Guide

25 questions for a thoughtful written exchange

Updated 2026-11-04 · 4 minute read

The best questions invite a story rather than a list. Use these to start a letter, to reply to one, or to keep a slow conversation going when you are not sure what to ask.

The questions

1. What did you change your mind about this year?
2. Describe a perfectly ordinary day that you would happily live again.
3. What is a small thing that reliably makes your day better?
4. Which place from your childhood do you still think about, and why?
5. What is something you were certain about two years ago and are less sure of now?
6. Who taught you something important without meaning to?
7. What is a skill you are slowly getting better at?
8. Tell me about a meal that you remember for the people, not the food.
9. What does a good weekend look like for you, hour by hour?
10. What is a book, film or song you keep returning to, and what do you find there?
11. What is the kindest thing a stranger has done for you?
12. What do you wish more people asked you about?
13. What is a risk you are glad you took?
14. What is a risk you wish you had taken?
15. Describe a place you would take me if I visited your city for one afternoon.
16. What is something you are looking forward to in the next month?
17. What is a rule you live by that you would not mind breaking?
18. What is the best piece of advice you ignored?
19. What does home smell like?
20. What is something you are quietly proud of?
21. What do you do when you cannot sleep?
22. What is a tradition from your family that you would like to keep?
23. Which of your habits would surprise the people who know you casually?
24. What is a topic you could talk about for an hour without noticing the time?
25. What would you like the next seven days to feel like?

How to use them well

• Answer first, then ask. Share your own answer before you ask the question back, so it does not feel like an interview.
• Pick one. Two questions in one letter is plenty. One is better.
• Be specific. "I like travelling" tells someone nothing. "I once missed a train in a small town and ended up at a wedding" tells them a lot.
• Follow up. Pick a detail from their reply and ask about it. People notice when you were listening.
• Skip the ones that feel too heavy yet. Early letters can be light. Save the more personal ones for later.

Starting points for different moods

Light

Questions 2, 3, 9, 16 and 21 are easy to answer and make good openers.

Reflective

Questions 1, 5, 14, 17 and 25 invite a more considered reply.

Warm

Questions 4, 7, 11, 19 and 22 tend to bring out stories about people and places.

If you want help with the structure of a letter, read how to write a first letter.