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100 questions to ask your best friend

Everyone should have a best friend because they are our fellow humans with whom we can talk about almost everything. In other words, sharing things with your parents or siblings can be difficult, but we never hesitate to disclose things with a best friend. They also always encourage us and enhance our self-esteem.

Even if you’ve known your best friend for years, there’s a good chance you don’t know everything there is to know about her. You’ll have plenty to talk about if you use these conversation starters which I have listed just for you! 

100 questions to ask your best friend

  1. What habit of mine do you like?
  2. Why do you think I’m your best friend?
  3. Why are you so cheezy like a rat?
  4. What do you think you are to me? As a person and friend.
  5. What’s your favourite pick-up line someone said to you?
  6. When you’re in need of a pick-me-up, what’s your go-to flick?
  7. What’s your favourite music to listen to when you’re having a bad day?
  8. What would you put on the ultimate sandwich if you could make it?
  9. What qualities do you look for in a friend?
  10. Can a deaf person hear their voice in their head?
  11. What is the most cherished memory you have?
  12. To you, what does friendship entail?
  13. What is the strangest item you’ve ever eaten?
  14. What are the things you don’t do enough of?
  15. Do you suffer from stage fright?
  16. What was it like on your first day of school?
  17. Do you wish you could live in a perfect society?
  18. Are there any trends that you aim to stay away from?
  19. What is your attitude toward technology?
  20. What do you devote the majority of your time and energy to?
  21. Do you have any prejudices that you are aware of?
  22. Have you ever felt as though your world was collapsing around you?
  23. Would you go back in time if you had the chance?
  24. Are you comfortable spending long periods of time alone?
  25. Do you find the beauty in things that other people don’t?
  26. Do you find yourself actually agreeing with the villain on a regular basis?
  27. Do you have any favourite websites that you go to on a regular basis?
  28. Have you ever tried to lose weight?
  29. Did you ever wish you could be an adult when you were a kid?
  30. What is too serious to be joked about, if anything?
  31. What is your proudest achievement in life?
  32. What part of your life does love and affection play?
  33. When was the last time you cried in front of someone?
  34. Are you a believer in fate?
  35. What is your favourite dish to prepare?
  36. Are you a good character judge? Have you ever gotten it completely wrong?
  37. Have you ever sought the advice of a psychic? What went wrong?
  38. Have you ever written a love letter to someone you care about?
  39. What gives you the creeps?
  40. Have you ever thrown a party for someone?
  41. What aspects of yourself would you like to improve?
  42. What is the funniest thing you remember?
  43. What is your prized property, and why is it so?
  44. Is there anything you can’t imagine your life without?
  45. Have you ever quit in a macho style only to then be forced to return?
  46. What’s one traditional dress that you wish didn’t exist?
  47. What lessons did your father impart to you?
  48. What have you learned from your mother?
  49. What is the most memorable gift you’ve ever received?
  50. What is the most fascinating aspect of science?
  51. What is the best monetary investment you’ve ever made?
  52. What is one of your terrible habits?
  53. What do you have reason to be thankful for?
  54. Who do you want to be envious of?
  55. What is one image that will stay with you forever?
  56. Do you believe you’d be permitted into a club where only sexy people are allowed?
  57. What’s the worst tagline you can think of for a wart removal cream company?
  58. What ludicrous conspiracy theory do you believe has the potential to appear logical?
  59. Would it be better to live alone or in a community during the apocalypse?
  60. For a year, a witch has cast a spell on you that turns you into an inanimate, non-electronic object. You must be able to get at least a hundred individuals to touch you in order to be converted back into human form by the end of the year. What inanimate thing would you be if you weren’t alive?
  61. You’ve been committed to a mental institution. What do you say to the folks inside to prove you don’t belong there?
  62. How far does someone’s ownership of a piece of land extend? Is it theirs all the way to the centre of the planet?
  63. Hummingbirds hum because they can’t recall what they’re saying.
  64. Is it possible to see someone’s tears from beneath the water’s surface?
  65. Why are unsolved mysteries referred to as such? Shouldn’t they be unsolved to be dubbed a mystery in the first place?
  66. When chickpeas are neither chicks nor peas, why are they called chickpeas?
  67. When look and sight are virtually synonyms, why do the phrases ‘overlook’ and ‘oversee’ have different meanings?
  68. What was the best gift you’ve ever received?
  69. How often do you check your reflection in the mirror during the day?
  70. What do you bring to a friendship that others don’t?
  71. What’s a dream that keeps coming back to you?
  72. What gives you a sense of security?
  73. What has been the most fortunate event that has ever happened to you?
  74. What do you want people to remember you for after you’ve passed away?
  75. What is the strangest fact you’ve ever come across?
  76. What would you do if you had the opportunity to do anything you wanted for the rest of your life?
  77. Do you have a fear of dying?
  78. What would be the final thing you’d say to me if you found out I was going to die tomorrow?
  79. Which holiday is your favourite?
  80. What is your favourite charitable organisation, and why?
  81. Would you accept an opportunity to travel to the farthest reaches of the universe?
  82. Do you like visiting museums?
  83. When you go to the zoo, what kind of animal do you most want to see?
  84. What would you call your alter ego if you had one?
  85. What would you do if you suddenly found yourself with a million dollars?
  86. Would a person with amnesia remember that they had no recollection if they were suddenly cured?
  87. Before there were dictionaries, where did dictionary creators go for the meanings of words?
  88. Why do we refer to it as “after dark” when it is truly “after light”?
  89. Is it necessary to make an appointment with a psychic, or would they come to you?
  90. Why does a grapefruit have nothing in common with a grape in terms of appearance and flavour?
  91. If it’s intended to be SELF help, why are there self-help groups?
  92. Is it true that penguins have knees?
  93. Why do they say “give my two cents” when your thoughts are only worth a penny?
  94. Is it possible to ruin milk by pampering a cow and lavishing it with gifts?
  95. Why is sleepiness listed as a sleeping pill adverse effect?
  96. What was the goal of the first person who milked a cow?
  97. What is the most egregious fashion blunder you’ve ever made? Is there a photograph of it?
  98. What holiday would you invent if you could?
  99. What was the last book or series you wished you could live in?
  100. What would you do if you could be the best in the world at something?

The bottom line

When you’re bored and want to learn more about your best friend, ask them these 100 questions. 

They can also be used to spice up a mundane chat. Make sure to let me know which questions you picked.

About the Author

Sasha Aun
Sasha Aun
Hi, I am Sasha, a professional relationship expert, and a blogger. At Datinghelpguide, I write tips to create an attractive dating profile and guides on managing dating profiles on multiple apps.