FIVE
QUESTIONS

Twenty questions. Four relationships. Free to read, free to screenshot — and built to be sent to one person.

A new set every Friday

The sets

Your sibling

Five questions you should ask your sibling, but you don’t.

  1. What’s something you’re going through that I wouldn’t know about right now?
  2. Do you think I understand the person you’re becoming, or only the version of you I grew up with?
  3. What’s one thing you wish we spoke more about as siblings?
  4. When do you feel closest to me, and when do you feel most distant?
  5. What’s something you hope never changes about our relationship as we grow up?
Question 2 is the one that costs something. It is also the one people write back about.
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Your mother

Five questions for the woman you know completely as Mum, and barely at all as her.

  1. Mumma, when you were our age, what were you like as a teenager?
  2. What’s one thing you always wanted to do but never got the chance to?
  3. When you were a kid, who did you talk to when you were sad?
  4. Both of us know you as the person who is always trying to do every single thing for us. Besides that — what’s one very important thing about you that we still don’t know?
  5. And last, the most important one — Mumma, aaj kya banaya hai?
Question 4 is the one that costs something. Question 5 is there so the conversation ends laughing.
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The person you’re long distance with

Five questions for the call you were going to have tonight anyway.

  1. What’s something from your day that you’d never think to tell me?
  2. When in the day do you miss me the most, and when do you not think of me as much?
  3. What are you not telling me right now because you don’t want me to worry?
  4. What does the version of us that isn’t long distance look like to you?
  5. What’s one thing that would make the distance feel a little smaller this week?
Question 3 is the one that costs something. Question 4 is the one that makes the rest of the call easy.
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The person you keep meaning to text

Five questions for reconnecting, when it has been long enough that starting feels awkward.

  1. What has life really looked like for you lately?
  2. What has changed since we last properly spoke?
  3. What are you excited about right now?
  4. Is there anything you wish you’d checked in about?
  5. How can we stay in each other’s lives this time?
Question 4 is the one that costs something. Ask it before question 5, not after.
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Every Friday

A new set lands here every Friday.

Read them here whenever you like. Or put your email in below, and each new set arrives the day it goes up.

A note on what this is. These are conversation starters, not therapy, and not an assessment of anyone. Nothing here diagnoses a relationship or tells you what is wrong with one. Ask what you want to ask, skip what you don’t, and let the other person do the same.

If you or someone you are about to send this to is in distress and needs to speak to someone now: Tele-MANAS 14416 (India, free, 24×7), or find a line in your country at findahelpline.com.

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