Fun Questions to Ask Your Boyfriend (2022)

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fun questions to ask your boyfriend

You’ve been dating your boyfriend for a while now, and you’re pretty sure you know everything about him—or do you? You might be surprised to find out there are tons of fun questions to ask your boyfriend that will surprise him, make him laugh, and maybe even help you two grow closer together!

Fun questions to ask your boyfriend

Here are 100 fun questions to ask your boyfriend that will make you both have fun together!

You probably already know that it’s important to ask questions in order for your relationship with your boyfriend to last. These fun questions to ask your boyfriend will help you break free from routine and bring some spice into your life and your relationship!

1) What kind of underwear are you wearing right now?

2) When did you have your first kiss?

3) How did the first kiss make you feel?

4) What was one of your favorite things about our first date?

5) What is something that makes you laugh that I don’t think is funny at all?

6) What’s your favorite thing about me?

7) If you had to pick one superpower, what would it be and why?

8) Is there anything you want from me but haven’t told me?

9) What is your dream vacation?

10) 5) If you could have dinner with any 3 people, who would they be?

11) How many kids do you want (in total)?

12) Do you like sunsets more than sunrises? Why or why not?

13) Have you ever been in love with someone who didn’t love you back?

Questions That Can Strengthen Your Relationship

Related: Amazing Deep Questions To Ask Your Boyfriend

fun questions to ask your boyfriend

14) Who are your current closest friends?

15) As a child, what did you want to be when you grew up?

16) Have you ever been arrested or in trouble at school or work?

17) Do you enjoy watching movies on the couch or simply relaxing in general?

18) Are you more of an introvert or extrovert?

19) What makes you feel sexy?

20) Who was your first love interest?

21) When was the last time we had sex, and how long did it last?

22) Are you more likely to text me during work hours or late at night after I go to bed?

23)What’s your biggest pet peeve?

25) Would you rather stay in all weekend or go out every night with your friends?

26)What three things can’t you live without?

27) If I asked your family members to describe you, what would they say?

28) How old were you when you lost your virginity?

29) Did you grow up in a house with both parents?

What questions do guys like to be asked?

30) Did you graduate high school?

31) Did you graduate college?

32) Did you go to college far away from home or close by?

30. How many siblings do you have and how old are they?

31. Do you think our relationship will lead to marriage someday, or am I just someone fun to date right now?

32. Are there any tattoos that I don’t know about yet that might surprise me if I saw them tomorrow morning while getting ready for work?

33. What does your ideal house look like?

34. How often do you masturbate?

35. Have you ever cheated on anyone before?

36. Would you cheat on me if given a chance?

37. Do you think I’m attractive enough?

Questions to ask your boyfriend for fun

Related: Questions to ask your girlfriend


Relationships are hard work. Anyone who tells you differently is lying. But that doesn’t mean your relationship has to be boring! In fact, adding some fun activities and questions can make your relationship stronger and more passionate. You know what they say, right? Variety is the spice of life! So, mix things up with these fun questions! Here are other questions to ask your boyfriend for a fun time together:

38) What is one thing I always do that annoys you?

39) How many times have I hurt your feelings by accident in my day-to-day life?

41) Which superpower would we have if we were superheroes?

42) What’s one thing I do that makes you feel like I love you most?

43) What’s something I could do that would make you fall even deeper in love with me?

44) What was your first impression of me when we first met?

45) When did you realize you loved me?

46) When was our best date ever?

47) When was our worst date ever?

48) Where is one place we should go on vacation but haven’t yet gone to together?

49) What is one thing I don’t know about you that you wish I knew? 1

50) What is your dream job?

51) If we had children, what names would we give them?

52) What will be our next big adventure as a couple?

53)Have you ever been in love before me

54) Who was your childhood hero/role model/idol growing up (and why)?

How do I get him to open up? (Ask Him This Questions) :

55) Is there anything that I can do better right now to improve our relationship?

56) If you had one wish, what would it be and why

57) If you had three wishes, what would they be and why

58) Tell me something that was hard for you when you were younger

59) Have you ever had an out-of-body experience

60) What was your favorite book as a child

61) What is one talent or skill I don’t know about you? (Answer with an awesome story)

62) If I wasn’t in your life, how would that affect you?

More questions to ask your boyfriend for fun :

63) What was your favorite toy as a child?

64) What’s your favorite time of day?

65) What would you do if you won $1 million dollars in a lottery?

66) If you could have any superpower, what would it be and why?

67) Where is your favorite place to eat?

68) Where is your dream vacation spot?

69) Who are the five people that you admire most and why?

70) What’s one thing that makes you unique compared to other people?

71) What is something that annoys you about me, but I don’t know about it yet ?

72) If we had children, what names would we give them and why?

73) If you could live anywhere in the world, where would it be and why?

74) When did you feel happiest recently?

75) When did you feel worst recently?

76) When was your last panic attack?

77) Have you ever been to therapy before and if so, how did it help you?

78) Are there any causes that you’re passionate about?

79) Are there any books that have changed your life?

80) What do you think our children will look like?

Ask him this also :

81) If you could choose anyone in history to dine with, who would it be and why?

82) What has been your biggest failure up until now, and what did you learn from it?

83) What has been your biggest success up until now and what did you learn from it?

84) What’s your greatest fear?

85) What’s your wildest fantasy?

86) If you could change anything about yourself, what would it be and why?

87) Would you rather win an Olympic gold medal or Grammy Award, and why?

88) Would you rather have superpowers or money, and why?

89) Would you rather be famous for doing something good or infamous for doing something bad and why?

90) What does true love mean to you?

What questions would you ask to build the relationship?

91) If you could only listen to one song for the rest of your life, what would it be and why?

92) Which historical figure do you most identify with, and why?

93) Which fictional character do you most identify with and why?

94) Which current athlete do you most identify with and why?

95) If you could ask God one question, what would it be and why?

96) Is there anything that you believe in that most people don’t agree with?

97) Is there anything that you disagree with strongly enough to argue about?

98) What was your first car/motorcycle?

99) When was your first kiss, and how did it make you feel?

100) Describe your best date ever.

More questions to ask him when bored :

101) Describe your worst date ever.

102) What do you consider to be your best physical feature?

103) What do you consider to be your best personality trait?

104) If you had a theme song, what would it be?

105) Who is someone that you miss dearly and wish they were still alive today?

106) Who are some of your heroes in real life and why?

107) What is your best and most important achievement in life?

108) If you could relive one moment in your life, which would it be and why?

109) What’s something that you’ve always wanted to try but haven’t done yet?

110) What’s something that you’ve always wanted to buy but haven’t bought yet?

111) What are some of your favorite hobbies or activities outside of work and family time?

112) What do you want to be remembered for after you die?

113) What is your idea of perfect happiness?

114) What would you tell your younger self if you could go back in time?

115) If you could be born again, what age would you come back as and why? 5

116) If you could invite anyone to dinner, living or dead, who would it be and why?

117) If you could have lunch with any person in history, who would it be and why?