taking advantage of?

  • What memory, if any, would you erase from your mind if you could?

  • What or who would you die for?  Under what circumstances would you choose you own death?  Why?

  • What does your mother least understand about you?  Your father?

  • What do you least understand about your mother?  Your father?

  • Where you spanked or otherwise hit or abused as a child? Please elaborate.

  • What is the most important thing that I could know about you that I currently don't know or don't understand about you?

  • What about me or my behavior is confusing for you or that you don’t understand?

  • If you could completely ignore culture, tradition and what others expected of you, describe how you would you act and live your life differently?  If others would applaud and approve of ANYTHING that you did (or didn't do), what would you do (or stop doing)?

  • What is the craziest thing you've ever done in your life?

  • What is the stupidest thing you've ever done in your life?

  • Tell me about a time in your life when you lied big.

  • Tell me about a time in your life when you stupidly told the truth.

  • Tell me about a time in your life when you chose the most courage.

  • Tell me about a time in your life when you were really scared, and you didn’t choose courage.

  • Tell me about the time when you were most embarrassed.

  • What are the advantages of a romantic relationship with a younger man/woman?

  • What are the advantages of a romantic relationship with an older man/woman?

  • Do you view marriage and divorce as equally viable for fulfilling life, to be judged for the particular circumstances of a given couple? If yes, why? If no, why not?

  • Which man/woman would you most like to live with for the next six months?  Why?

  • If you had to make a choice between your spouse/lover having a sexual affair with no emotional/intimacy component OR to be emotionally/intimately involved with another person without any sexual expression, which would you choose and why?

  • Tell me about a time you were really drunk.

  • Tell me about a time you were really naughty or broke some big rules.

  • Tell me about the most romantic experience of your life.

  • How many great loves have you had in your life? How many great loves would you like to have in the rest of your life?

  • What has been the biggest guilt of your life?

  • What actions (or non-actions) are you currently taking in your life that you feel guilty about?

  • What actions would you like to take in your life that, if you did, you would feel guilty about?

  • What benefits can you find for feeling guilty?

  • What feelings do you have with me that you like?

  • What feelings do you have with me that you dislike?

  • Do you think that the exchange sexual favors for money (prostitution) should be illegal or legal? Explain the justifications for your position. If you oppose legal prostitution in general, would you oppose legal prostitution for the disabled, who are often not able to easily find sexual expression otherwise? Why?

 

Level 3 (most personal)

 

  • Share with me something you don’t want me to know.

  • What about you is most hidden from others in your life?  What is most frightening to reveal to others?

  • Were you sexually abused or molested as a child, either by a relative or non-relative? Describe more fully.

  • What would you be most frightened of sharing with your parents?

  • What would you be most frightened of sharing with your boyfriend/girlfriend?

  • What would be the most frightening or embarrassing thing to share with me right now?

  • What are you avoiding looking at or doing in your life right now?

  • What is the most insensitive or cruelest thing you've done in your life?

  • What is the biggest regret of your life?

  • If you could get away cleanly (both legally and emotionally) with killing one person in the world, and you were compelled to kill someone (other than yourself), whom would you choose?

  • Imagine that another you was instantly created and sitting beside you right now. But they think that are you just as much you as you think you are you. From your perspective, they are a copy of you. From their perspective, you are a copy of them. How would you choose to interact with this "other you" or not? How would you share (or not) your friends, family, or maybe even a lover? How would you share (or not) your clothes and anything else that you own or rent?

  • Imagine you met someone new. And somehow they know everything about you, every thought, every feeling, everything that you know about yourself, they also know (except your passwords). Would you feel very safe or very unsafe with this person? Why?

  • When did you first feel any desire for sex? What stimulated it? How did you feel about yourself for having it?

  • When did you first masturbate?  How were your thoughts and feelings about masturbation? How did they change over time?

  • What are your feelings about S&M? Have you ever participated in that or something similar?

  • How have your ideas about your own sexual expression changed over your lifetime?

  • How old were you when you first had sex?  What were the circumstances?

  • What level of sexual expression do you think is okay for a woman/man?

  • [To a woman] What were your thoughts and feelings when you had your first period?

  • If you imagine making love with a member of the opposite sex, what different thoughts and feelings do you have about that?

  • If you imagine making love with a member of the same sex, what different thoughts and feelings do you have about that?

  • Tell me about the most sexually passionate experience of your life.

  • If you knew for certain you were going to die in exactly 15 minutes from now and there would be absolutely no pain in the process (it would be just like going to sleep very quickly), what would your thoughts, feelings, and actions be in those 15 minutes?

  • Imagine that you had been just diagnosed with a terminal disease. You are in a fair amount of pain already and the prognosis is that the pain will only get worse as the disease progresses. However, it could take more than a year before you die. If you had a easy and sure way to painlessly kill yourself (just by breathing pure nitrogen from a plastic bag that covers your head), would you do it? Why? Or why not?

  • If you knew that, if you continued to see me, we would be making full love within four months from now and you would fully enjoy it and feel good about making love with me, would you choose to continue seeing me now – or not?

  • Here is a fantasy question with five suppositions:

    • 1)       Imagine that whatever you choose to do everybody will totally approve and applaud you for doing that.

    • 2)       Imagine that you have total free time to do whatever you like and all the money you want and need.

    • 3)       Imagine that there are a hundred very charming men/women (choose the opposite sex, if you are heterosexual) who totally admire and adore you and would give anything in the world to be your boyfriend/girlfriend/lover.

    • 4)       Imagine that all these suitors have no jealousy, such that, if you choose to be with more than one, each is just grateful that he or she has whatever time they can have with you.

    • 5)       Imagine that there are no worries about pregnancy or sexually spread diseases.

    • Under these conditions, how many different boyfriends/girlfriends/lovers would you choose, what process would you use to choose them from the one hundred available, and how would you arrange them in your life?

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