102 Psychological Questions That Reveal Someone’s True Personality

In the quest to understand the human psyche, psychologists have long utilized questions to uncover layers of people’s personalities. In fact, there are certain questions you can ask that can reveal much deeper meanings if you’re willing to look beyond the surface. They can offer a glimpse into someone’s motivations, fears, and desires, and ultimately tell you a lot more about who they are at their core. This fosters a greater level of understanding and ultimately helps you feel more connected.

If you’re embarking on a new relationship or aiming to deepen an existing one, romantic or otherwise, here are some psychological questions you might consider posing to uncover the truth of who they are.

  1. What’s a childhood memory that makes you smile?
  2. How do you handle stress or pressure?
  3. What does your ideal day look like?
  4. How do you define success?
  5. Are you more driven by the process or the result?
  6. What’s the most challenging thing you’ve ever done?
  7. What’s a talent or hobby you have that not many people know about?
  8. How do you deal with conflict?
  9. Describe a time you took a risk. What did you learn?
  10. How do you prioritize your tasks or responsibilities?
  11. What’s something you’re really proud of but never have an excuse to talk about?
  12. What are your core values?
  13. Do you believe in fate or free will? Why?
  14. How do you approach change?
  15. What kind of role does empathy play in your life?
  16. What makes you feel fulfilled?
  17. How do you react when things don’t go your way?
  18. What’s a book, movie, or song that has deeply affected you?
  19. How do you recharge?
  20. How do you define a good friend?
  21. What’s a personal challenge you’re currently trying to overcome?
  22. What do you want to be remembered for?
  23. How do you show love to others?
  24. What are you most afraid of?
  25. What motivates you to get up every morning?
  26. How do you handle criticism?
  27. What’s a lesson you had to learn the hard way?
  28. What do you consider your greatest strength? Weakness?
  29. How do you set boundaries in your personal and professional life?
  30. What’s something you’ve always wanted to learn or do?
  31. How do you feel about the concept of work-life balance?
  32. What’s a cause or issue you’re passionate about?
  33. How do you deal with regrets?
  34. What role does gratitude play in your life?
  35. How do you approach giving and receiving feedback?
  36. How do you know when to keep trying and when to let go?
  37. What’s an experience that has made you a stronger person?
  38. How do you handle the unknown or uncertain situations?
  39. What does “happiness” mean to you?
  40. Describe a time when you had to step out of your comfort zone.
  41. What qualities do you admire in others?
  42. What’s something you believe in that not everyone agrees with?
  43. How do you define and pursue authenticity?
  44. What’s a piece of advice you’ve received that has stuck with you?
  45. How do you handle setbacks or failures?
  46. Do you consider yourself more of a thinker or a doer?
  47. What’s the biggest lesson life has taught you so far?
  48. How do you determine trustworthiness in someone?
  49. How do you handle envy or jealousy?
  50. How do you define personal growth, and how do you pursue it?
  51. What did you want to be when you were a kid?

More psychological personality questions that offer insight into someone

  1. How do you handle disappointment?
  2. What do you believe is the purpose of life?
  3. If you could send a message to your younger self, what would it be?
  4. What are three things on your bucket list?
  5. Who has been the most influential person in your life?
  6. How do you define beauty?
  7. What’s a recurring dream or nightmare you’ve had?
  8. How do you handle rejection?
  9. What’s your philosophy on love?
  10. How do you confront your fears?
  11. What’s something you’ve changed your mind about in the last year?
  12. How do you spend your free time?
  13. What do you think is the meaning of life?
  14. How do you handle loneliness?
  15. Do you believe in second chances? Why or why not?
  16. How important is self-awareness to you?
  17. What do you consider a wasted life?
  18. How do you cope with loss?
  19. What’s a belief you hold strongly, even if others might disagree?
  20. How do you handle guilt?
  21. What’s something you’ve forgiven yourself for?
  22. Are you more influenced by logic or emotions?
  23. How do you seek validation: internally, externally, or a combination of both?
  24. What’s a promise you’ve made and intend to keep?
  25. How do you perceive time: as a straight line, a cycle, or something else?
  26. What’s an event that drastically changed your perspective?
  27. How do you show compassion?
  28. Do you believe in life after death?
  29. How do you define intimacy?
  30. How important is personal space to you?
  31. How do you face adversity?
  32. What’s something that overwhelms you?
  33. How do you define personal freedom?
  34. What are your thoughts on destiny?
  35. How do you handle anger?
  36. What’s an experience that’s shaped your values?
  37. What’s a challenge you’ve set for yourself?
  38. How do you manage expectations, both your own and others’?
  39. What are your thoughts on vulnerability?
  40. Would you want to know when you were going to die?
  41. What are the qualities of a true leader?
  42. How do you define spirituality?
  43. What’s a risk you regret not taking?
  44. How do you deal with inner conflict?
  45. What role does tradition play in your life?
  46. How do you navigate moral dilemmas?
  47. What’s an assumption people make about you that’s incorrect?
  48. How do you seek clarity in confusion?
  49. How important is legacy to you?
  50. What’s a habit you’re trying to break or cultivate?
  51. How do you measure personal growth?

What to do with this information

Whether it’s a friend or a romantic interest, knowing the answer to these questions can give you a deeper insight into the other person, help you form a deeper connection with the other person, and foster a greater sense of understanding and camaraderie. This also gives you a bit of a blueprint for the ways you interact with them in ways that will make your relationship fulfilling and peaceful.

Gail is Bolde's social media and partnership manager, as well as an all-around behind-the-scenes renaissance woman. She worked for more than 25 years in her city's local government before making the switch to women's lifestyle and relationship sites, initially at HelloGiggles before making the switch to Bolde.