Questions to Spark Authenticity

Cut through the BS and quickly establish connectedness, intimacy, & trust

Steve Dean
Dec 2, 2014 · 9 min read

How are you?
Where do you work?
What do you drive?

I really hate superficial conversations. Hearing them at networking events makes me cringe. Hearing them on a first date is a total dealbreaker. It’s precisely because of these types of mundane, surface-level questions that networking and dating can feel like a total chore instead of being an opportunity to glimpse into the life of someone new, learn where your paths may have crossed, and discover how your life trajectories may one day converge.

Luckily, there are questions out that that are designed to help us dive beneath the surface extremely quickly. Certain questions give us the power to form stronger connections, be more authentic, break down barriers to intimacy, and save us once and for all from the frustration of an unceremonious “what do you do?”

Here are the top 100 questions to spark authenticity.

Cherish them forever. Use your favorites whenever you can.

  1. What are you most afraid to desire?
    2. Why do you do what you do?
    3. Where do you find yourself most vulnerable?
    4. What is your deepest shame?
    5. What do you do that is not socially acceptable?
    6. What is one experience you’ve had that you don’t believe anyone else has ever experienced before?
    7. What is a belief you would be willing to die for?
    8. What would it look like if you peeled away your mask?
    9. What would be the most difficult decision you’ve ever made?
    10. If today were the last day of your life, would you do what you are about to do today? If not, what would you do instead?
    11. What is something you would happily fail at?
    12. When do you feel you can surrender yourself completely?
    13. What worries you most about the future?
    14. What are you holding onto that you need to let go of?
    15. What is your self-talk like?
    16. What is the biggest mistake you have ever made?
    17. Why do you matter?
    18. Are you happy with yourself?
    19. What is the time when you were most afraid? Heartbroken? Lonely?
    20. What is something that you pretend to understand when you really don’t?
    21. What’s the number one change you need to make in your life in the next twelve months?
    22. When did you not speak up when you should have?
    23. In what way are you your own worst enemy?
    24. What life do you think you are worth?
    25. What do you wish you didn’t know?
    26. What have you given up on?
    27. What mistake do you make over and over again?
    28. What is the biggest thing that has been draining your happiness?
    29. What has your inner voice been telling you lately?
    30. What is worse than death to you?
    31. What do you hate being judged for?
    32. What do you wish you could erase from the past?
    33. When was a time where you took someone for granted and you wish you hadn’t?
    34. In what way are you stronger than you look?
    35. What do people thank you for most often?
    36. What is always worth the wait?
    37. What makes your life worth living?
    38. What do you love most about your life?
    39. In what way do you need a second chance?
    40. What in life frustrates you the most?
    41. What is the best piece of advice you’ve ever gotten?
    42. In what way are you above average?
    43. What kind of love do you believe you deserve?
    44. How do you show someone you love them?
    45. How do you define love?
    46. How do you define poverty?
    47. How do you define illness?
    48. What is the biggest lie you have told yourself?
    49. What is the biggest lie you have ever told someone?
    50. If you had $100 million in the bank, what would your day look like?
    51. What kind of negativity do you struggle to defend yourself against?
    52. What helps you persevere when you feel like giving up?
    53. What is a belief that has slowed you down and held you back in life?
    54. Describe a situation that had been stealing your happiness.
    55. What would you most like to forgive, but can’t allow yourself to?
    56. Where is the one place in the world that you like to escape to?
    57. What is your response to someone says they hate you?
    58. What do you wish people could understand about you?
    59. What do you most apologize for?
    60. What are you dealing with right now?
    61. How would you define loneliness?
    62. What seems the most real to you?
    63. What is one thing that is unique and true about you?
    64. What is the biggest risk you have ever taken in your life?
    65. What gives you a reason to smile?
    66. What is something your mom once said that you will never forget?
    67. What should you never do to yourself?
    68. What is something interesting about you that almost no one knows?
    69. What are you most proud of yourself for?
    70. What is the best compliment someone can give you?
    71. What is the most valuable thing you have ever lost?
    72. When do you think about what you are thinking about?
    73. What could you always use more of?
    74. What do you wish you did sooner?
    75. What are you most afraid to talk about? Why?
    76. What disappoints you the most about life?
    77. What is your back-up plan if the unthinkable happens?
    78. If you were only allowed to keep one memory with you for the rest of your life, what would it be?
    79. What’s something that you’re glad you’ll never have to do again?
    80. When do you lose yourself in what you are doing?
    81. What is one thing that changes people?
    82. What would your version of hell look like?
    83. What would your version of heaven look like?
    84. What has been the worst struggle in your life?
    85. What does your inner child want?
    86. What is something you would love to do so much that you would be okay with failing at.
    87. What are you uncertain about?
    88. What are your best techniques for making someone smile?
    89. What is the nicest thing you have done for a complete stranger?
    90. Where are you playing small in your life right now?
    91. What is something where you have a hard time asking for help?
    92. How did you feel the last time you were completely alone?
    93. What made you cry last?
    94. Where in the world are you the happiest?
    95. Where in the world are you the saddest?
    96. When have you physically/emotionally felt weak?
    97. Do you feel that you have already reached your peak?
    98. What are you doing when you feel most alive?
    99. Who are you surrounded by when you feel most at peace?
    100. What can make you laugh so hard you cry?

