Questions To Ask Your Boyfriend

The following are a collected group of questions from previous post made on this blog about different topics that range from intimate, personal, cute, funny, silly, weird, sexual and hard questions that you can ask your boyfriend.

Note: This post is very long. If you don’t have time to read it now, feel free to bookmark it for later. :-)


Questions To Ask Your Boyfriend:

Questions to Ask Your Boyfriend



Taken from post: 100 Questions To Ask Your Boyfriend

1.    Who are your ex girlfriends, (if any) and what made the relationship end as it did?
2.    What have you learned from life that makes you who you are today?
3.    What are your plans (goals) for the future?

Taken from post: 21 Questions To Ask A Guy

4.    If I had an accident and be left with terrible scars for life, would you still love me?
5.    What is it of me that you like the most?
6.    How do you remember your “first love”?
7.    After me, who is your closest female friend? (excluding your mother, and other family members)
8.    How do you remember my first impression?
9.    Would you leave me for a celebrity that really really liked you?
10.    Are you a virgin?
11.    Do you still have feelings for an ex?
12.    What is your best kept intimate secret?
13.    How do you visualize the perfect woman? What are her attributes?
14.    Who was your first girlfriend?
15.    How would you react if I was dating another guy?
16.    At what age do you plan to get married?
17.    What is it that you don’t like about me?
18.    What would be your best reason to break up with me?
19.    How would you react if the doctor told me that I have a deadly disease? Would you still love me?
20.    If I had to move far away for many years, would you wait for me?
21.    If we had a child born with health problems, how would you handle the situation?
22.    What are your financial goals for the future?
23.    How and when would you know if I am the right one?
24.    Do you believe in God? Why?

Taken from post: Fun Questions To Get to Know Someone

25.    Have you ever had the feeling you were being watched?
26.    So, do you really think we evolved from apes? Seriously?
27.    What would you do if you were the last person on this earth?

Taken from post: Intimate Questions To Ask Your Partner

28.    What has been your most intimate experience?
29.    Who has been your most intimate partner?
30.    Do you still have feelings for an ex intimate partner?
31.    How long did your most intimate relationship last?
32.    Do you regret living those intimate experiences with that person?
33.    What made you go that far?
34.    Are you a virgin?
35.    Do you rather follow your heart (that does not think) or your head (that does think)?
36.    What do you think is better: premarital sex or premarital abstinence?
37.    Do you think the past matters in a relationship?
38.    How would you react if I had a more serious intimate relationship in the past?
39.    Do you think it’s OK for me to still have feelings for an ex?
40.    What is your definition of intimate?
41.    Do you agree with: were there was fire, ashes remain?

Taken from post: Random Questions To Ask A Guy

42.    What are your future financial plans?
43.    What is your mayor goal in life?
44.    What is your favorite book?
45.    How would you describe yourself in 3 words?
46.    What are your mayor flaws?
47.    Who is your hero?
48.    What do you consider most important in life?
49.    What would be your questions to ask on a first date?
50.    Do have any type of bad habit?
51.    What is your point of view of the world?
52.    What are your priorities on a first date?
53.    How would you describe the perfect life?
54.    What country would you choose for a honeymoon?Why?
55.    What has been your most embarrassing moment?
56.    What do you do when you are bored?
57.    How do you spend time with your family?
58.    Do you have any enemies? Why?
59.    What has been the most important decisions in your life?
60.    What experiences have marked you the most?
61.    If you could change the past, what would you change?
62.    How do you visualize your future?

The above questionnaire is an example of the type of get to know you questions that can help strengthen a girlfriend/boyfriend relationship. They are also good premarital questions that can be taken into account before marriage.

Some can be considered questions to ask on a first date or questions to ask a potential boyfriend, but they can vary depending on each person, situation and the relationship it self.

But the best use of these questions is to get to know someone better. To help uncover the real and mysterious individual that hides behind the social mask. To see who will be the real person if that boyfriend turns into a husband and a life long spouse.

Within courtship, we only know up to a certain extent about our partner. Within marriage, things change. Both partners will have to learn how to cope with each other with all of their past, present and future for as long as they live.

