Words by Dinithi Perera
Art by Xiaomei Yu

Talking to people is hard, period. Now insert a generation gap and having a genuine conversation can seem almost impossible.

What do you talk about when you can’t rely on relating to mutual millennial specific burnout stress and existential driven hopelessness aha ha ha? Worry not! Conveniently, here are over 30 questions you can ask people, young and old when you want to connect with someone but don’t know how. That’s right, awkward stilted conversations with your grandparents are a thing of the past.

Questions to ask someone older (and probably wiser) than you are:

1. What were you doing at my age?
2. What’s your favourite pastime and why?
3. What is your favourite part of your daily routine?
4. What was the wildest thing that you did in your 20s?
5. What’s the most important thing that you’ve learned over the course of your life?
6. What’s your most prized possession?
7. How would you describe love to someone without using the word ‘love’?
8. If you could go back in time what year would you travel to?
9. Tell me about a turning point in your life.
10. What is your favourite memory?
11. If your life was a movie, what genre would it be?
12. What makes you happy?
13. What is your first memory of grief?
14. What are you still curious about?
15. What defined ‘adulthood’?
16. Who do you miss?
17. Did you have any nicknames when you were growing up?

Questions to ask the youngins (and nothing about school because that’s boring):

1. What is your favourite colour and why?
2. What are you most afraid of?
3. If you could be friends with any fictional character who would it be?
4. If you could change one thing about the world, what would you change?
5. What is your biggest regret?
6. What defines ‘youth’?
7. When have you been adventurous?
8. What’s something you would like to do with all your friends?
9. Do you have a favourite dream, what was it about?
10. What would your perfect day look like?
11. What is a nostalgic song for you?
12. Who is your hero?
13. If you could live anywhere, where would you choose?
14. What is your biggest pet peeve?
15. What is something you don’t know yet?
16. How would you like to be remembered?
17. What is your proudest moment?