50 Questions to Ask Someone Instead of “How Are You” (2024)

Everyone who goes to networking events has this challenge: What do I ask someone I don’t know to start a good conversation.

A simple “How Are You?” usually won’t do the trick to bring out the most interesting stories.

Honestly, this is also true for your friends and family. If you only have time for a quick check-in, maybe. But even so, how many times have you heard anyone answering something meaningful?

Kalina Silverman, then a college student, conducted a “little” research project, called BIG TALK. She wanted to be able to make meaningful connections with new people, and realized that takes skipping the small talk to have deeper conversations. She approached strangers and asked them this one question: “What do you want to do before you die?”

She shares her inspiring story in a TEDxtalk, which has already more than 4,400,000 views.

In a previous post I talked about the transformational power of asking questions. Asking thought-provocative or sometimes seemingly “absurd” questions often don’t come naturally.

It simply needs practice.

That’s the reason why I challenged myself to ask all the questions that come into my mind, no matter to whom/what it is, for an entire month. And obviously taking the time to mindfully listen to the answers.

Why don’t you join me?

Would love to hear which of your questions resulted in the most unexpected, honest, mind-opening, and interesting stories.

Have fun with them!

1. What was your favorite moment thus far today?
2. What brings you in a good mood?
3. Describe to a 6-year old what you do in life?
4. What are 3 words that describe you best?
5. What always makes you smile?
6. How do you contribute to a better society?
7. What are the 3 most important aspects to support your lifestyle?
8. When you were little, what did you think you were going to be?
9. What is something you know you do differently than most people?
10. Is there something you need help with at this moment?
11. Is there someone I can connect you with?
12. What are you (un)secretly good at?
13. What talent do you wish you’d have?
14. How do you feel about taking risk?
15. What’s your most (un)healthy habit?
16. If there is anything you would do differently in your life, what would it be?
17. Who would you like to have dinner with tonight (could be anyone, dead or alive)?
18. What genre of book/movie has the most impact on you?
19. Which music genre do you listen to the most?
20. What’s the nicest compliment you’ve ever received? From who?
21. What advice would you give your 20-year old self?
22. What is one life lesson that you think everyone should know?
23. What’s your biggest fear that you’ve overcome?
24. What was the most dangerous situation you’ve been in?
25. What’s the most unbelievable thing that’s ever happened to you?
26. Where would you live if you had no ties to any specific place?
27. What was your favorite subject in school?
28. What was the last book that you read?
29. What have you never done before?
30. What time did you wake up this morning?
31. What was the first thing you did this morning?
32. What was the best gift you’ve ever received?
33. When was the last time you said “I love you” to someone other than your partner?
34. What is your earliest childhood memory?
35. What did you love doing as a child that you don’t do anymore?
36. What was your last dream about?
37. How do you relax yourself when stressed out?
38. How do you unlock your creativity?
39. What is your favorite meal of the day?
40. Where was the last place you’ve visited?
41. What do you do when you have to wait (e.g. at the doctors)?
42. Which TV show are you following right now?
43. How often do you talk to strangers?
44. What was the last picture you took?
45. What’s your favorite drink?
46. If money wasn’t an issue, how would that make your life different?
47. Have you ever done something competitively?
48. Who do you ask for advice when you have to make a difficult decision?
49. What’s your favorite thing you have at home?
50. What’s your favorite way to travel?

That should be a good start ain’t?

It’s up to you now.

Don’t think, just ask!

Byebye to shallow “How are you’s”

Love to hear your stories!