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120 Deep Conversation Starters To Spark Fascinating Chats

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

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Deep conversation starters are ideal questions to ask if you’re with a friend or a group of friends and you want to get to know each other more intimately.

The problem is, it can be hard to think of the right topic, or you might feel weird about bringing up a controversial one!

In this list of deep conversation topics, you’ll find many questions in varying levels of depth. As there are so many, you’ll find a question that’s right for you and your friends that’ll springboard you into a deep conversation.

The questions are clear and concise, and sometimes have extra questions attached to go even deeper on that topic. Don’t like the question? Then skip and move on. There are 120 deep topics to talk about so there’s plenty to choose from!

These deep conversation questions are perfect if you’re trying to get to know someone better or haven’t seen a friend for a while and want to break the ice and get back to the way things used to be.

Enjoy your deep conversations!

Best Deep Conversation Starters

If you want to learn what makes your friends or new acquaintances tick, asking some deep questions usually does the trick.

While questions to get to know someone can be used when you first someone, these conversation starters are best used for someone you’re familiar with.

They’ll allow you to understand what makes someone tick and open up some fascinating conversations too.

  1. Who has most impacted your life?

2. Is it right for social media to censor certain opinions from being shared? What should happen if those viewpoints are shown to be correct later?

3. Are there any key changes you think you need to make to become the person you want to be?

4. How would it affect society if euthanasia was legal?

5. What’s more important – tremendous skill or high moral character?

6. Is there a danger to society progressing too fast?

7. Do human beings have a role on Planet Earth or are we just a plague on its surface?

8. Do good and evil really exist? If so, where do they come from, and do they change? If not, what does that mean for imposing morals on others?

9. Is bitcoin the future of money or do you think it’s just a fad?

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10. Is everyone equal? Are we equal in some ways but not in others?

11. What excites you the most about the future?

Next: Open-Ended Questions

12. Can anything be forgiven or are there certain things that can never be forgiven? Is this down to personal choice? Where do you draw the line? If you don’t forgive someone, can that actually cause you pain and difficulty?

13. Are people born talented or is that something that’s learned over time?

14. Is there anything you believe or think that’s considered weird or a conspiracy?

15. If you traveled back in time to 100 years ago, what would be your greatest struggle in living back then?

16. What five words would you use to describe yourself? What five words would you use to describe each other?

17. Do human beings gravitate more towards evil or good?

18. Do people really have souls? What about animals? What part of you is a soul and what part of you is something else?

19. Are tribes, groups, or cliques a good way for people to find meaning and commonality or a way of pushing others away and creating an ‘us and them’ mindset?

20. Can we ever be certain that what we are experiencing is really happening? Can we never be fully certain?

21. Does any part of us exist forever?

You might also like: Questions to Ask Friends

22. If you’re not religious, but had to take up a religion, which would you commit to? If you’re religious but had to choose another, which would you choose or would you be an atheist instead?

23. Can obsession ever be a good thing or is it always destructive?

24. What memory in your life still causes you pain?

25. What was your best day and what was your worst day?

26. Do you have a positive outlook on where society is going, or are you negative about it?

27. What’s your opinion on how much media we consume today as a society in terms of TV and social media?

28. What means the most to you? Career or family?

29. If you had to live somewhere else in the world, where would you live and why?

30. How are we helping or hurting the human race as a whole right now?

31. Are you someone who generally puts a lot of effort into living your life, or do you take the easier roads with most things? Why?

32. Do you get bored or do you usually find things to occupy yourself? If you don’t, what do you often do about it?

33. Are there any decisions you think back to and wonder what would have happened if you’d made a different one?

34. If you had to choose absolute free speech or absolute censorship from the government, which would you choose and why?

35. What are your biggest life goals? What’s stopping you from achieving them?

36. If you could take memories out of your brain, which would you remove?

37. What skill or talent would you like to be good at? What’s stopping you from being good at them?

38. What’s a core belief that you make decisions from? Do you ever worry your core belief is wrong?

39. Who’s your best friend? Who’s your closest friend? If they’re not the same person, why do you think that is?

40. What rules would you give your children that you wish your parents had given you?

Deep Intellectual Conversation Starters

If you’ve run out of Questions About Philosophy to ask someone, then you can resort to these intellectual deep conversation starters instead.

They throw up questions that will reveal the ethics and personal beliefs someone holds. All of which will make for some fascinating conversations.

41. Who is the evilest person in the world? Do you think you have the capacity to be that evil?

You might also like: Questions to Ask Old People

42. Describe your perfect home. What do you think it tells you about your character? What answers do your friends give that tell you about theirs?

43. At work, do you prefer simple tasks or challenging ones?

44. When war or famine comes, art and entertainment are the first to go. Do you think art always has a place even when people are starving?

45. What does faith mean to you? Is there a place for faith in modern society? How do you define it?

46. In what big ways has society changed due to covid that will impact us for many, many years?

47. Do you think there’s a disparity between the way we look at caffeine and alcohol and the way we view drugs like marijuana?

48. Would you trade a year of your life for the best week ever? Which is more important to you, time or experience?

49. If religion did not exist at all, what would the world look like?

Next: Hypothetical Questions

50. Today we have much more choice over who we are, who we have relationships with, what jobs we have, and whether we have families or not – do you think there comes a point when too much choice is actually damaging to us?

51. How has the internet changed the world for the better? How has the internet changed the world for the worst? How has it changed you?

52. As human beings, do you think we need to be given more rules on what to do or what not to do?

53. How would you solve the homeless problem in your country? What do you think is the root cause?

54. Should vaccines against diseases be mandatory? When are civil liberties more important than safety?

55. What figure has lived the most meaningful and beneficial life?

56. If you were the leader of your country, what would you change or implement to make individuals or the wider society better? Can there be a clash of interests for individuals and wider society?

