32 questions to ask almost anyone

By dkl9, written 2024-229, revised 2024-229 (0 revisions)


Conversation is basically good, but requires a starter, which can easily take the form of a question, of which I often found I have too few readily usable. Inspired by the New York Times' 36 questions by which to fall in love and jacobjacob's "Babble challenges", I thought of and wrote down 51 questions, intending that you can ask each one of most people, with little context or prior familiarity with the person.

Here, then, is an interview-like list of questions for almost anyone, pruned, reordered, and edited from the original 51.

§ Standard stuff

  1. What's your name?
  2. What's your occupation/job?
  3. What's your hobby/art/side project?
  4. Who's in your family?

§ Hobbies

  1. How do you share your art/side projects?
  2. What are your favourite subjects?
  3. What book(s) have you read recently, and loved or hated?
  4. What book/movie/TV/music/etc is both actually good and currently very popular?
  5. What would you do with a week of surprise vacation?
  6. What song is stuck in your head?

§ Stories

  1. What happened when (as effect or as cause) you didn't use your phone for a while?
  2. When did you get your phone (first or current)?
  3. Tell me about something new, funny, or scary you did in the past month.
  4. What happened in the past month that you'll remember for a year to come?
  5. Where are you from (by childhood or by ancestry)?
  6. What languages do you know (at whatever level)?
  7. What are you doing here?
  8. Tell me about a major journey you went on — to where, and what happened?
  9. What event/time period really changed the world?
  10. How did/do you learn geography?
  11. Why did the chicken cross the road?
  12. What colour is the ideal crayon?

§ Preferences

  1. When should one talk to you as I'm doing now?
  2. What am I doing wrong now?
  3. What are your favourite verbal games?
  4. What style of humour do you enjoy?
  5. What things best decorates your home?
  6. What's your favourite sound?
  7. What do you wish was easier?
  8. What do many people do that you see as bad?

§ Deep stuff

  1. How do you know your religion is true?
  2. What's wrong with your religion?
  3. What's obvious/important to you/a culture you're from, but minor to/disagreed on by many people around here?
  4. What should people be aware of more often?
  5. Which one thing (physical or mental) would, if removed, most break you?
  6. Which one thing (physical or mental) would, if introduced, most better you?
  7. What were your mistakes?
  8. Why haven't you achieved your goals?
  9. What do you fear?
  10. How do you respond to mistakes/misery?
  11. What do you want to know about me?

§ Usage notes

Questions 11-16, 23-26, and 31-38 are ordered in adjacent pairs of closely-related questions. Only ask one in each pair in a single conversation. I titled this "32 questions", rather than the naively-counted "41 questions", for exactly this kind of duplication.

If you ask many of these questions, the order here may be good enough, but it's kinda arbitrary. Reorder as you see fit, tho questions 31-41 (deep stuff) are better saved for later. Jump between categories more than the order suggests. Skip questions you see as dumb or irrelevant.

In the questions, "I" refers to the questioner/interviewer, and "you" to the interlocutor/interviewee.

If your goal (as mine) is conversation, forget about getting thru the list. Ask further in response to answers, as they interest you; deviate from the suggested "next" question.