Go deeper? 20 fun questions for an in-depth conversation

It probably sounds familiar to you: the conversations about the work that is piling up, the children who are growing up so quickly, the bad weather or next summer’s holiday destination. Isn’t it more valuable to replace these safe, but boring, conversation topics with in-depth conversations? We will give you a helping hand and share 20 questions for an in-depth conversation.

Tips for an in-depth conversation

We understand that it is not always easy to have an in-depth conversation. And you certainly don’t have to go into depth with everyone, but if you do want to do so, we have a number of tips:

• During an in-depth conversation it is essential that you delve into the other person, so ask further than “how are you?”.
• Don’t get stuck in generalities, but tell or ask something specific. That way you really talk about something, instead of those less-than-meaningful “yes, work is going well” conversations.
• Do you feel comfortable with the other person? Then tell us something personal about that moment in your life. In this way you make yourself vulnerable, which in many cases leads to the other person being more willing to share things.
• Give your sincere attention. Show that you are interested in the other person and ask in-depth questions.

“By engaging in meaningful conversations, we manage to give meaning to a quite chaotic world. And interpersonally, when you find this meaning, you bond with your interactive partner, and we know that interpersonal connection and integration is a fundamental basis of happiness.” – Matthias Mehl in The New York Times.

20 in-depth questions

1. What makes you happy?
2. How do you see the future?
3. If money wasn’t an issue, where would you want to live?
4. What are you most grateful for?
5. What does your perfect day look like?
6. What do you think is the nicest compliment to receive?
7. Who knows you best?
8. What negative trait would you like to change?
9. How are you really doing?
10. Why do you think we were brought into this world?
11. What do you prefer to do when you are alone?
12. How do you see life in 10 years?
13. What’s the best advice you’ve ever received?
14. If today were your last day, what would you regret not doing?
15. What do you want to achieve next year?
16. What characteristic of yourself are you proud of?
17. How do you communicate your emotions?
18. What makes you happiest?
19. How does it feel for you to say “no”?
20. Do you ever miss your younger self?