57. If you could change one thing about your personality, what would you change and why? If you could change one thing about someone else, what would you change and why?

58. Is food mainly something to give you the energy to get on with your day, or is sitting down to have a meal a big part of your day?

59. What unsettles you the most about the world right now?

60. Is there a difference between someone believing in Jesus Christ as God and believing that the Jedi are real?

61. Do you believe in miracles? How do you define them?

You might also like: Ethical Questions

62. What do you wish you’d done when you were a child that would benefit you right now?

63. What historical event would you go back in time and live through if you could?

64. Is it right for you to spend money on luxuries when people are homeless and starving around the world?

65. What was the most important event to shape your life or your country?

66. What’s your greatest fear and where did it come from? Do you know if you can work through it?

67. Has your personality been constructed slowly over your life or is it something you were born with?

68. When you think about the world, what makes you most happy? What makes you most sad?

69. What do you most admire about the members of your family or your friendship group?

70. Who knows you best in your family or your circle of friends?

71. Do you work to live or live to work? Why is that? Is that down to your job or your personality?

72. Who do you look up to and why?

73. Do you think colonizing Mars is a good idea? If not, why and what could go wrong?

74. What small changes would you implement to make your life better? Why haven’t you implemented these changes already?

75. What’s your biggest regret and would you go back in time to change it? Could you change its effects in some ways now?

76. Who would you want to save the life of and why? Have you saved someone’s life?

77. Do opposites attract, or is that a myth? Do you see this in friends and family relationships?

78. Does life have meaning? If yes, what? If not, can you find your own meaning anyway?

79. How have you changed your character or an aspect of yourself to suit someone else?

80. If death isn’t the end, how would that change the way you live your life?

Personal Deep Conversation Starters

This collection of deep conversation starters is more personal than the rest. These Personal Questions are best used around people you’re familiar with, such as close friends or family, rather than a new acquaintance.

You can give them a try with someone you’ve just met if you want. But you might be better off asking This or That Questions before you get too personal.

81. How do you want people to remember you?

Next: Funny Questions To Ask

82. If you could change someone else’s decision in your personal history, what would it be and why?

83. Is it hypocritical to be a vegan because you believe meat is murder but be pro-abortion? Is killing human life and animal life the same or not?

84. Would you prefer to die sacrificing yourself for someone else, or peacefully at home in bed?

85. If you had to live in blistering hot weather or freezing cold weather for the rest of your life, which would you choose?

86. Would you rather become a billionaire for the rest of your life but remain single without a long-term committed relationship, or be poor but have the most satisfying long-term relationship you could imagine?

87. What do you miss from your childhood? Is there any way of getting it back or would you want to leave it in the past?

88. What is something that doesn’t disturb most people, but really bothers you?

89. How do you deal with stress and anxiety? Do you deal with it well or badly?

90. Are possessions good or bad? Where’s the line between too little and too much?

Next: Questions That Make You Think

91. Would you live ninety days of happiness or ninety years of sadness?

92. If you tried to make every moment of your life meaningful would that be liberating or stressful?

93. What was the biggest adjustment you had to make upon visiting another country?

94. How have you most embarrassed yourself in a social setting? Was it entirely your fault?

95. Who is the most morally good person in the world? Do you think you have the capacity to be that good?

96. If you had to lose one sense, which would you choose? How would it negatively impact your life?

97. What is accepted in wider society right now that will be considered wrong in the future?

98. What’s the scariest thing you’ve ever had to do? Would you do it again?

99. What do you think is your greatest personality trait? What’s your friend’s greatest?

100. If you had to choose only small talk or deep conversations for the rest of your life, which would you choose and why?

101. What’s the difference between killing and murder? Is there one?

You might also like: Good Questions to Ask

102. Who annoys you the most? Why do you think that is? Is there a personality clash?

103. Would you prefer to give up sleep or food if you could live without either one?

104. Which would you choose between – the best TV or the best cinema trips for a year?

105. Describe your perfect vacation. What do you think that tells you about your personality? What do others’ answers tell you about theirs?

106. What will cause the end of the world? War, hunger, or climate change?

107. What gets you the most passionate in life? Why is that?

108. If there is a third world war, where will the main threat come from and where will the lines be drawn?

109. How have people become successful? Circumstance, character, or something else?

110. How much do you read? Would you like to read more? What’s stopping you?

Next: Family Conversation Starters

111. What thing in your life gives you the greatest meaning? Work? Family? Friends? Interests?

112. Is there a book, movie, speech, or conversation that has shaped your life more than anything else?

113. For there to be good does that mean there must there be evil? For there to be evil must there be good?

114. What are your biggest strengths? What are your biggest faults?

115. If you could remove one emotion from human beings, which would you choose and why?

116. Is free will real or just a societal construct? If it’s real how do ultimately make decisions? If not, can anyone be held accountable for their actions?

117. If you could snap your fingers and change your life, what would your life be like?

118. Is the pursuit of happiness the most important thing? If not, what’s the most important thing?

119. If the world was ending in a week, what would happen to society?

120. Can right exist without wrong? Can wrong exist without right?

Looking For More Questions?

Christmas Conversation Starters – If you’re looking to get a conversation started with family and friends over the festive period, this is the perfect set of questions to ask over the dinner table and at a Christmas party!

Open-Ended Questions – A set of questions designed to lead to long and interesting conversations.

Deep Questions to Ask – More topics and ideas that will lead to some interesting talking points.

Thanksgiving Conversation Starters – Some fantastic questions you can use around the dinner table in November.

Mind-Blowing Questions – Some questions that will have you scratching your head in amazement!

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.