Bonus! Questions for Romantic Bonding

I stumbled upon a fascinating article about questions you can use to instantly bond with a romantic partner. Here’s an excerpt from the article, followed by the questions!

Is there a shortcut to bonding with a romantic partner on a deeper level?

From Sam Gosling’s book, Snoop: What Your Stuff Says About You:

Arthur Aron, a psychologist at the State University of New York at Stony Brook, is interested in how people form romantic relationships, and he’s come up with an ingenious way of taking men and women who have never met before and making them feel close to one another. Given that he has just an hour or so to create the intimacy levels that typically take week, months, or years to form, he accelerated the getting-to-know-you process through a set of thirty-six questions crafted to take the participants rapidly from level one in McAdams’s system to level two. The questions are part of an hour-long “sharing game” in which each member of a pair reads a question out loud and then they both answer it before moving on to the next question.

Here are some questions to help you fall in love:

1. Given the choice of anyone in the world, whom would you want as a dinner guest?
2. Would you like to be famous? In what way?
3. Before making a telephone call, do you ever rehearse what you are going to say? Why?
4. What would constitute a “perfect” day for you?
5. When did you last sing to yourself? To someone else?
6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
7. Name three things you and your partner appear to have in common.
8. For what in your life do you feel most grateful?
9. If you could change anything about the way you were raised, what would it be?
10. If you could wake up tomorrow having gained any one quality or ability, what would it be?
11. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
12. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
13. What is the greatest accomplishment of your life?
14. What do you value most in a friendship?
15. What is your most treasured memory?
16. What is your most terrible memory?
17. What does friendship mean to you?
18. What roles do love and affection play in your life?
19. How close and warm is your family? Do you feel your childhood was happier than most other people’s?
20. Complete this sentence:”I wish I had someone with whom I could share…”
21. If you were going to become a close friend with your partner, please share what would be important for him or her to know.
22. Tell your partner what you like about them; be very honest this time saying things that you might not say to someone you’ve just met.
23. Share with your partner an embarrassing moment in your life.
24. When did you last cry in front of another person? By yourself?
25. Tell your partner something that you like about them already.
26. What, if anything, is too serious to be joked about?
27. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

About the Author…

I’m Steve Dean, an NYC-based online dating consultant.

I offer customized consultations to individuals who need help with dating & relationships, as well as dating sites who need help with product strategy and growth.

I like to write and podcast about dating, relationships, and how to get connected to awesome jobs, roommates, and events. If you’d like to keep tabs on what I’m working on, you can follow my Patreon page, or connect with me anywhere:

Patreon | Quora | Twitter | LinkedIn | Instagram


Life at the cutting edge of dating, sex, and relationships

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