107 Questions To Ask Your Boyfriend When It’s Getting Serious

Relationships are based on communication. But sometimes that vague sentence isn’t very helpful! Everyone talks about how important it is to communicate but they don’t talk about what you need to communicate about. So as someone in a serious relationship of over 5 years I wanted to share some of the important questions you need to ask while communicating. So keep reading for 107 questions to ask your boyfriend when it’s getting serious.

Note: these questions are intended primarily for asking while still in the dating phase before engagement or marriage. This is because I have not gotten engaged or married yet and don’t believe on speaking about things I don’t have experience in!

So let’s get into these helpful relationship questions to ask your boyfriend (or girlfriend!).

107 questions to ask your boyfriend when it's getting serious!

107 Questions To Ask Your Boyfriend When It’s Getting Serious:

  1. Where do you picture yourself in 5 years?
  2. How do you like to handle conflict?
  3. What is something you would like to change about yourself?
  4. How do you honestly think we can improve our relationship
  5. What is a situation we could have handled better?
  6. What is a disagreement that you believe we handled well?
  7. What is a healthy way for each of us to handle anger?
  8. Name a situation in which I disappointed you?
  9. What is the number 1 thing you think I could do to improve our relationship?
  10. What is the number 1 thing you think you could do to improve our relationship?
  11. What are boundaries you want to draw with family members?
  12. How do you think we should establish boundaries?
  13. What was a time you felt the most connected to me?
  14. How can we connect better in the future?
  15. What does your commitment to me look like?
  16. How can I better express my commitment to you?
  17. What does a committed future look like for us?
  18. What was our most romantic date so far?
  19. What does your dream romantic date look like?
  20. What first attracted you to me?
  21. How can I keep that passion alive?
  22. How can you keep that passion alive?
  23. Describe the attributes that make me a dream partner?
  24. Describe the attributes that you believe make you my dream partner?
  25. How can I provide you with support during hard times?
  26. How will you provide me with support during hard times?
  27. Do you believe in marriage?
  28. If so, what is your dream timeline for marriage?
  29. Do you envision me being the person you marry?
  30. What is something you won’t give up in a marriage?
  31. Is there anything you would want me to give up in a marriage?
  32. Are you willing to commit to a “date schedule” now or in the future?
  33. Do you want to have children?
  34. If so, how many children would you like to have?
  35. Describe your parenting style?
  36. How do you want to discipline children?
  37. What lessons are the most important for you to teach children?
  38. Would you be willing to adopt or surrogate if there is fertility issues?
  39. How would you like to divide child raising responsibilities?
  40. How do you expect to divide holidays between families?
  41. What roles would you like family members to play with future children?
  42. What did you like and not like about your parents parenting style?
  43. Do you have any concerns about my parents parenting style?
  44. What worked well in your past relationships?
  45. What didn’t work in your past relationships?
  46. Have you ever been cheated on?
  47. What is your definition of cheating?
  48. What is your love language?
  49. How can you work with my love language?
  50. What is your favorite thing to do during free time?
  51. What hobby would you like us to start doing together?
  52. Do you need me time, and how much?
  53. If I need me time, how will you respond to that?
  54. Where do you want to live?
  55. How important is it to you to live in a house?
  56. Is the size of a house or location more important to you?
  57. Would you be willing to rent or get a smaller house while saving for a house?
  58. If I got the opportunity would you be willing to move across the country?
  59. If we moved to a city where we didn’t know anyone how would we handle it?
  60. If money wasn’t an object where would you want to live?
  61. What are your dream vacations for the future?
  62. How much of a priority is vacations to you?
  63. Do you want to vacation alone or with friends or family?
  64. Do you have a financial plan for retirement?
  65. What do you want to do during retirement?
  66. What causes have you volunteered for?
  67. If you started a charity today what would it be for?
  68. Do you want any pets (or any more)?
  69. What do you judge about yourself the most?
  70. What do you judge the most about me?
  71. What do you overestimate or underestimate the most about yourself?
  72. What do you overestimate or underestimate the most about me?
  73. What is your current financial situation?
  74. Are you comfortable with your current finances?
  75. Are you comfortable with my current financial situations?
  76. Do you have debt of any sort?
  77. If I have debt, what are your thoughts on handling it?
  78. Do you spend more or save more?
  79. What are your thoughts on combining finances upon marriage?
  80. Do you believe in/want a prenup?
  81. What are your thoughts if I want a prenup?
  82. How should we budget together if finances are combined?
  83. How should we ideally handle large purchases in the future?
  84. Do you have any financial obligations from other marriages or children?
  85. Who will handle the logistics of paying bills?
  86. How will we plan for our children’s financial future (like college)?
  87. What does your ideal day off look like?
  88. Do you prefer to relax when you’re off or go on adventures?
  89. What if I prefer the opposite, how would you handle that?
  90. Would you rather do household chores after work or on weekends?
  91. How will we divide up household chores?
  92. What are your standards for cleanliness?
  93. Are you willing to do more if my standards for cleanliness are higher?
  94. How will we divide cooking?
  95. Would you rather pay someone to fix/update things or do it yourself?
  96. What about hiring help for cleaning?
  97. What makes you feel appreciated?
  98. How can you make me feel appreciated?
  99. How much do you prioritize friendships?
  100. Do you have concerns about any of my friends?
  101. If I have a concern about a friend of yours how will you handle that?
  102. What scares you the most in live?
  103. Describe your dream day in 10 years from now?
  104. What can we do to make that dream day possible?
  105. How can I show you more love daily?
  106. How will you show me more love daily?
  107. What is your favorite thing about our future?
107 important questions to ask in a relationship!

Remember- not every question will be applicable to your relationship but having great communication with your significant other is important! So start asking these questions to your boyfriend or girlfriend when you get serious to help better your communication and truly get to know each other.

Korra The Explorer

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