48 Thoughtful Questions to Get to Know Someone Better

Here’s a list of questions that you can ask when you’d like to get to know someone better. Some of them can be used when you meet a person for the first time, while others may be more suitable to ask someone that you already know.

But either way, by asking these questions, you’ll learn more about a person’s values, what motivates them, as well as how they feel cared for. And because of these reasons, the questions can also be used as icebreakers at social gatherings.

In fact, with some of the questions, the person may even respond by saying, “Wow, What a thoughtful question! I don’t think anyone has ever asked me that before.” And with that said, here are the questions that you can ask:

1. What is one thing that you own which you’d want to keep forever?
2. If you could’ve witnessed any event in history, what would it be?
3. What’s your favorite quote?
4. What accomplishment are you most proud of?
5. Do you have any nicknames?
6. What is something that you consider to be beautiful?
7. If you could be the student of any teacher or expert, who would you most want to learn from?
8. What are three things that really bring you joy?
9. Who inspires you to be a better person?
10. If you’ve had a rough day, what is the best thing that either you or someone else can do to cheer you up?
11. What’s one thing that you still want to accomplish in your lifetime?
12. What is your favorite way to relax?
13. What’s the kindest thing that someone has ever done for you?
14. Have you ever met a famous person?
15. What is one thing you do very well?
16. Complete this sentence: I wish everyone would ___________.
17. What idea do you feel is worth having a spirited debate about?
18. What is one thing that others often seek your input about or help for?
19. What is something quirky about you that you’re willing to admit?
20. What piece of wisdom would you like to pass on to others?
21. What is a question that you like other people to ask you?
22. What’s one thing that you’re truly fascinated by?
23. Think of the best community that you’ve been a part of. What made it so great?
24. If you had a pick a song for your “entrance music” (like a professional wrestler), what would it be?
25. When’s the last time you did something you thought you couldn’t do? When were you brave?
26. What’s one thing that is important for others to know about you?
27. What is your latest victory in life?
28. When was the last time you felt really good about yourself? What was happening?
29. What’s something that made you experience wonder or awe recently?
30. What’s one piece of good news?
31. What would be the best compliment that someone could give you?
32. What trait do you most admire in someone else?
33. How would you want others to describe you?
34. What is one book that has changed your life somehow?
35. What do you look forward to each day?
36. Where is the most relaxing place you’ve ever been?
37. What’s definitely worth spending more on in order to get the best?
38. What fad or trend do you hope comes back?
39. On a scale from 1 to 10, how is your day going? What would make it a 10?
40. What do you like to do the old-fashioned way?
41. What’s the story behind that (shirt, sweater, hat, scarf, tie, bracelet, etc.) you’re wearing?
42. What concept do you try to explain, but often feel misunderstood when you do?
43. What is your ideal environment to live in and why?
44. What’s overrated? Underrated?
45. What’s something you didn’t want to do at first, but are now glad that you did?
46. What’s the best meal you’ve ever had?
47. What makes you feel “at home”?
48. How do you like to pass the time on a long (airplane, train, car, etc.) trip?