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120 Hardest Questions To Answer

A photo of Tom who is the Co-Founder of Questions About Everything

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Think of the hardest questions to answer and you’re probably imagining questions related to the universe, ethics and life itself.

Well, we have plenty of these and more in this list of hard questions to answer. Some of these questions are tough and difficult to answer and pose serious intellectual puzzles, while others are more whimsical in nature.

Still, all of them are hard questions to ask anyone and will lead to some interesting and deep conversations.

If you want to wrack the brains of your friends and family, then this set of difficult questions to answer will do the trick!

Hardest Questions To Answer List

1. Are you excited or anxious about the future?

2. What actually makes you who you are or me who I am?

3. What’s the meaning of life? Is there one meaning for all, or does it depend on the person?

4. Failure is measured by others’ expectations and reactions, for instance when you don’t get a job or someone is critical of your work – is this a good way to measure failure?

5. Can we ever know if what we’re experiencing is actually real?

6. How much of what you remember is actually what happened? How sure are you that the past you know is actually the past?

7. Is morality nothing more than a social construct?

8. What would be the most surprising thing to tell someone who lived one hundred years ago about our current era?

9. If you only had the sense of touch and had no other sense, what would your life be like?

10. Are there no absolute truths? If so, then what is ‘truth’ really? If not, then isn’t that statement a truth in and of itself?

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11. We consider human beings as of more value than animals because of our intelligence, but does that then mean less intelligent humans aren’t of as much value as other human beings?

12. What does it mean to have freedom? Do laws and rules create restrictions or greater freedom?

13. Will human beings survive to the next century? If not, what will be our downfall? If so, what will be our savior?

14. How much money would be enough money? Do you think you’d feel the same when you got there?

15. If trees could talk, what do you think they would say?

hardest question to answer on what trees would say if they could talk

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16. Is there a reason we fear irrational things in life? It seems strange considering fear is a defensive mechanism against things that cause harm.

17. Do you think there’s a God? If so, what or who is this God?

18. Would you prefer to know a terrible truth about your life that you could do nothing about, or live in blissful ignorance of it?

19. If humanoid robots could convincingly show they feel pain, sadness, and joy, do you think they’d actually be feeling these things or just giving the illusion of it?

20. How do you give someone advice without telling them to just think and act as you would?

21. If animals fight and attack one another and eat each other, then why do we find the same behavior in human beings so repulsive?

22. Everyone knows we’re all going to die someday, but if we all believed we wouldn’t, what effect would that have on the world?

23. Is it better to have a smaller government with more possibility of people taking advantage of each other for wealth, power, and desire, or is it better to have a bigger government but have fewer freedoms and control over your life?

24. Are you born with a talent or do you gain it over time?

25. If you could only save one of your parents from a fire, which would you save?

26. How would your life be benefitted if you could read others’ minds? How would your life be hindered?

27. If the Big Bang created the universe, what created the Big Bang?

28. The dreams you want to achieve in life, to write a book, become an actor, or climb a mountain, probably won’t look or feel like how you ‘dreamt’ it, so even if you do those things, are you actually ‘achieving your dreams’?

29. Is the lesser of two evils actually morally right? How can it be if it’s still ‘evil’?

30. If you could only have one child, would you want a girl or a boy?

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31. If everyone lived for an average of 170 years, instead of 70 years, how would the world be different?

32. What’s your greatest success? What’s your greatest failure?

33. Someone has committed a violent crime, and you are the judge; you only have two choices, execute them or set them free – which do you choose?

34. What’s something you’re putting off doing in the future, but you secretly worry you’ll never get around to doing?

35. Will you ever be the version of yourself you want to be?

36. Is there anything you want to do with your life, but can’t because you worry about what others will think?

37. What’s your irrational fear? If you know it is irrational, then why are you scared of it? Is there a part of you that thinks it’s not irrational?

38. What would you be sad to not have accomplished when you die?

39. If you suddenly became the leader of your country, how long do you think it would take for you to start having respect for all the leaders that have gone before you?

40. Who has had the greatest effect on your life?

41. What are your most important values/morals? Do they reflect in your actions, and if not, are they actually your most important values/morals?

42. Would you have your legs sawn off if you could then fly/hover instead?

43. If I replaced all the organs in my body, would I still be me?

44. If artificial intelligence could control us all, meaning that no one would die by accident, or get sick, but we had no say over our lives, would that be better than the life we have now?

45. Can you milk a zebra?

Next: Mind-Blowing Questions

46. If tomorrow was your last day alive, what would you do with it?

47. Have you ever been star-struck? What did you do and what happened?

48. How big a house do you want/need?

49. If people call him ‘Pooh Bear’, why is his full name ‘Winnie-the-Pooh’? I mean, who has the word ‘the’ in their name?

50. If you found out your favorite author was a pedophile, would you stop reading their books? If they were still alive or already dead, would it make a difference? What if you already owned all their books?

51. What’s your earliest memory? Do you know for a fact you’re actually remembering what happened, or just remembering images created in your head when people told you about whatever you’re ‘remembering’?

52. Are you a risk-taker? At what point does taking a risk become reckless?

53. When can you imagine you’ll have achieved everything you want to do in life?

54. What are you most skilled at? What are you worst skilled at?

55. What’s the difference between infatuation and being in love? To love is a decision and involves sacrifice, so if you ‘fall out of love’ and leave the person, were you ever ‘loving’ them in the first place?

56. Has anything ever happened to you that you can’t explain rationally? Could you try to explain it?

57. When have you felt that you were exactly where you were supposed to be, or doing exactly what you should be doing?

58. If you could live three hundred years as an old person starting now, or the rest of an average-length life feeling and looking 21, which would you choose?

