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129 Questions To Ask Your Boyfriend - Get To Know Your Partner Better


Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on, iHeart Media, Elite Dai ...
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by | April 11th, 2021

If you’re out on a date and wishing you had some fun questions to ask your boyfriend, you’re in luck! This fun list is packed full of interesting, and creative questions to ask a guy you like, along with some deeper questions to ask a guy you have been seeing for a while!

You probably know how to start a conversation with a guy, but sometimes it can feel like the dialogue kind of stalls out.

These questions will help things going again, and are sure to lead to some fun discussions!


17 Best Questions To Ask Your Boyfriend

These are the best of the best questions, great for starting a conversation any time. You don’t have to do them in order, just find a few that sound fun!

Don’t forget to take notes (maybe, later, so it doesn’t feel like a test!) - some of these have great info in them!

Here are the 17 best questions to ask your boyfriend:

1. Do you consider yourself a happy person?

What is his definition of happy?

2. What would you do if a guy was interested in you and asked for your number?

Or, what about another girl?

3. What is your favorite thing to wear to bed?

And if it's socks, it may be time to end things… kidding!

4. Is there anyone you are afraid of?

What's the back story?

5. What would you say to your President if you ran into him randomly?

Would he be starstruck, or would he start hitting on some issues?

6. What are the three things that you wouldn’t change about your life, no matter what?

In no particular order, of course.

7. If you won a trip to go anywhere on earth, where would you take me?

Where will he take you?

8. What do you feel is the world’s biggest problem right now?

And how would he fix it?

9. If money was not a factor, would you leave your job and travel the world?

If so, would he travel randomly, or make a detailed plan?

10. What is the most expensive thing you have bought for yourself?

Besides a car...

11. What are you truly obsessed about? Are you ashamed of it?

Those guilty pleasures plague us all.

12. Do you like my friends?

Does he think his friends like you?

13. What country would you never want to visit?

What does he know about it that keeps him away?

14. How do you waste your time?

Maybe it’s video games on his phone, scrolling Insta, or reading a good book.

15. You're in prison with a life sentence, what was your crime?

Get creative - there are lots of weird crime laws on the books!

16. What’s your stance on PDA?

Is he comfortable with it, or prefer not to be affection in public?

17. What is your spirit animal?

A feisty tiger? A content koala?

19 Questions To Ask Your Boyfriend To Get To Know Him

If you want some questions to ask a guy to get to know him, this is the list for you! Find out what he likes, dislikes, what makes him tick!

Here are 19 questions to ask your boyfriend to get to know him:

18. Do you think money can buy happiness?

What can he buy that makes him happy?

19. What motivates you?

Fear or reward?

20. How long was your longest relationship? Why did it end?

What would you do if you randomly ran into them?

21. What has been the best year of your life so far?

Was it recently? If not, why is that?

22. What one thing do you want to accomplish in your life?

What does he want his legacy to be?

23. What fictional character do you have a crush on?

It can be from a book, movie, comic, tv show - player's choice!

24. Have you ever lived with a partner?

What were the pros and cons of that?

25. If you could wake up tomorrow and be fluent in any language, what language would you choose?

Why would it be useful?

26. Where is your ideal place to live?

Is he a city mouse or a country mouse?

27. If you could bring one person back from the dead for a day, who would it be and what would you do?

Who is the GOAT?

28. Have you ever been given a fake number?

Why do you think that happened?

29. Would you ever go on a silent retreat?

When thinking of things to ask your boyfriend, it's a great idea to ask how he feels about taking contemplative time.

30. How important is religion or spirituality to you?

Is it an annoyance or a north star?

31. What is the hardest decision you've ever made?

Does he think he made the right choice?

32. Who was your first crush?

What does he remember most about them?

33. Who would you want to trade lives with for a day?

Someone famous? Someone smart?

34. If you named a drink after yourself, what would it be?

What flavors would be in?

35. What is your deepest darkest secret that nobody else knows?

Remember to cross your heart, promise not to tell!

36. What is something you’re secretly insecure about?

Reassure him that you’ll never tease him about this.

16 Fun Questions To Ask Your Boyfriend

So, you’re on a date and trying to get to know each other better, but the conversation gets a bit stuck. No fear, help is here!

These are some amazing, fun questions to ask a guy that will get you guys connecting in a whole new way!

Here are 16 fun questions to ask your boyfriend:

37. Out of your friends and family, whose relationship do you admire the most?

What about it makes it so attractive?

38. What was your very first impression of me when you first saw me?

Tell him to be honest!

39. How would you describe our first kiss?

Was it as good as he hoped, or more awkward than he expected?

40. Do you like when I touch your face?

Are there parts of it he doesn’t like touched? This might just be one of the best things to ask your boyfriend.

41. What's something I do, that I don't realize I do, that you love?

Maybe something silly, like twisting your hair.

42. Would you ever write a song for me?

What instrument would he play it on?

43. Am I the kind of girl you’d take home to your parents?

Ask how his parents reacted to other girlfriends.

44. Has a sad movie ever made you cry?

Does he like to watch sad movies or does he feel manipulated?

