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120 Deep Personal Questions To Ask Someone

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

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If you truly want to get to know someone, then these personal questions to ask anyone will come in handy at some point.

Whether you know that person really well, or you’re newly acquainted, our collection of deep personal questions will help to find out what makes them tick.

These are more insightful questions than you might find elsewhere. But they are ideal if you want to find out more about someone and will lead to some introspective and illuminating conversations.

Getting to the heart of what a person is all about has never been easier with these questions!

Personal Questions To Ask List

These questions are perfect if you want to find out more about somebody and can be asked to close friends or people you’ve just met.

Similar to questions that will help you to get to know someone, some of these questions might be too personal if you don’t the person that well.

So, choose the questions below that reflect how well you know someone before you ask. Or you could be bold and I’ve straight in. The choice is yours.

1. What’s one area of your life you can improve to become a better person?

2. What’s the achievement of yours that you’re most proud of?

3. If you could start again in a new country, which one would it be?

4. What’s the biggest hurdle you’ve had to overcome to get to where you are today?

5. If you had two weeks to live, what things would you want to do?

6. If you received $1million, what would be the first thing you would do?

7. Do you think it’s possible to get along with someone if you have nothing in common with them?

8. What’s a bad habit you struggle to eliminate from your life?

9. If you had the choice to be born again after you die, would you live your life any differently?

10. What memory from your childhood do you look back upon and think that really helped me become the person I am today?

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11. What’s one thing, no matter how old you get, you’ll never grow out of?

12. Do you find it easy to socialise and get to know new people?

13. Is your current job fulfilling or is it getting in the way of you following your dreams?

14. If I asked your best friend, what would they say are your best and worst traits?

15. Are you someone that walks away from danger or walks towards it?

personal questions to ask walking towards danger

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16. Did your family have a lot of money while you were growing up?

17. Would you rather die young but live a healthy life or die old and have a number of health issues?

18. What’s one thing you’re really good at that most other people struggle with?

19. If you were stuck on a desert island alone awaiting rescue, what would you do to fill your time?

20. If you could meet anyone, whether dead or alive, who would it be and why?

21. If you could remove one weakness from your life and replace it with a strength, what would it be and why?

22. What’s something someone could do to you that you would never forgive them for?

23. When you do something to help another person, do you like receiving praise or are you happy letting it go unnoticed?

24. Is honesty or respect more important in a relationship?

25. Are you hot-headed or do you keep a cool head in most situations?

26. When you feel stressed or overwhelmed with anxiety, what do you do to relax?

27. Where do you sit on the political spectrum?

28. If you could relive one period from your life, which one would it be?

29. Is there currently anyone in your life that you feel adds nothing and stops you from becoming the person you want to be?

30. How did you meet your partner?

personal questions to ask how you met your partner

Next: Deep conversation starters

31. Have you ever stolen anything?

32. If money was no issue, where would you most like to travel to?

33. Where would you like to be in 10 years?

34. What do you currently do to get stability and comfort in your life?

35. What personal values do you live by?

36. If it was legal in the country where you live, would you own a firearm?

37. What part of your daily routine do you enjoy the most?

38. Is there anything you wished you’d asked your loved one’s before they passed away?

39. Do you believe humanity has a future on this planet?

40. Have you ever completely lost your cool?

41. What personal possessions could you not live without?

42. What has been the best advice you’ve ever been given?

43. What would be the most likely reason for humans to go extinct?

44. Where could your life be improved?

45. When was the last time you cried?

personal questions to ask last time you cried

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46. When did you last get Dejavu? What happened?

47. Do you have the right work-life balance?

48. Have you ever been in a situation where the bad has overcome the good within you?

49. Is there anyone that you feel you have unfinished business with?

50. What makes you a leader? How do you lead by example?

51. What are your guilty pleasures in life?

52. What bad habits do you have?

53. What healthy habits do you have?

54. Have you ever had to make a life and death decision?

55. What has been the best and worst decision of your life?

56. What are your thoughts on more people turning to a plant-based diet?

57. How was life for you growing up?

58. Are you someone who deals with failure well, or do you take it to heart?

59. What do you do to deal with negative thoughts?

60. Why did your last relationship end?

personal questions to ask relationship ended

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61. Have you ever cheated on someone?

62. What makes you unique and different to others?

63. Do you behave differently around your work colleagues than you do around your partner?

64. Do you worry that social media companies and the government spy on us to gain information?

65. What’s your morning routine after you wake up?

66. Do you enjoy speaking to people through emails/texts or over the phone?

67. How much do you want to achieve in life, and what do you want to achieve?

68. At the end of your life, do you think death will come easy?

69. Have you ever experienced something you couldn’t explain?

70. What motivates you every morning when you get out of bed?

71. What do your family think about your life choices?

72. Have you ever been in trouble with the law?

73. What would you do if you realised that you were in a relationship with someone who was not good for you as a person?

74. What book, TV series or film most resembles your life?

75. Is money important to you? Do you think you can be happy without it?

personal questions to ask is money important

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76. Would you ever move away from friends and family for work?

77. Do you think modern technology helps or damages our lives?

78. Are you good at keeping in contact with people you haven’t seen for a while?

79. How well do you react to your mistakes? Do you always admit when you’ve made a mistake?

80. What’s your favourite famous quote? Do you have your own quote about life?

81. What do you first notice when you meet someone new?

82. What’s your secret place you like to retreat to when life gets stressful?

83. What part of the world would you like to settle in?

84. What’s the biggest stumbling block currently that’s stopping you from achieving what you want?

85. Were you present at the birth of your child?

86. What has been your best birthday so far?

87. What qualities keep a family strong and there for each other?

88. Do you think that girls have an easier life than guys?

89. What do you think about your generation?

90. Would you say you were a feminist?

personal questions to ask feminist

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91. What instantly makes you happy?

92. What was your first impression of your current partner?

93. Have you ever completely misjudged someone, and they were not who you thought they were?

94. Have you ever been shocked by someone’s actions?

95. What would the people you love say at your funeral?

96. Would you say you are a patriotic person?

97. Have you ever had an operation?

98. What in your eyes is the worst thing someone can do that isn’t currently illegal?

99. What movie did you really connect with?

100. When was the last time that you completely lost it?

101. Do you embrace change or run away from it?

102. What song relates to your life?

103. What’s the strangest nickname someone has ever given you?

104. What’s the most personal question you’ve ever been asked?

105. Do you ever find it difficult to be honest, because what you say may hurt other people?

personal questions to ask hurting someone

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106. Are you jealous of anyone?

107. Do you dislike the thought of someone else at work being better than you?

108. Do you ever show the real you, or do you often pretend to be someone your not?

109. Are you ambitious?

110. What do people instantly think of you when they meet you?

111. Do you look up to anyone famous?

112. Do you think Karma is a real thing? Do you think that people always get what’s coming to them?

113. What has been your greatest regret in life so far?

114. Would you rather end world poverty or end all world current and future conflicts?

115. Is your life now as you expected it would be?

116. Would you rather be extremely happy in life but very poor or extremely rich and very unhappy?

117. Has there ever been an occasion where you’ve said what you were thinking out loud?

118. What has been the biggest self-realisation you’ve had?

119. What thoughts keep you up at night?

120. What drives you crazy about other people?

Looking For More Questions?

Rapid fire questions – A collection of questions you can ask in quick succession to get to know somebody.

Embarrassing questions – If you want to make your friends squirm, these are the questions to ask!

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.