59. Where do you want to be living, working, and generally doing with your life in ten years’ time?

60. What are the defining moments of your life?

Next: What if Questions

61. Is being happy the most important thing? What about the happiness of others?

62. What kind of things would you like to be said at your eulogy?

63. Is there anything you feel is holding you back in your life, in some way, shape, or form?

64. If social media communication was all videoed instead of writing, so you could actually see the other person, do you think it would change what people say to one another?

65. What do you think about most of all when you lay awake at night not being able to sleep?

66. What in life will we never understand or know anything about?

67. You can fit all of the UK almost three times inside the state of Texas – how was it that the tiny island of Great Britain managed to rule over a quarter of the world at one stage?

68. If you’ve never been somewhere, like the moon, can you ever be completely sure it exists?

69. If life has a meaning, what about individual days – what’s today’s meaning? How about yesterday or tomorrow?

70. Do you look back fondly at the past or are you glad certain times are over?

71. Why are feelings so important to people when they shift and change so much? Can you make decisions based on them?

72. If you could scroll through your thoughts like search history on a web browser, what do you think would surprise you the most?

73. If you could travel back in time to stop a bad thing from happening, what would you prevent?

74. What’s something you’re good at but don’t enjoy doing?

75. What would you be sad to not have accomplished by this time next year?

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76. What would you give up to see your dreams fulfilled?

77. What’s the difference between a journey and a trip?

78. Usually, when two people date, one person has feelings for the other first – in this instance, does that person then coerce the other, at least initially, into feeling something through affection, gifts, and other things?

79. If ninety-eight percent of Antarctica is covered with ice, can it really be called ‘land’?

80. Do you think aliens exist, and if so what do they look like? Have they ever visited Earth? If not, what is the point of the rest of the universe?

81. If the theory of evolution is true, then how will human beings evolve next? What would be a good way, and what would be a bad way?

82. Why do we call bottoms ‘trousers’ or ‘pants’ when it is one piece of clothing connected together, unlike socks or shoes, which are two distinct items?

83. What’s your biggest regret? Did you learn from it, and how has your mindset on it changed since then?

84. There are more people in illegal slavery now than when it was legal in the 1700s and early 1800s – do you think slavery will ever end?

85. After the death of Lawrence Anthony, the man who saved them, a herd of elephants marched twelve hours to his house and stayed silent for two days. One year later to the exact day, they returned – how do you explain this?

86. When do the day’s end and the next ones begin? If you wake up in the middle of the night, what day are you in?

87. Do we have free will, as so much of what we decide is based on our desires or others’ desires? Are we just living by impulse or something more?

88. If you knew where you were going to die, what would make you go to that location anyway?

89. Is it more painful to give birth or pass gallstones?

90. How different would you be if you had different parents?

Next: Self-reflection Questions

91. Why do we spend money on frivolous things like donuts or DVDs, when we could give the money to charity to help people?

92. If you had to go on a reality TV show, which would you choose and why?

93. If there is a God, do you think animals have some relationship with him?

94. Would you prefer to find the perfect person for you, get married, but then one year later, they die, or never have met and married them at all?

95. So much goes into running a clean, functioning society – how often do you think about the sewage system, telephone lines, or health services? Do you take them for granted?

96. If human beings hunt an animal to extinction, isn’t that just us being animals, hunting just as other animals do? What’s the difference?

97. People say they have faith in God, that they believe he exists, but how could we know for sure?

98. Would you prefer to give up social media forever, or have all of your inner thoughts posted online?

99. What does it mean to be alive? Are plants and animals alive? How about a fetus?

100. What if everyone was actually colorblind? How would we know if we weren’t? If we all are, does that mean no one is?

101. If I gave you $1 million and you could go double or nothing on the flip of a coin, would you risk it all?

102. How does the internet work?

103. What do you think your final words could be?

104. Could you just be existing in a dream that your eight-year-old self is dreaming? How would you ever know?

105. What decision that you make today could make your life better in one years’ time?

hardest question to answer on what decision would make your life better

Next: Questions that make you think

106. We haven’t searched the entire surface of the moon, so how likely is it that there are secretly aliens or human beings from the past living there?

107. Would you prefer to be the uglier or more attractive person in a relationship?

108. If you were given all the money you needed to achieve your dreams, but then you found out a disaster in the world needed that exact amount of money for relief, what would you do?

109. Do you work to live or live to work?

110. If you could send one sentence on paper to your past self, what sentence would you write?

111. We are known as human beings, but why aren’t we called human doings?

112. If you became a celebrity how would you keep yourself from becoming vain and unconnected from the real lives of ‘normal’ people?

113. How can you prove to me you’re an honest person?

114. Would you prefer an outside toilet but you have a bath, or no bath, and a toilet indoors?

115. If you can be happy about something awful happening to someone you hate and you can be sad because you’re working through losing someone you loved, how can happiness be better than sadness?

116. If you knew that a bee died every time you ate your favorite food, how often would you have it?

117. When you heard that birds fly ‘south’ for the winter, did you know what that meant or did you think ‘the south’ was a magical, mystical place?

118. There are so many people in this country – how do we have enough space to bury a lot of them in graves once they die? Where do they all go?

119. Will it ever be possible to make dark lamps where they shine out darkness instead of light?

120. If you have a dream for your life, it’ll never be exactly as you imagine, so why do we still try and follow those dreams?

Looking For More Questions?

Good questions to ask – A range of questions that will have you thinking deeply one minute and laughing hysterically the next!

Interesting conversation topics – Some great talking points you can use with anybody.

Deep questions to ask – Some more deep and introspective questions to ask your friends.

Ethical questions – A set of ethical dilemmas for you and your friends to ponder.

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.