100 Questions to Ask Your Boyfriend

There are all kinds of questions to ask your boyfriend while you're in the process of getting to know him. And the process of getting to know him doesn't just last for the first 60 or 90 days of a relationship. It can take years to get to know someone well. We've created a list of 100 questions to ask your boyfriend, organized into lists of "top ten questions to ask your boyfriend" with specific connotations.

Fun Questions to Ask Your Boyfriend When You're Bored

Here are some fun questions to ask your boyfriend the next time you're bored:

1. If you could relive any one day of your life, which day would you choose and why?
2. Who's the most important person in your life?
3. What's the most embarrassing thing that's ever happened to you?
4. If you could go anywhere at all on vacation, leaving tomorrow, where would you go?
5. If you could only use on word to describe yourself, what would it be?
6. If you could change one thing about your past, what would you change?
7. If you could be a character from a movie, which character would you be?
8. Who was your favorite ex-girlfriend?
9. Who is your best female friend? Besides me?
10. What about me do you NOT like?

Personal Questions to Ask Your Boyfriend to Get to Know Him Better

Some of these questions are less personal than others, but there are all part of getting to know him better.

11. What's your favorite color?
12. Do you have brothers and/or sisters?
13. Where did you grow up?
14. Has a girl ever asked you out?
15. Would it bother you if a girl did ask you out?
16. What are your goals in life?
17. Do you believe in God?
18. What kinds of sexual fantasies do you have?
19. What do you think of "open" relationships?
20. What was your 1st impression of me?

Questions to Ask Your Boyfriend to See if He Loves You

If you're not sure whether or not your boyfriend loves you, then there are some questions you could ask him. There are also some questions you should ask yourself.

21. How would you know if I were Miss Right?
22. Would you still love me if I had an accident and had horrible scars?
23. Would you still love me if I were dying from a rare disease?
24. If I moved away, would you wait for me to come back? How long would you wait?
25. If you broke up with me, what would the reason be?
26. If you haven't met his family yet, ask him when you're going to get to meet them. If he's excited and eager about having you meet his family, then that's a good sign. (Although the reverse isn't necessarily true; he might be embarrassed by his family.)
27. Question to ask yourself: Does he call me on the phone often? Men who call on the phone a lot are more likely to be in love. A lot means at least once a week, but maybe more.
28. Another question to ask yourself: How often does he touch you? Men demonstrate love via touch, and if he touches you often, then that's a good sign.
29. And another question to ask yourself: Does he ask YOU questions about what's going on with you? If not, then he might not be in love with you. He might also be a lout. Hard to tell.
30. One last question to ask yourself: Does he TELL you he loves you?

Serious Questions to Ask Your Boyfriend About Your Relationship

After you've been together a while, it's probably time to ask some serious questions. Some of these need to be asked before certain relationship milestones; those are obvious.

31. Is there anything I need to know before we have sex for the 1st time? (Diseases, etc. If you're having sex, be mature about it and get this out of the way.)
32. Do I do anything that embarrasses you when we're together in public?
33. What would you do if you fell in love with someone else while we're together?
34. Do you want/need to have pets?
35. What kind of financial goals do you have? What's your financial situation currently?
36. Why did you pick me as your girlfriend?
37. Are you bored with our relationship at all?
38. How serious do you think our relationship is?
39. Are there things about our relationship you'd like to change?
40. What kind of code of ethics/morality do you have, if any?

Important Questions to Ask Your Boyfriend Before Marriage

Getting married is a huge commitment. And it's probably not for everyone. But if you're thinking about taking that step, you should know the answers to these important questions before marrying him.

41. What would you do if I cheated on you?
42. Would you ever cheat on me, and if you did, how would you expect me to handle it?
43. Do you expect me to work or stay home and tend to kids?
44. Do you think we should live together first before getting married?
45. How many kids do you want to have?
46. How important is religion in your life?
47. Have you been married before? If so, what happened?
48. How do you think people should handle divorce?
49. Do you want a prenuptial agreement?
50. How much time do you want to spend together after we're married?

Random Questions to Ask Your Boyfriend on the Phone

Maybe he's away on vacation. Or maybe you just like talking to him on the phone. These random questions will serve as conversation starters for the two of you.

51. What kinds of nightmares do you have, if any?
52. What's your favorite fruit and why?
53. What are your favorite tv shows?
54. What are your favorite books?
55. What would you do if you won the lottery?
56. Are you a jealous person?
57. Are you a mommy's boy or a daddy's boy?
58. What was your relationship with your parents like?
59. What was your parents' relationship with each other like?
60. Are you a dog person or a cat person?

Questions to Ask Your Boyfriend to See How Well He Knows You

We always wonder how much attention a guy is paying to us. If your relationship is still fairly new, you might want to ask him some of these questions to get an idea of how well he knows you.

61. What's my favorite meal?
62. What's my second-favorite kind of food?
63. Am I a morning person or a night person?
64. What's my favorite color?
65. Do I believe in God?
66. What kinds of goals do you think I have?
67. What would you say are my 3 most important personality traits?
68. Who's my favorite celebrity?
69. Do I believe in ghosts and/or extraterrestrial life?
70. What do I like to do for fun?

Funny Questions to Ask Your Boyfriend

Almost any question you ask your boyfriend can be funny if you have the right attitude, and if he has a senses of humor. Here are some suggested funny questions to ask your boyfriend.

71. If you could choose a superpower, which would you choose?
72. Would you rather be able to fly or be able to turn invisible?
73. Do you know any good jokes?
74. Can you do any impersonations?
75. What was the worst job you ever had?
76. What's the funniest thing to ever happen to you?
77. Who's your favorite standup comedian?
78. What's your favorite comedy movie?
79. What's your most embarrassing nickname?
80. What did you look like when you were younger?

Good Questions to Ask Your Boyfriend During 20 Questions

20 questions is a classic game where one person thinks of something, and the other person asks yes/no questions to figure out what the object is. The traditional 1st question is "animal, vegetable, or mineral?" Here are some other good questions to ask during 20 quesitons.

81. If it's an animal, ask if it's male or female?
82. Also ask if it's alive or dead.
83. If it's a dead person, ask if it's a person from this century.
84. Is the person famous or not?
85. Try to narrow down why the person is famous with your other questions.
86. Start with broad questions and get more narrow.
87. Is it bigger than a breadbox? (That's a classic.)
88. Is he/she often in the tabloids?
89. Each question should try to cut the number of possible answers roughly in half.
90. You should be able to win at 20 questions every time, if you use a strategy.

If you want to see an artificial intelligence in action winning at 20 questions, check this cool site out: 20q.net.

Awkward Questions to Ask Your Boyfriend

Some awkward questions for your boyfriend need to be asked. Some don't. You get to decide.

91. Do you love me?
92. How much do you love me?
93. Why do you love me?
94. How many girlfriends did you have before me?
95. Are you a virgin?
96. Do you ever plan to get married?
97. Do you ever plan to have children?
98. What would you do if my sister/best friend made a pass at you?
99. Would you ever consider a threesome? Would it matter whether the 3rd were a man or a woman?
100. Will you go shopping with me?

Some of the questions we didn't include on this list, but that you might consider asking anyway, include deep questions to ask your boyfriend, cute questions to ask your boyfriend, interesting questions to ask your boyfriend, etc.