50 Questions You Need To Ask To Really Get To Know Someone

We’ve all been at a stage with someone where we feel like we know them, but still have a lot to learn. It could be a hopeful love interest or a friendship in its early development. There’s a lot of questions we tend to have and answers we hope to hear the answers to. By asking these kinds of questions, you’re opening yourselves up for conversation, some of which are on topics that may be uncomfortable for some.

These questions range from the cliché “what’s your favorite color?” to “what is the one thing you’ve secretly hoped someone would do for you?” The answers that can be given are to help you get to know the nitty-gritty details about someone, and see them from a perspective not everyone gets to know.

Ask every one of these questions. Both of you should take turns answering. Take the opportunity to learn about the deeper meaning they have in life and appreciate them for the vulnerability they’re displaying.

  1. What’s the one thing in your life that’s happened to you that made you a stronger person today?
  2. What’s something that’s made you feel small?
  3. Where is one place you feel like you can be 100% yourself?
  4. Where do you go to escape and what do you do to forget about life for a while?
  5. Who has had the biggest impact on you?
  6. What’s one thing you could change about yourself?
  7. Do you feel like you belong in this generation? Why?
  8. Who are you closest to in your family?
  9. Who in your life knows you the best?
  10. What’s your favorite quality about your best friend?
  11. What’s one trait you could steal from your best friend that you feel you don’t have enough of?
  12. What did you want to be when you grew up? What are you doing now? Why did that dream change?
  13. Do you like or hate compliments?
  14. How do you like to be complimented and what do you like to be complimented on?
  15. What is one thing about yourself physically you love? Non-physically?
  16. What’s one attribute you feel you should work on about yourself?
  17. Do you believe in love or soul mates? Why?
  18. Have you ever been in love? If so, how many times?
  19. What makes you fall in love with someone?
  20. How do you know you’re in love?
  21. What does vulnerability mean to you?
  22. If you had the chance to be someone of the opposite sex for a day, what would you want to experience?
  23. What’s one thing you’re afraid to ask the opposite sex, but really want to?
  24. What is the most attractive quality or feature about a man and a woman?
  25. If you could take a class on one historical moment what would it be on?
  26. What’s one thing you would love to learn more about and why haven’t you done it yet?
  27. What is your dream job, considering money isn’t a factor?
  28. What was the last thing you cried about?
  29. What is your favorite memory?
  30. What’s your most embarrassing moment?
  31. What was the last thing that made you laugh?
  32. What was the biggest thing someone did to hurt you?
  33. Do you accept the concept of death or are you afraid of it?
  34. Do you believe in psychics and horoscopes?
  35. Do you believe in religion?
  36. What do you regret the most?
  37. What’s the craziest thing you’ve ever done or wanted to do?
  38. Where do you like to be touched on your body in a non sexual way?
  39. Would you ever tell someone they had food stuck in their teeth?
  40. If you could be in a music video, which song would it be for?
  41. What’s your guilty movie or TV show pleasure?
  42. What’s one thing you’ve always wanted to try sexually but you were afraid of being judged for?
  43. Are you proud of who you are as a person?
  44. How would your parents describe you as a child?
  45. What is the one thing about yourself that you pride yourself on?
  46. What’s one thing you wish you could have more of besides money?
  47. What is one goal you want to achieve by the time you’re 30?
  48. What is the top 3 qualities your future spouse has to have in order for you to get married?
  49. What is your proudest accomplishment to date?
  50. What’s one question you’ve always been afraid to ask me?

The best time to ask these questions would be in a moment where you both feel happy and are at a stress-free part of your day. Like late at night when your hanging out, or when you’re cuddling in bed together.

Take the time to appreciate someone else’s views, engage yourself in an endless and open conversation and don’t be afraid to express yourself in a way you haven’t been before. Whether you like what they have to say or not, you’ll definitely have learned a lot about who they are.

Feature Image via Roamaroo.

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