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a workbook · riadms.com

the deeper questions

twelve questions for two people, in three rounds, and each round goes a bit deeper than the last. built on the order from a 1997 closeness study, written as my own set.

sit with one person you want to be closer to: a partner, a friend, or someone new. take turns reading a question out loud, and both of you answer it. go in order and do not skip ahead. the order is the point: nobody gets asked the deep question before they have had the easy ones.

  1. 01

    what did you change your mind about this year, and what changed it?

    round one stays on the outside of your life. easy to answer, and still more than how was your day.

    from me this is the warm-up. if it feels too light, good. it is meant to be.

  2. 02

    what is a small, boring part of your week you would miss if it went?

    the answer tells you what someone’s ordinary life is made of.

  3. 03

    who made you laugh most recently, and what did they do?

    a real person and a real moment, not a type of humour.

  4. 04

    what are you good at that nobody asks you about?

    everybody has one, and it is usually something they are proud of in private.

  5. 05

    tell me one thing that happened this month. then tell me what it did to you.

    round two moves from what happened to how it felt. that is the move that makes people closer.

    from me the second half is the question. the first half is only there to get you to it.

  6. 06

    who was there the first time something big happened to you, and do you still talk to them?

    this is the person who knows the story without the preamble.

  7. 07

    what do you want more of from the people in your life, and have not asked for?

    say the thing, even if it sounds small.

  8. 08

    when did you last feel understood exactly right, and what did the other person say?

    pay attention to what they did, because it is probably what they want from you too.

  9. 09

    what do you believe about yourself that you have not said out loud to anyone?

    round three is the accurate version. answer only as far as you want to.

    from me you are allowed to say "i am not ready for this one." that counts as an answer.

  10. 10

    what do you think i have slightly wrong about you?

    close people are more sure they understand each other than they actually are. this is where you check.

    from me a study found married couples were no better than strangers at reading each other’s ambiguous sentences. they were only more confident.

  11. 11

    what would you be scared i would think less of you for?

    when they answer, the only job is to stay.

  12. 12

    what have you noticed about me that you have never told me?

    end on something the other person gets to keep.

after the last round: which question was the hardest to answer, and what did you learn about them that you did not know this morning?