Sometimes it's difficult to start meaningful conversations with your man, but these 45 questions can trigger fun, interesting or insightful discussions (remember to find out the why behind their answer):

  1. What currently makes you feel the most fulfilled?

  2. What event in your life would make a good movie?

  3. What does your ideal life look like?

  4. What are the highest and lowest points of your life?

  5. What are the strongest and weakest parts of our relationship? How can we make the weak parts stronger?

  6. What's holding you back from being the person you want to be?

  7. What terrible movie do you love?

  8. What does honor mean to you? How important is it to you?

  9. What are you passionate about?

  10. What are five things you enjoy doing with me?

  11. If you died today, what regrets would you have?

  12. If you had to become an inanimate object for a year, what object would you choose to be?

  13. Do people have an obligation to help others or should people only be responsible for themselves?

  14. What's the most important object you own?

  15. What's your dream vacation? (Now plan it!)

  16. What's something you find difficult that most people find easy?

  17. If you could only eat one thing for the rest of your life, what would it be?

  18. What are the best and worst parts of human nature?

  19. Who or what is your nemesis?

  20. Write down three things you love the most about your partner. See if they can correctly guess what's on your list.

  21. What three events made the biggest impact on who you are today?

  22. What was your best mic-drop moment?

  23. What's the worst and best thing about being a guy?

  24. What's the biggest doubt you have?

  25. What do I do that drives you crazy?

  26. Do you have any irrational fears?

  27. What high-level job do you think you could lie your way into with no experience and no one would notice?

  28. If you were given an envelope with the the time and date of your death inside, would you open it?

  29. What are you most grateful for in this exact moment?

  30. What do you find annoying about me?

  31. Is there something you would like to change about yourself? How would you do it?

  32. What's the most useless talent you have?

  33. What's the most beneficial emotion? How about the most destructive?

  34. If your family and friends were asked to describe you, who would provide the most accurate description? What do you think they would say?

  35. What is your craziest fantasy?

  36. What's the one thing is that you cannot live without?

  37. What was the worst purchase you've ever made?

  38. What issue do most people think is black and white, but you think there is a lot nuance to?

  39. What do you want to be known for when you die?

  40. What's something you've tried that you'll never, ever try again?

  41. If you had to choose one cause to dedicate your life to, what would that cause be?

  42. What was your most embarrassing moment?

  43. What should be on our couple bucket list?

  44. Are there any laws or social rules that completely baffle you?

  45. What do people rarely understand about you?

Sometimes conversations with people in our lives become more of a routine. There is sometimes a lack of depth and feeling. Take your man and this list out on a date, and put away your phones and other distractions. Spend some time getting to know each other better, share laughs and become more united.


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