Most men aren’t exactly open books. You can be married to a man for decades and still have a hard time getting him to lock down on a favorite color. He may tell you about the girl who cheated on him, but do you know how he reacted to the end of that relationship? And what are your new guy’s goals… if he has any? When he says he wants a committed relationship, what does he really mean? Sometimes we’re great at projecting our feelings and aspirations onto our significant others, without really noticing that they want something different (or nothing at all).
If you’re a chatty girl, you’re probably with a guy who enjoys listening to you. That means you’ve probably mostly heard him chime in when he agrees with one of your big ideas. Especially if you haven’t known each other long, he might not be very comfortable contradicting you. “I want a house with a lot of land and quiet” might be met with, “Quiet is nice. I hate my apartment in the city.” But, he might be thinking about how he absolutely wouldn’t want to mow more than a quarter acre.
So, how do you get a guy (or anyone) to talk? For starters, you start listening. It also helps to ask him questions. These 41 questions might give you some more insight into your new bae. They’re linked to even more lists of questions and include related inquiries to help you further your conversation.
1. If you inherited a billion dollars, what would you do with your life?
2. What’s your most hated chore?
3. What’s something you always procrastinate on?
4. How do you like to spend your days off or what’s your idea of a perfect vacation?
So, on vacation are you more of a “do nothing” or a “do everything” kind of tourist?
5. Do you like kids and want kids?
6. What was your childhood like?
Expand with questions like: Did you take vacations? How did your parents discipline you?
7. What do you want to do with your life? What is your five-year or 10-year plan?
8. What do you hope your life looks like right before you die?
9. Do you have any expectations for yourself?
What are you hardest on yourself for when you mess up? What do you expect from others?
10. What’s the worst thing you’ve ever done? Did you tell anyone? Did you apologize? Have you done anything to make it right or clear your conscience?
11. How important is religion to you? What about your parents? How do you feel about other people’s take on religion?
12. What’s one thing you’ve never been good at?
Did you want to get better? What haven’t you tried, but hope to master someday?
13. What does the perfect relationship look like?
Is it marriage? Does that matter? Do people contribute equally on a financial level? Domestic level?
14. Who is your best friend? Why?
15. Who is the most called/texted person in your contacts?
What do you talk about? How long are you usually conversing?
16. What’s the most difficult thing you’ve ever been through?
17. What’s your most useless “skill?”
If he says algebra, M.A.R.R.Y. H.I.M. — your future tenth grader will thank you.
18. What’s the biggest purchase you ever made?
What about the worst or best? What’s the last thing you charged on your credit card? Will you pay it right off or will it probably sit there for a while?
19. What’s something you were recently super proud about?
20. Who will you always make time for? Why is that person most significant? Is there anyone else? What activity do you always take the time to do?
21. Do you prefer the indoors or outdoors? Why?
22. What are your favorite books/movies?
23. What do you listen to on your commute?
24. What’s your dream job?
25. Is there a chore you think you’re awesome at or enjoy doing?
26. What would your perfect morning look like?
This is another one that says a lot about your compatibility. If you hate mornings and he’s up early and finished with chores by 10a, it could cause strife.
27. What’s your most used app on your phone?
28. What are three things you always have in your fridge?
29. What do you hope someone says about you at your funeral? What songs do you hope they play?
This is both serious and silly. The answers will help you understand his values and goals.
30. What color would you never, ever paint a room in your home? What about the outside of your house?
31. Do you want to have children? If so, how many?
32. If you do want to have children, what do you see as the role the mother plays and the father plays as far as child care duties during infancy and on?
33. How do you view the household division of labor? And what do you base it on?
34. What are your thoughts on financially supporting elderly or sick parents?
35. On a scale of 1 to 10 how important or unimportant is paying off debt to you?
36. What are your thoughts on a prenup if marriage was on the table?
37. What are your feelings on your partner having close friends of the opposite gender?
38. How much input do you think parents should have on your relationships?
39. What are your thoughts on couples taking separate vacations?
40. Do you believe couples should have separate bank accounts? What about once you’re married?
41. Do you feel a partner should tell you about their weekly or monthly expenses?
42. Who do you think should wake up with the baby in the middle of the night?
43. What are your thoughts on couples or marriage counseling?
44. What are your plans for retirement planning?
45. How far ahead in life do you make plans?
46. What’s the biggest doubt you have?
47. What’s something about you that most people get wrong?
48. What movie could you watch on repeat?
49. What is society doing now that everyone will laugh at in 20 years?
50. What’s one thing you’ve done to make the world a better place?
51. How many times have you been in love?
52. Have you ever had a near-death experience?
53. What’s the worst gift you’ve ever gotten?
54. What was the best?
55. If your life was a video game, what would it be?
56. What is one thing that brings a smile to your face, no matter the time of day?
57. What makes you laugh?
58. When you’re feeling super lazy, what’s your guilty-pleasure Netflix show?
59. What’s the scariest thing you’ve ever done?
60. What’s the best thing about your life right now?
61. Can you tell me one thing, big or small, that you’ve never told anyone else?
62. If you were forced to leave your home and move to a county you’ve never been before, what are three things that you’d take with you?
63. What’s a favorite memory with a pet/animal?
64. If tomorrow was your last day on earth, what would you do in your last 24 hours?
65. What’s one thing people would never know about you just by looking at you?
66. Who has completely lost your respect?
67. What movie do you wish life was more like?
68. How many phones have you broken or lost?
69. Who or what is your nemesis?
70. What childish thing do you still enjoy?
71. What’s the worst and best thing about being male?
72. What would you NOT do for 5 million dollars?
73. What long shot have you taken that really paid off?
74. If you could learn only one magic spell, but it could only do something mundane and boring, what would the spell do?
75. You wake up suddenly in the middle of the night. What would be the scariest sound to hear after waking up?
76. What has been your best mic-drop moment so far in life?
77. What are you completely tired of hearing about?
78. Who is someone who made a huge impression on you but you only knew a short time?
79. What field would you consider yourself an expert in?
80. Who is your favorite author? What book did you love most of theirs?
81. What is a habit you want to drop?
82. What is a habit you want to pick up?
83. Do you have a vice, and what is it?
84. What is one memory from your childhood that makes you cringe?
85. What is one memory from your adulthood that makes you cringe?
86. What experience do you want to recreate?
87. What have you learned from your exes or past relationships about yourself?
88. What qualities from your ex do you want to find in future partners?
89. What is your relationship like with your former lovers?
90. How important is monogamy to you?
91. If you were a superhero, what kind of secret identity would you have?
92. Have you ever dated someone your family hated?
93. What’s the worst injury you’ve ever had?
94. What’s the scariest dream you’ve ever had?
95. Are you a spender or a saver?
96. What is something you thought was silly until you tried it?
97. If you had to choose, which Kardashian is your favorite and why?
98. What’s your favorite holiday tradition?
99. What do you always daydream about when you space out?
100. What’s the one thing you hope your mom never finds out about you?
101. Who is your role model?
102. What do you find the most attractive about a woman?
103. Do you find it easy to apologize?
Some of these might sound exceptionally deep while others seem to only scratch the surface. The idea isn’t to stop at just this question but for the question to trigger a conversation. If what he’s most recently proud of is paying off a big credit card from his college years, that tells you a lot about his commitment and maturity.
Of course, there’s certainly nothing wrong with having hobbies and finding ways to unwind. But, if his most recent accomplishment is a great score at the golf course, where he’s played two rounds every weekend all spring and summer for the last three years? Well… The point is, even the superficial stuff can lead to longer conversations and deeper insight. The gist: Never stop asking questions, no matter how long you’ve been together.
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