This would include: family members, friends, neighbors, pets, ex relationships and personal and intimate experiences. The above deep questions for couples help unfold all of this. They are not to be considered a quiz or a survey, but rather simple questioning for better understanding.

As for the answer to these questions, they will depend on his reaction because  they are personal. As mentioned on a previous post, they have to do a lot with the truth, and sometimes, the truth hurts.

For more interesting, romantic and  fun questions to ask your boyfriend, get your copy of  the 100 Questions Before Marriage sample eBook, or Michael Webb’s eBook 1000 Questions For Couples today!

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

94 Responses to “Questions To Ask Your Boyfriend”

  1. Lenny Says:

    You should have called this “Questions that drive guys nuts.”

  2. Dionis Says:

    I know Lenny!
    I am guy my self and I wrote it.

    I’m surprised I did not go crazy =-)

  3. marie Says:

    Hey dude thanks for writing these questions. Gave me something to talk about with my boyfriend. By the way he enjoyed answering them.

  4. Dionis Says:

    Thank you! I am glad that you like them.

  5. Beverly Says:

    Yeah, my boyfriend and I ask each other random questions all the time when we get bored, and sometimes we can’t think of things. I had the notion to google ‘questions to ask your boyfriend’ and I clicked on this. This post really helped me. I love it! Thanks for writing it.

  6. Jenn Says:

    lol Beverly, I found this page the same way!
    Sometimes, there’s so much you want to know, and you just can’t think of specific things to ask… so I agree, helpful post. Thanks heaps.

  7. ha ha my name is beverly too Says:

    i did the same thing

  8. Also a Beverley (spelt diff) Says:

    I also find this via google and it was totally helpful

  9. Dionis Says:

    Wow so many Beverlys!

  10. Kristina Says:

    thx dude these are some narly questions and they helped me get to know my boyfriend really well!! :)

  11. Dionis Says:

    Thanks Kristina. The more questions to ask your boyfriend, the more you get to know your boyfriend.

  12. Sandra Says:

    I like these questions i texted my boyfriend soon to be hubby :]] he said everything right:]]

  13. Ennie Says:

    Thanx dude i loved these hints, so helpful coz the only key to know someone better is through asking questions, sometimes i could fail to know what exactly i wanna know coz i didn’t know what to ask.It has strengthens my relationship.

  14. Dionis Says:

    You’re welcome Ennie. I made these post to help people just like you.

  15. Nina Says:

    This was a great idea. I was fourteen when i met my partner. We are now married with four children and have been together for 14 years. Me and my partener asked these questions to eachother when we started seeing eachother and it was the most interesting, fun and exciting thing to do. Only by asking questions such as these do you know the person and what kind of relationship you are in and also what to expect. Great Idea. You know perfectly what you are talking about. and if the guy or woman goes “nuts” when being asked questions such as these…maybe they aren’t the one for you ;)

  16. Liz Says:

    These questions are so helpful Thank you so much Dionis!! These questions are really unique I went to a few other sites before coming to this and let me just tell you that all the other ones have the same questions and overall they are just nasty questions. These question that u created are really helpful. I never would have even thought about some. :]

  17. Dionis Says:

    Hi Liz,

    Thank you so much. I try my best to keep my content as good as possible for everyone. I try to be unique and different as well.

    As I wrote in my about page when I started this website:

    The content posted on our website display a different point of view of what common Internet sites promote. Our site has a unique touch of what we believe is proper in a male and female relationship.

    I really dedicated time on this post and as you can see, if you put a little bit of passion in anything you do, the results will be positive.

  18. Georgie Says:

    Love these questions, very helpful.

  19. ha! my name isnt beverly! its beth!! Says:

    ya my boyfriend laughed when i asked him these questions.
    it was a fun time :)

  20. Just Samma not beverly. XD Says:

    My boyfirend/bestfriend and I are always playing a game of “20” but after awhile we would start a game and run out of good questions so this’ll keep the game goin!
    Thanks so much!