45. How old were you when you had your first kiss?

Where was it? Did he tell anyone?

46. Who knows you best?

His best friend? His mom? You?

47. What’s your favorite thing about traveling?

Is it before, during, or after?

48. If I was a dessert, what would I be and why?

Something thrilling like ice cream or decadent like lava cake?

49. What actor or actress would play you in a movie about your life?

Someone funny? Serious? Devastatingly handsome?

50. Do you think you’re a good kisser?

Describe what makes a good kiss.

51. Have you ever laughed so hard you peed your pants?

If so, how did he fix the situation?

52. Is there a song that you think of when you think of me?

Have him sing it to you!!

19 Funny Questions To Ask Your Boyfriend

Looking to add a little silliness in your relationship? That’s great! Studies show that couples that have fun together stay together longer!

Try using these funny questions to ask a guy to get some good, wholesome wit going on!

Here are 19 funny questions to ask your boyfriend:

53. How often do you pee in the shower?

For real, let’s hear it.

54. Have you ever put on makeup?

Does he feel that it is taboo?

55. What is the most embarrassing thing someone has caught you doing?

And how did he recover??

56. What’s the food you like to have the most on your birthday?

Besides the birthday cake, of course!

57. Can you remember the funniest thing you ever did or said?

Have him describe why it was so hysterical.

58. What was your favorite thing to wear as a child?

Would he wear it now as an adult?

59. What is your grossest habit?

And is he opposed to… stopping that?

60. Are you a fan of selfies?

Why or why not?

61. Have you ever kissed another guy?

Would he?

62. Would you rather be a vampire or a zombie?

Let’s debate strengths and weaknesses.

63. Did you have a funny ambition when you were a kid?

Did it come true?

64. Did you have a nickname that you hated when you were a child?

Was it from a loving friend or a bully?

65. What is the dumbest movie?

Does he watch it anyway?

66. Out of all the world's languages, which one sounds funniest to you?

Which language does he think is the hardest to learn?

67. Are you of the naughty or nice variety?

How often does he play pranks? What if other people don’t like them?

68. What would be the one meal you could eat every single day and never get bored?

For me, it’s sushi, hands down.

69. What was your favorite childhood toy?

Do his parents still have it?

70. What is the first thing you'd do if you heard about the outbreak of zombie apocalypse?

Find locked shelter? Secure a vehicle?

71. Which weapon would you pick for your zombie apocalypse survival?

Are we talking grenades or axes?

20 Interesting Questions To Ask Your Boyfriend

Asking people questions about themselves helps them feel like you are truly interested in them. These interesting questions to ask a guy will send him the message that you want to know all there is to know!

So pick a few and become an expert on your new favorite subject- your guy!

Here are 20 interesting questions to ask your boyfriend:

72. Do you like kissing in the dark or kissing in the rain more?

As long as there is kissing, it all sounds good.

73. If I was scared, would you hold me?

What does he do when he is scared?

74. What was the best thing about how your parents raised you?

What was the worst?

75. What’s something you tried really hard to like but just couldn’t?

Maybe its a food, a sport or a TV show everyone else loved.

76. What are the manliest and least manly things you have ever done?

On a scale of zero to manly, let’s rate things.

77. What are your biggest fears about relationships?

How can you make him more comfortable with those?

78. What is your definition of intimacy?

How is it built?

79. What do you like to spend money on?

What does he NOT like to spend it on?

80. How many times have you been in love?

Does he feel like that’s not enough? Or too many?

81. What is a relationship deal-breaker for you?

Has it broken up a relationship for him before?

82. Can you overlook anything from your partner’s past?

Can people really change that much?

83. Do you believe in monogamy?

If not, what does he think healthy relationships look like?

84. What would you do if your partner became physically disabled?

Would that be too hard to handle? How would he measure?

85. What is your relationship with your father like?

How could it be better?

86. What keeps you up at night?

Does he stress dream or stress lay awake?

87. Cuddling or kissing, which is your favorite?

They both have their benefits.

88. What is your slogan?

If he had to get a tattoo of it, where would he put it?

89. Do you believe in fate?

How much control do we have over our lives?

90. What do you see as ‘couple’s goals’?

Running 5k’s Thanksgiving morning? Coordinating tattoos?

91. What is your most humbling experience?

What did it change for him?

18 Random Questions To Ask Your Boyfriend

Looking to kill some time? Don’t scroll Instagram - use this list of random questions to ask a guy to put that time to good use!

Here are 18 random questions to ask your boyfriend:

92. Are you afraid of getting old?

What are you most looking forward to about it?

93. Do you think about your past often?

With warm memories, or regret?

94. Do you feel like your life is meaningful?

Describe what a meaningful life looks like.

95. Have you ever felt truly understood?

Who was that with?

96. Do you think astrology is crazy or real?

What about other things like that?

97. What do you think is overrated?

Avocado toast, the NFL, or something else?

98. What lifts your spirit when you are down?

Maybe there is a person or a certain type of music that he likes.

99. If you could win A ‘Lifetime Supply’ Of Anything, what would you want it To Be?

Besides money, of course.

