101 Questions To Ask Your Boyfriend

Relationships can be a complex and sometimes, its hard to know if you’re with the right person.  Even if you get along well, you might have some basic differences in opinions or goals that can turn into conflict later on.

The following are a group of 101 questions to ask your boyfriend that are different from the many other questions posted on this blog and on our previous post: “Questions To Ask Your Boyfriend“.

101 Questions To Ask Your Boyfriend



1. Are you looking for a long term relationship?
2. How do you feel about ex relationships?
3. How do you feel about kids?
4. If you want kids, how many do you want?
5. Should one person in a relationship stay at home with the kids?
6. Does it matter who it is?
7. How do you feel about your family?
8. How do you feel about your partner’s family?
9. Are you religious?
10. Do you go to church?
11. Does your partner need to go with you?
12. How do you feel about people with beliefs that differ from yours?
13. How do you feel about birth control?
14. Whose responsibility is it?
15. How do you show you love your partner?
16. How should your partner show they love you?
17. How do you react when your partner does something that ticks you off?
18. Is cheating ever okay?
19. Is it ever okay to lie to or deceive your partner?
20. Do you ever want to get married?


21. Would you want a big wedding or a small one?
22. What’s your perfect honeymoon?
23. Are there any groups of people you just can’t stand?
24. Are there any people you think are just better than others?
25. Do you like pets?
26. Do you think it’s okay to tell your partner what to do/wear/say?
27. Do you have strong political opinions?
28. Should both people in a relationship agree on everything?
29. Do you prefer to sleep together, or alone?
30. Should a couple share a room, or should each person have his or her own space?
31. Do you get jealous?
32. Who do you get jealous of?
33. What do you do about it?
34. Is it okay for your partner to have girl friends?
35. How about same guy friends?
36. How much time should couples spend together?
37. Do you ever feel like your partners are too clingy?
38. Do you ever feel as though your partners are too distant?
39. Which comes first, work or a relationship?
40. How much money do you need to be happy?


41. Do you prefer to share finances with your partner, or keep them separate?
42. How do you feel about sex outside of marriage?
43. Is there anything we can do in bed that you think is just wrong?
44. What’s your sex drive like?
45. Any kinks I should know about?
46. Are looks important in someone you’re dating?
47. If I got fat, would you dump me?
48. What if I lost a lot of weight?
49. Who are your exes and why’d you break up?
50. What makes a relationship a success?
51. How about what makes one a failure?
52. Is money important?
53. Do you respect women?
54. How about men?
55. Are there any big, innate differences between the sexes?
56. Ever had your heart broken?
57. Do you still have feelings for your exes?
58. What would you do if one of them asked you back?
59. What was your longest previous relationship?
60. What kind of movies do you like?


61. What’s your favorite thing to do on the weekends?
62. Exercise – fun or a drag?
63. How about the great outdoors?
64. Do you smoke?
65. How do you feel when other people smoke?
66. Do you eat meat?
67. Do you have strong feelings about animals?
68. Are you a political activist?
69. Do you keep kosher/halal/have dietary restrictions?
70. Do you like to read?
71. Do you like to learn?
72. What’s your worst habit?
73. What would you rather change about yourself?
74. What do you wish you could change about me?
75. What do you like best about me?
76. What do you like best about yourself?
77. Should couples spend time apart?
78. Should couples have all the same hobbies?
79. Do you keep secrets from your lovers?
80. What kind of secrets are ok?


81. What would you do if I were in a disfiguring accident?
82. A disabling one?
83. What are you allergic to?
84. Do you have any major medical conditions I should know about?
85. How about phobias?
86. What are your career goals?
87. Do you move a lot?
88. Do you expect to keep on moving?
89. Which is better, the country, the city or the suburbs?
90. Where did you grow up?
91. Do you like one part of the world/country best?
92. Do you like my friends?
93. Do your friends like me?
94. Are you an introvert or an extrovert?
95. What’s your idea of the perfect date?
96. Should relationships require work?
97. Do you believe in true love?
98. Which is better, thinking or feeling?
99. How do you make decisions?
100. What does love mean to you?
101. Do you love me?

Some of these questions are serious and some not.  However, all of them have the potential to change a relationship for better or worse.  From little things like what movies you like to watch and how do you like to spend a Friday night. To the big things like kids, a career and religion. Knowing a lot about your boyfriend can help you decide if you’re right for each other and it will also help you see the compromises that can or can not be made.

If you’re in a relationship and you are not sure about it, maybe you need to ask some of the above questions.  Don’t ask them all at once – your boyfriend will just feel like he’s being interrogated.  Instead, go through this list and think about whether you know the answer to these 101 questions. The more you know about each other, the better your chances are of finding out whether your relationship is going to last.

Get your free copy of the 100 Questions Before Marriage sample eBook and for more questions to ask your boyfriend, feel free to instantly download your copy of 1000 Questions For Couples today!

Click here to instantly download your copy of 1000 Questions for Couples now!

One Response to “101 Questions To Ask Your Boyfriend”

  1. 34E Says:

    I know all of these answers about every boyfriend I was ever with for more than 6 months. If these topics do not come up naturally in deep conversation you are not comfortable enough with each other to get engaged, no way no how.

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