  21. Kismet Says:

    lol I found I’ve asked my love nearly all of these questions , but thanks for posting :D

  22. kelsey Says:

    i really need a good reply of how i know my boyfriend likes me from ally and kelsey spilman,both 9 and 8 years old

  23. Gunlan Says:

    I loved this girl called Dasiy and then she went with another boy and leave me and she said that she do not went me any more and then i was trying to get her back and she just said that I hate you go away KNOW
    And she was so pretty and I went to her birthday’s has will and I loved her since
    I was small and I can not even belive that she dosen’t like me any more
    and I am publishing this because show her how I feel


  24. Jasmine Says:

    Boyfriend’s getting these questions tonight. He loves answering random questions from me he claims, well see lol.

  25. Dionis Says:

    Hello Kelsey and Ally,

    I recommend giving yourselves some time to get to know who you are first before getting to know another person.
    I see that both of you are very young and the best thing I can say to you as a friend is to learn first, then live.

    – Dionis

  26. Ragan Says:


    Great set of questions you have here. The cool thing is, I was suprised by almost every answer, in a good way. I also loved the fact that these were mostly all judgment questions. By that I mean there was no right or wrong answer. I asked my boyfriend some of these, and I liked hearing his responses. He didn’t always see eye to eye with me, but it made me appreciate him even more that he has his own opinion. We can look at in issue different ways but still respect and love the other person so much for what insight they bring.

    Thanks again :-).

  27. Dionis Says:

    Hi Ragan,

    Thank you so much for your compliment I really appreciate it. I am glad to hear that you love your partner more because of these questions and it because the more knowledge you have about somebody, the more you will come to understand and appreciate them.

    Thanks for the comment!

  28. Ali Says:

    Hey, thanks so much for posting these questions. I have a close guy that knows me too welll and I know alot but just alittle about him at the same time. He loves it when I ask him questions tho. I just couldnt think of any. Know I know him wayyyy better tho!


  29. Bella Says:

    i like this site . i asked my boyfriend what was one thing he didnt like about me, we spent about 1 hour discussing the Question . Thx Lotts(:

  30. Taylor Camille Says:

    hey, thanks for the great questions, it’ll be fun asking them

  31. Ashley Says:

    Hey Dionis(:
    umm quick question. How do you know if your bf doesnt mind being asked more personal questions??! I dont wanna ask him like wicked personal Q’s and have him be uncomfortable <=] Thanks

  32. Dionis Says:

    Hi Ashley,

    In a way, relationships are like a profound river. The more pure and clear it is, the better and deeper you can see through it.

    We see clearly the other person only when we know them well and this knowledge can come from personal conversations (or in our case, asking questions).

    I understand that your boyfriend might feel uncomfortable, but remember that trust should replace that feeling. Also remember that the answers to these questions are only going to benefit both of you even if they are not what you expected. That is what relationships are about.

    But in your case, I recommend that if you know he will not like these personal questions, its better not to ask then to force him to respond.

    If things change, keep in mind what I have told you because you might never know.

    Thank you so much for your comment. I really appreciate it.

    – Dionis

  33. Letysha Says:

    Wen i askd my boyfriend ol these qtns igot 2 kno the kinda person i reali am n wat exactly i expect in a partner n we’re GETN MARRIED in August next year……bse i fell mo in luv than i alreadi was…..crazy,ryt?

  34. samie Says:

    I love these question’s.!
    My boyfriend thought it was funny when i started asking him these.
    Thanks for writting these[:

  35. oliviaa. Says:

    this helpedd. me and my boyy always text questions and he makes me ask them so i ran out and looked them up. thanks!

  36. Tonya Says:

    This post reallly helped…..When i asked my boyfriend questions about past relationships he got mad at me for “bringing up the past”. He said that I am to much of a jealous person and he thinks we need a break for a little bit so he can get his head clear. I asked him why he thought that we shouldnt talk about the past since he wants to be my future and i want to be his and he stormed out of my apartment. I did a little “research” and i found out the past isnt really the past. He was cheating on me with his ex girlfriend. Aparently, they met up again at the local coffee shop and they’ve been meeting ever since then. I checked his past phone calls and i checked his text messages. She called him baby, honey, sweetheart, love ect… it made me sick. I didnt say anything about it until we got back together. i wanted to catch them in action, so i told him i was leaving for a business trip for the weekend and he was in my apartment. I asked him to watch my cat while i left. I really just went a couple minutes away to a hotel. I asked a good friend to drive by my house every so often to see if anyone else was there. He didnt waste anytime because that night i get a call from my good friend saying she saw someone else there. I grabbed my spare keys and busted in the door. I caught him and his so called “ex” together in my bed. His car got a new bodykit that night…. lets just say, we’re over and im currently dating the love of my life. We are happy and i feel completley connected with him. life is sweet :)

  37. Dionis Says:

    Wow. Tonya I really have to say that I feel sorry for what you have been through. This is something that goes on everyday.

