50 Random Questions to Ask your Boyfriend


There are so many things you’d like to ask your boyfriend. Some of them are serious questions about your future together or his belief system and some of them aren’t that serious. Irrespective of its nature, here is a list of 50 random questions to ask your boyfriend:

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1. What would you do if I run away with someone else right after you tell me that you love me (if he ever does say that)?

2. Have you made a will, just in case you end up dying before you anticipated? Am I in it?

3. If you win $1,000,000 and you have to spend it all in a day, what will you buy? Will you consider donating the money?

4. Do you think adopting kids is a good idea? Would you want to adopt one later on, just so that you can save a life?


5. How much do you love me and what are you willing to do in order to prove your love?

6. Have you ever been in a serious relationship before? How long do you think our relationship is going to last?

7. I hope you don’t get angry but this guy who has been hitting on me wants my number. Can I give it to him?

8. If I ever jump off a boat, would you come after me to try and save me to show how much you love me?

9. If there is one thing you would like to change about me or our relationship, what would it be?

10. What according to you is worse: physical or emotional intimacy with a guy?

11. Is there any incident in your past that you wish had never happened?

12. When you kissed a girl for the first time, did you know how to kiss by then or were you just pretending to know?

13. If you ever got the chance to look like someone else, who would you choose to look like and why?

14. If there is anything you would like to apologize to me for, what would it be?

15. Do you think it’s wrong to lie to people or is lying to save someone accounted as a good deed in your books?

16. Are you a horror movie buff? If yes, then what is the scariest horror movie you’ve seen in your entire life?

17. If you could raise someone from the dead, who would you prefer to raise and what would you ask them?

18. If you ever come across a magic lamp (like in Aladdin) and you get three wishes, what would they be?

19. Have you ever come in close contact with any extra terrestrial beings or felt like you might be abducted?

20. If you became a hamster one day, would you like living in a cage or would you still want to live in your room and sleep in your bed?

21. When you saw me for the first time, what did you say to yourself? Did you feel that we would end up dating each other?

22. If not me, is there any other friend of mine that you would have dated?

23. If you became the richest person on this planet, would you consider buying a country for me?

24. When you were little and you would go to the beach, would you check out other women even though they were much older than you?

25. How old were you when you shagged for the first time? Did it help you to feel relaxed?

26. Have you ever had a scary dream? Do you dream the same thing frequently?

27. Ever since you were a kid, have you considered being a bully? Do you think it’s something that helps people in any way?

28. Is there any other name you would like to be known by other than the one your parents have given you?

29. Is there anything you have done that you are very proud of and if given a chance, would love to show off?

30. Have you ever wanted to live a life identical to your favorite band/singer?

31. Do you like your younger sibling? Have you felt over-shadowed by him in any way?

32. Have you done anything crazy in your childhood just to get some extra attention from your parents?

33. Have you ever taken drugs in your life? Was it easy for you to let go of it?

34. Is there anything about you that you hate and would like to change at any given point of time in the future?

35. What will you do if you find out that your parents are actually your foster parents and your real parents have finally come to get you?

36. Do you think that girls are different from or superior to boys? Would you treat them differently based on their gender?

37. Being a man, do you believe in women’s emancipation? If required, would you support this cause?

38. Do you like your present job or would you prefer to change it if you ever get the option?

39. Have you come up with a savings plan for your future already or are you planning to go with the flow?

40. Do you think both spouses should work in order to make ends meet or would you prefer your wife to stay at home while you go off to work?

41. Do you consider gambling to be a good thing?

42. Have you ever had sex? Which part of it do you enjoy the most and which would you love to avoid for the rest of your life?

43. Do you believe in the concept of ‘saving ourselves’ till marriage?

44. Why is it so difficult for you to show how you feel about me? Is it because one of your ex-girlfriends never valued your emotions?

45. Have you ever slept with someone and sneaked out of her apartment without waking her up and hoping she’d never call?

46. Since we are in a relationship, would you be expecting fidelity from me or is your understanding of our relationship more open?

47. Are you addicted to having sex? What do you do when you don’t find anyone to satisfy your needs?

48. Would you be comfortable to go for a checkup for STD’s with me? Is there any reason for you to be scared?

49. Are you scared of having fertility issues in the future? Did you engage in any activity that might have created this fear?

50. Do you think sexual molestation is prevalent in the man’s world as much as it is in a woman’s world?

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  • Fiona

    These questions sure are random and not to mention fun! Great work!!

  • Shayne

    Question 44, Never ask this question. It is really easy to hurt your partners feelings, Especially how its worded. Awful. Just a mean and terrible question,

  • Fiona

    These were funny to ask my boyfriend

  • Hannah

    funny didn’t ask them all most could have been hurtful

  • C

    These are terrible questions to ask. Way to put some distance in your relationship or break it up.

  • Mali

    Oh my Goodness. These are horrible questions only like 5 of them are usable together. The questions range with things someone would ask in the beginning of a relationship, to questions one should ask towards marriage. If you’re asking about his finances you probably already know about his sex life and morals when it comes to a relationship. Most of these would result in an argument especially 44. Also if you could help it please don’t ask 22, it’ll just result in insecurity.

  • booboo

    my boyfriend and i have been dating for a year now and i heard he was skateing but he dont know how to but his cousin was their but they said he was skateing with another girl but i think it was his cousin and they went to sit down and i dont know what to do bc he is a softy sertin things will affect him a 5 year old girl pushed him down a hurt his ribs and made him cry and i dont want it to come out wrong and i can tell him any thing but he so nice to me but i dont want to hurt him and i really got mad when he was talking to a girl and i dont like her and she dont like me so what can i do about that too and i just dont know what to do tho. but what can i say to him?