109 Meaningful Questions and Tips To Spark Deep Emotional Connections

Everyone has sometimes a hard time leading a deep meaningful conversation and coming up with ways to get to know the person they’re talking to.

I’ve collected the most interesting questions for you, and the list will be updated constantly, so you will never run out of things to say on a date or in your social circle – you could make an evening out of it and get to know your existing friends better over a few glasses of wine.

I advise you to go through them yourself and find great answers in advance.

Make sure you ask only those questions you’re truly excited about and interested to hear the answer. Normally, these questions would be great for in-person conversations but since this is now pretty impossible in the current situation of social distancing they can be handy in the online dating sphere.

Whatever you do with the questions, make sure you actually lead a conversation. You are supposed to relate to the other person as well and not just ask question after question. Relating can mean sharing your thoughts about what they said or showing your perspective about things from your personal experiences. Otherwise, the conversation will feel like an interview and won’t be a good basis for sparking an emotional connection.

And last but not least, one of the most important things for an intriguing conversation is your ability to listen and take your time to respond and relate. When you don’t get stuck in your head, you don’t feel the need to prepare your next question in advance and you can easier navigate the conversation to your strengths. That means if you don’t like a certain topic, you can jump to a related topic you feel more excited to talk about. Moreover, you’ll be enjoying your time being social and connecting with people even under the current circumstances of social isolation.

You can also use the questions for inspiration for topics you’d like to talk about and share your opinion on.

    1. What is the most important thing someone can do to improve themselves? What is the one thing that made you improve the most on a personal level?
    2. What were you most afraid of in your twenties?
    3. Which wallpaper hung on your wall when you were a child?
    4. What was cool when you were young but isn’t cool now?
    5. Have you ever experienced social pressure?
    6. If you can change one thing in society what would it be?
    7. Do you think we have free will?
    8. Do you think Artificial Intelligence will end up benefiting or harming humanity?
    9. What is your best way to attain happiness?
    10. What bridges are you happy you burned?
    11. Who in your life do you wish you’d met sooner?
    12. How much does speaking in another language affect our thinking?
    13. What impression do you think you give when you first meet someone?
    14. If you could start a country from scratch, what would it be like?
    15. What would you do if you knew the world will end in a month?
    16. If you could have any animal as a pet, what animal would you choose?
    17. What questions would you ask to get the most accurate information about who a person truly is?
    18. What are the most interesting things to see in your country?
    19. What makes you most angry about your country?
    20. If you were about to get a tattoo right now, what would it be?
    21. Which languages would you like to be able to speak freely?
    22. How would you describe your job to a 6-year-old? How does someone get into that job?
    23. What’s the most challenging part of your job?
    24. If you could start over again, would you choose the same career? Why?
    25. If you didn’t have any obligations in your daily life, how would you describe your perfect day?
    26. What is your most warming memory?
    27. What’s the silliest thing you’ve convinced someone of?
    28. What topics could you spend hours talking about?
    29. What is the most important lesson life has taught you?
    30. What would you change about the way you were raised?
    31. What is the weirdest thing you believed in as a child?
    32. What do you admire most about your parents?
    33. Do you prefer living near or far from relatives?
    34. What was your biggest fear that you’ve overcome? What fear would you still like to overcome?
    35. What odd smell do you really enjoy?
    36. What is the weirdest thing you have ever eaten?
    37. What’s the one thing that drives you crazy in this world?
    38. Is there any food that grosses you out?
    39. What weird food combinations do you really enjoy?
    40. Have you ever been in love with your best friend?
    41. What was the hardest thing you have ever done?
    42. What’s your worst example of procrastination?
    43. What’s one mistake you keep repeating?
    44. Which recent news story stuck with you the most?
    45. Why do you think there are so many religions in the world?
    46. Describe a fun date that only costs $20.
    47. What do you hate most about first dates?
    48. What are your most important rules when going on a date?
    49. Is there something that you’ve dreamt of doing for a long time? Why haven’t you done it?
    50. What’s your “and then it got worse” story?
    51. What is your biggest goal in life?
    52. What kind of real-life people inspire you?
    53. What memory instantly makes you smile?
    54. If you had to choose one activity that you had to do every single day for the rest of your life, what would it be?
    55. Do you have any scars? How did you get them?
    56. What has caused you the most emotional pain in your life?
    57. Have you ever believed in God?
    58. What do you do when you can’t fall asleep?
    59. What do you value most in a friendship?
    60. What achievement of yours are you most proud of?
    61. What do you like and hate about yourself?
    62. What are some strange beliefs that you still have?
    63. What’s the strangest dream you’ve ever had?
    64. What’s the coolest animal you’ve seen in the wild?
    65. What role does money play in your life?
    66. What do you feel most grateful for?
    67. What are you doing with pleasure, that others don’t enjoy at all?
    68. Who is your role model/mentor? What qualities make them your choice? What did you learn from them?
    69. What is the greatest accomplishment of your life?
    70. What was the toughest period in your life?
    71. What’s something that should be taught in school that isn’t?
    72. What do you do to improve your mood when you are in a bad mood?
    73. If you could wake up tomorrow having gained any one quality or ability, what would it be?
    74. What do you usually do when you wake up on a free day?
    75. If you could sit down with your 15-year old self, what would you tell him or her?
    76. What turns you on most?
    77. What was the craziest sex dream you’ve had?
    78. What is an experience that the opposite sex can have and you can’t, but that you would like to make?
    79. When did you last cry in front of another person?
    80. What is the closest you ever got to be famous? Would you like to be famous?
    81. If you could change one thing about the way you look, what would it be?
    82. What’s your funniest “drunk” story?
    83. What was the most embarrassing moment in your life so far?
    84. Have you ever experienced something paranormal?
    85. What is your craziest dating story?
    86. What is the most romantic thing someone has done for you?
    87. What was the weirdest sexual experience you ever had?
    88. Where would you go if you could teleport anywhere in the world?
    89. Which book are you ashamed to admit you love?
    90. What do you think about the influence of social media on us?
    91. If you ruled the world, what would you change?
    92. What’s the most amazing place in nature you’ve seen?
    93. What are some personal experiences that have changed your perspective about life?
    94. If you could go back or forth in time but never come back, what would you do?
    95. If you had $30 million in the bank, what would you be doing differently?
    96. If someone could tell you the truth about the future, what would you want to know?
    97. How different was your life one year ago?
    98. What’s the game you’ve been most addicted to?
    99. If you could create a virtual reality world you could live in, what would it look like?
    100. How do you think the world will change in 50 years?
    101. Given the choice of anyone in the world, alive or dead whom would you want to have a meaningful conversation with
    102. If you knew that in one year you died suddenly, would you change anything about the way you are living now?
    103. If you wake up one year from now and your life is the same as today, would you regret it?
    104. If you were to disappear today with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
    105. If you could choose a superpower, what would it be and why?
    106. What would you choose to eat if you had to eat it every day for the rest of your life?
    107. If you could master any instrument, what would it be?
    108. If you could be a character from a tv-show, who would you choose to be?
    109. What talent would you like to have?