    But what seems incredible to me is that if it were not because of these questions that I wrote, you probably will still be with him and he will still be cheating on you.

    All I can say to you is try to bring peace into your situation with him. Not by revenge, but with understanding. It could be the possibility that if it was you who had an ex boyfriend before him, you could have had the temptation of seeing that ex again.

    I wrote a good post in the past that can help you out:

    Thank you so much for your comment and good luck with your new relationship.

  38. Crysla Says:

    Hey dionis, you shoukd make pick up lines for girls. I currently like this guy in the same class as me and don’t know what to say to him LOL LOL LOL XD
    I am shy and I think he is too. So it’s kinda tough for me to say anything.

  39. Danielle Says:

    this helped alot… i just hope he doent get anoyed :) i will try it lik 10 min…

  40. Aemi Says:

    Thanks! this post really helped me get to know my boyfriend and we enjoyed them really!

  41. momo Says:

    Jesus Loves you!!!

  42. kristin Says:

    do you have anything to tell me about your past i should know

  43. Victoria Says:

    I don’t have a boyfriend, or freinds, or a life, I live with my parents and im 27, my income is 0$, and I was born without legs.
    But hey, If I had a boyfriend, I’d defenetely ask him these questions =)

  44. andrea parker Says:

    Wow….. Nice Information.
    My boyfriend looks pretty good & using this questions
    Now I can learn more things from my boyfriend. LOL…

  45. aveline Says:

    unluckly i dnt believe in boyfriends coz most of them r emptyheaded.
    likewise ths questions aren’t helpful to me

  46. Rainey Says:

    Thank you for these questions! They helped a lot and were very useful! Well done!

  47. catlin Says:

    Me & my bf ask random questions to eachother all the time.
    This helped out, thanks :)

  48. Jasmine Says:

    I don’t understand why if you don’t have a boyfriend, you commented. Anyway, I have a boyfriend that I just started daating and we ask eachother random questions all of the time, but we ran out of questions! So I had the brilliant idea to google questions to ask your boyfriend, but this is the only sight that had questions that weren’t incredibly gross. Thank you so much for giving us great questions that weren’t gross! It was fun to hera what my boyfriend had to say. Thank you!

  49. Dionis Says:

    Hi Jasmine,

    Yeah I know that there are a lot of other sites out there with gross things. But I like to keep the content here good for everybody. From kids, to Grandma; from teenagers to adults.

  50. Briezie Says:

    ^ Yea I’m 14!! So THANK YOU!! Anyway, I like this questions a lot. But I’m kinda nervous to ask my guy.. How would i start a conversation with him if i wanted to ask him one of the kinda personal questions about past relationships and stuff.?

  51. melissa Says:

    omq lik i jus asked muii bf sume of des qustions, he waz straiqht up tweakinq!! lol

  52. melissa Says:


  53. Kenzie Says:

    Thanks Dionis…This was pretty cool.It helped with me and my boyfriend to get closer:).Im 14 and we have already discussed are future….its crazy but i think we will make it:)

  54. YAATRIKA Says:


  55. YAATRIKA Says:


  56. Angie Says:

    ok so, me and my bf have awkward silences, how do I get that to stop?

  57. Krystal Says:

    I love this! great site! you really know what you’re talking bout keep up the good work

  58. Slier ravasua Says:

    thnx 4 d ??? dude….!!!I love this…i ask him and he answered them back….I’m really happy…thnak yu

  59. Krysten Says:

    OMG! Thank you so much for these questions!! My bf and I always play the questions game and I ran out of questions till I saw this site! Its great! Thanks again!!(:

  60. Cheyenne Says:

    Umm thannks for writting these questions down they gave me and my boyfriend things to talk about thannks!!

