38 Questions To Ask When You Want To Truly Get To Know Someone

Jorge Flores

People are like onions.

We show our best selves on the skin, hoping to get people to like us. To accept us.
We put on makeup. We dress up semi-formally. We hand out our business cards with a beaming grin. We polish our car(s). It’s these kind of “desirable” qualities that we feel completely secure about opening up to others.

But when it comes to the things that truly make us who we are, like our dreams, beliefs, feelings, emotions, thoughts, wishes and fears, we close ourselves up like a clam.

How can we ‘innocently’ break people out of this protective shell and get them to open up to us? So we can understand their true personality and capabilities?

Ask them personal, thought-provoking questions.

Questions that are fun, casual, intriguing, and don’t hint any signs of manipulation.

1. If you could have superpowers, would you use it for good or for evil?

2. How old would you be if you didn’t know how old you are?

3. Would you accept the gift of reading other people’s minds if it meant you could never turn it off?

4. If the average human life span was 40 years, how would you live your life differently?

5. Do you think crying is a sign of weakness or strength?

6. Would you rather be able to eat as much as you want with no weight gain, or require only 3 hours of sleep a day?

7. If you had to choose to live without one of your 5 senses, which one would you give up?

8. In what ways are you the same as your childhood self?

9. If you had your own TV network, what would it be about?

10. If you’re in a bad mood, do you prefer to be left alone or have someone cheer you up?

11. Would you rather know without a doubt the purpose and direction of your life or never have to worry about money for the rest of your life?

12. If you could master one skill you don’t have right now, what would it be?

13. What song typifies the last 24 hours of your life?

14. What words would you pass to your childhood self?

15. If you had to do it over again, what would you study in school?

16. If you could have any accent, which one would it be?

17. Would you rather be married in an arranged marriage or spend the rest of your life single?

18. If you could be someone of the opposite sex for a day, what would be the first thing you do?

19. Would you rather have an extra hour everyday or have $40 given to you free and clear everyday?

20. If you were to be stranded on a deserted island with one other person, who would it be?

21. What would you do differently if you knew nobody would judge you?

22. Would you rather spend 48 straight hours in a public restroom or spend the next 2 months taking only public transportation?

23. What did you learn in school that has proven to be the least useful?

24. If you had an extra hour every day, what would you do with it?

25. Would you rather lose your sense of taste and small or lose all of your hair?

26. If you could invent something, what would it be and why?

27. Would you rather have more than 5 friends or fewer than 5 friends?

28. What stands between you and happiness?

29. If today were to be your last day in your country, what would you want to do?

30. Would you rather lose all of your old memories, or never be able to make new ones?

31. What was the last thing you got for free?

32. Would you rather be extremely attractive or be married to someone who is extremely attractive?

33. What do you want to be remembered for?

34. Would you rather have $50,000 free and clear or $1,000,000 that is illegal?

35. If you could trade lives with one of your friends, who would it be?

36. Would you rather discover something great and share it? Or discover something evil and prevent it?

37. What movie deserves a sequel?

38. If you could see 24 hours into the future, what would you be doing? Thought Catalog Logo Mark

I write what I feel.

Keep up with Tiffany on Instagram, Twitter and misstiffanysun.com

More From Thought Catalog