57 Interesting questions to ask someone

For some, talking to people can be tough. For others, it flows naturally.

Have you ever clicked with someone you just met like you were long lost friends? Or maybe had a very awkward moment with someone new?

They both happen to all of us some time in our lives. To put it simply, every relationship, be it friendship or a significant other, starts with a conversation. And conversations generally start with interesting questions.

Conversations generally start with interesting questions

Don’t be that boring person who everyone thinks is awkward. It’s easier than you think to be a good conversationalist. It all starts with a few good questions. The first impression.

Always think before you speak to make sure you don’t offend anyone and having a list of questions at your fingertips really help.

When the conversation flows, that’s when things get interesting. Questions are not just conversation starters, but they help you avoid too much silence and helps you to get to know people better.

Interesting questions to ask people

These questions are sure to make you a bit more popular than you are right now. Try out a few and see where they take you!

  1. What’s your favourite attribute about yourself?
  2. Who do you admire a lot but don’t want to be like?
  3. What are you most proud of in your life?
  4. How many seasons/episodes would you last if you were a Game Of Thrones character?
  5. Best compliment someone gave you?
  6. If you had to change your name, what would you choose?
  7. What was the most surprising thing (to you) you’ve ever done?
  8. Who is your idol? The person you aspire to be like one day?
  9. What’s the cheesiest pick up line you’ve used or someone has used on you?
  10. Who’s your favourite Disney character?
  11. Which bad habit of yours do you find the hardest to let go?
  12. What do you often do that is normally for ‘old people’?
  13. What’s the most ridiculous goal you’ve ever had?
  14. Give up your phone for a day or coffee for a week?
  15. If you could live someone else’s life, anyone, who would it be?
  16. What did you always wish you could do but never did?
  17. What was your favourite cartoon growing up?
  18. What’s your go to song?
  19. What food do you think about all the time?
  20. Best memory as a child?
  21. What’s quote do you live by?
  22. What’s the longest you’ve stayed awake? What were you doing?
  23. What personality trait do you wish you had more of?
  24. If someone were to create a movie of your life, would it win an Oscar?
  25. What’s the worst thing you did when you were a kid?
  26. What question would you hate answering?
  27. What’s the weirdest thing you’ve ever tried?
  28. Do you like telling people ‘I told you so’?
  29. What’s the most boring thing you’ve done yet you continued doing it?
  30. What’s the dumbest thing you’ve argued about?
  31. If you could create a law for one of your little pet peeves, what would it be?
  32. What is the weirdest thing your friends say about you?
  33. What’s the biggest lie you’ve ever told?
  34. What is the most absurd thing you’ve spent money on?
  35. What’s something that is incredibly expensive and you know it, but you still spend money on it?
  36. What’s the best bank you’ve ever seen live?
  37. What show or movie can you watch over and over without getting bored of?
  38. If you were arrested, would your friends and family be shocked?
  39. What’s the biggest thing you’ve ever done for a friend?
  40. What do you and your best friend talk about the most?
  41. Do you have a fact you think I don’t know?
  42. What’s the most expensive thing you’ve ever eaten?
  43. Have you been banned anywhere?
  44. What do you wish your phone could do that it can’t already do?
  45. How long can you last without your phone?
  46. What was your first post on Instagram?
  47. What is a must have in your refrigerator or pantry?
  48. Which is your favourite month in the year? And why?
  49. What’s the biggest amount of money you’ve ever found?
  50. What story about your childhood are you most embarrassed about?
  51. What dish would you love to know how to cook but don’t know yet?
  52. Do you sometimes wish you were still a kid?
  53. What do you always procrastinate on?
  54. What topic could you spend hours talking about and never get bored?
  55. Was there anything you were completely certain of but turned out to be wrong?
  56. What did you love to eat before but now hate?
  57. What’s the most annoying thing anyone’s ever done to you?

There they are. Use these questions as conversation starters or to keep one going. You’ll find that things get more interesting as you hit the mark with some questions. Remember that not all questions will give you a good response but when you get one that gets the other person talking, that’s when you’ve clicked!

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