100. What do you do when you’re exhausted?

What does recharging look like for him?

101. On the off chance that you find $100 on the floor at this moment, what might you do with it?

Is he a saver or a spender?

102. How did you spend your time off school as a kid?

Did he have neighborhood friends?

103. Do you believe in happily ever after?

What does that mean for him?

104. What are your thoughts on marriage?

How will he know when he’s ready?

105. What do you consider a wasted life?

Who gets to decide?

106. Do you want kids?

If so, how many? Boys or girls?

107. Have you ever thought of being a woman?

What does he think would be some of the biggest differences in being a man?

108. What kicks your adrenaline?

People getting aggressive? Roller coasters? Thrill of the deal?

109. What is your favorite romantic place ever?

He doesn’t have to have been there before.

11 Deep Questions To Ask Your Boyfriend

These deep questions to ask your boyfriend will get everyone moving in a more serious direction, stat! Make sure you handle these questions with care - there is a lot of vulnerability being spoken here.

And on that note, don’t be afraid to respond with your own answer. You being open helps create a culture of trust.

Here are 11 deep questions to ask your boyfriend:

110. What is your happiest memory from our relationship?

This would be a good answer to write down and remember.

111. What is your favorite thing about our relationship?

Is it something that comes naturally or something you guys have to work at?

112. If we could recreate one day from our relationship, what day would you choose?

Would he do anything differently?

113. What should I do more of? What should I do less of?

Again, take notes!!

114. What is something you are guilty of taking for granted?

What are some ways to cherish that more?

115. Do you think we need to spend more time apart or more time together?

What is the ideal alone/together ratio?

116. If I had to move away really far, would you come with me?

Would it matter where it was?

117. Would you sacrifice for a stranger?

How much? $10? $100? A kidney??

118. Would you risk your life to save mine?

What about someone else? How would he feel about someone sacrificing for him?

119. Do you think relationships are intended to last eternally?

What will they look like after this life?

120. Do you ever feel the need for immense love?

What makes him feel loved, safe, and seen in those moments?

121. What habits do you have that annoy other people?

Is it his responsibility to change them?

122. What makes you angrier than it should?

Why is that a trigger?

123. Are we significantly less happy in this era of technology?

How can we keep a balance with all of its benefits?

124. What movie was so sad that you will never watch it again?

Was it his idea to watch it in the first place?

125. What are the two biggest lessons you’ve learned from previous relationships?

Did he learn them the easy way or the hard way?

9 sexy questions to ask your boyfriend

How about some sexy questions to ask your boyfriend that will drive him crazy and possibly get him in the mood to do whatever you want. With these questions, you'll definitely be in control of the situation.

Here are 9 sexy questions to ask your boyfriend:

126. What’s your favorite way to be seduced?

Take notes, and use this on him the next time you're in the mood.

127. What's the most sensitive part of your body?

This is definitely a question you already know the answer to.

128. I come home from work stressed, how do you relax me?

Let him show you, rather than tell you.

129. Do you like wearing boxers or briefs?

And tell him which you prefer him to wear, also.

How To Pick The Best Questions To Ask Your Boyfriend

So, there are almost a million questions here, how do you even start? I’ve made a quick little guide to help you make the most of this extensive list of queries.

Here is how to pick the best questions to ask your boyfriend:

1. Check your bandwidth

There are times for having deep and probing conversations, and there are definitely NOT times. Make sure you and your guy are in a good space, aren’t having a little spat, not struggling with a big decision, and aren’t tired, hungry, or lonely.

You’ll have the most fun and have better conversations when you’re hearts and minds are open to connecting. Trust me, it’s worth the wait.

2. Pick questions that apply

Don’t just start at the top and start blasting away - some of these questions are more suited to a serious relationship. Don’t scare away a potential partner by asking him to tell you his darkest secret on your first date.

Start slow and easy, and as intimacy builds, feel free to start moving into deeper waters.

3. Be vulnerable and trustworthy

I mentioned it earlier - be open yourself with answering these questions. This shows your guy that you are willing to create a space that is safe for these deep questions!

And be careful with his answers - when he tells you his insecurities or about a happy memory, make sure to thank him for sharing his thoughts, and NEVER use it against him in a fight.

Downloadable and Printable List of Questions to Ask Your Boyfriend

Here is a downloadable and printable List of Questions To Ask Your Boyfriend (right click the image and select Save Image As...):

More Great Ways To Talk to Guys

  1. Maybe you want to use these questions with your boyfriend, but you need a boyfriend first! Start at the beginning and use this helpful list on how to ask a guy out!
  2. Check out our go-to guide on how to flirt with a guy, if you’re looking to add a little playfulness to your dating life.
  3. When you’re wondering, should I text him?, follow this step by step guide to know for sure!

In Conclusion

Now, you have more questions to ask your boyfriend than you know what to do with! Next time you’re trying to remember how to start a conversation with a guy, just break out this handy list and find some great conversation kindling!

Search through the list whenever you think "I wish I had questions to ask my boyfriend". Great conversations are just ahead - have fun!

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