  61. Dionis Says:

    No problem Cheyenne.

  62. Beverly,my sisters' name too Says:

    Thanks for the questions..i found them useful and handy too..)

  63. Dionis Says:

    Another Beverly.

  64. Dana Says:

    Thanks Dionis! This is really what I needed to help with the question game with me and my fiance…Thanks a million!!

  65. Not a beverly, but a Nikki Says:

    I read these questions and as I have asked some of these already, there are some I have not. So thank you, these are very helpful to ask my potential boyfriend to get to know better. So far so good.

  66. Roderius Says:

    Great question

  67. Michele Says:

    These r very good questions for me to ask my bf. It also gave us more to tlk about.

  68. Sydney Says:

    I have a question: Do you think its wierd for an 11 year old to have a boy friend?

  69. cheli Says:

    thank u so much diz helpd alot 2 know my boo much better thxs :) <3

  70. cheli Says:

    thank you diz helps alot i got 2 noe my boo much better :) <3

  71. Beverly Says:

    Hubby enjoyed it<3

  72. keishaa Says:

    WOW ! Thanks so much this really helped me. My boyfriend and I just started dating a week ago and he decided to play the question game. I couldnt think of anything so i resorted to google and found your post. Uhhmazing really helped (:

  73. Michael Wallace Says:

    Hey there , I am making a site and your articles would really fit in well. Would you care if I copy and paste your article?

  74. Lila Says:


  75. Kayleigh S. Says:

    Hey, dude! Thanks for posting these. I totally just googled “Sweet Things To Say To Your Boyfriend.” We’ve been together for two years now, and we are moving in together. I really cannot wait. <3 So those awkward moments together, now I know what to talk about.

  76. Dionis Says:


  77. Dionis Says:

    Sure feel free to copy all you want. Just make sure to always place a link back to the original post at the bottom.

  78. Dionis Says:

    I am glad he did :-)

  79. emily Says:

    lol thx these made me and my bfs convos much less awkwerd

  80. Asia Says:

    These are some really good questions.. Great way to get to know your boyfriend, I may just try asking my boyfriend these questions.

  81. Mikaela L= Says:

    i started to ask my bf these questions and it can get pretty awkward if your really young like we are or if you cant answer that question because you haven’t had that experience. i know that my bf loves for me to ask questions, but it can get boring after a while. =P good questions though really helps to find out who some one really is.

  82. Alaya Says:

    I don’t have a boyfriend, but I enjoyed asking my best friend (who is a guy) these questions. He enjoyed the experience also. :)

  83. Manderine Says:

    Hey man thanks bunches for this site. It really helped me get to know my boyfriend more.

  84. Shay Ann Says:

    These are great my boyfriend was a little annoyed by some but he’s okay because he love me to much tobe angry!
    But great questions and site

  85. Ann Ominous Says:

    I don’t even know her, but I’m pretty sure her name is Daisy, not Dasiy. Getting her name right, might be a good place to start. LOL Seriously though, she’s just not into you. Accept it and move on.

  86. Omkar Says:

    I have a friend, when i go to my office, she looks at me as she is waiting for me for asking about relatioships. but i afraid because if she is bigger than me. but now i did not see her from the last 1 week but i know the related area of job of her. so i am going at the same area about her information. so what kind of questions should be asked at office related area.

  87. Elizabeth Says:

    last person on this earth? what about the other Earths?

  88. Darien Alexis Says:

    I asked my bf some of these questions but it started to get awkward and we both got really shy about it. Any suggestions of how we can have a good convo but not with all the awkwardness?

  89. priya Says:

    they were wonderful my boyfren was a bit off guard but he got over it

  90. kay Says:

    these questions gave me and my boyfriend something to think about and talk about

  91. Wittlee Says:

    This is awesome so going to use this for the rest of my life. The single one that is*.

  92. jasmine Says:

    These are great questions for humorous growing relationships. Thanks :)

  93. jasmine Says:

    Me and my boyfriend are going through them now :)

  94. InkD3ath Says:

    You should avoid any questions you wouldn’t be comfortable answering yourself. You should also avoid questions that might make him sad or start crying. Also be careful asking intimate questions.

Leave a Reply

WP Login