TheCoolist is a mood board for your headspace.

    Questions to Ask Your Boyfriend: 157 Intimacy Building Questions
  1. TheCoolist
  2. Life

Questions to Ask Your Boyfriend: 157 Intimacy Building Questions

How well do you actually know your boyfriend? This list of questions to ask your boyfriend will see to it that you learn everything there is to know about the love of your life.

Questions to Ask Your Boyfriend

Having a boyfriend is, hands down, one of the best feelings in the world. But how well do you actually know him? And we don’t simply mean knowing his favorite sport or his dream car, but also knowing him as a person: your partner’s values, favorite memory, biggest regret, and greatest dream. 

Sometimes, having an enjoyable Q&A session with your partner is what it takes. And here are a bunch of questions to ask your boyfriend!

What Are Good Questions to Ask Your Boyfriend When Bored?

Connecting with your boyfriend on a deeper level will build mutual understanding and bring your relationship to a new level of intimacy.

“Communication is the fuel that keeps the fire of your relationship burning. Without it, your relationship goes cold.” -William Paisley.

But where do you start? Ask your boyfriend some questions! 

And here’s a quick tip: swap out the meaningless small talk and the old “how was your day?” line with creative questions that sparks fun and meaningful chats.

10 Good Questions to Ask Your New Boyfriend

At the beginning of every relationship, it’s important to make an effort to get to know your partner. Most of the time, it’s as easy as asking your boyfriend a few specific questions to give you a good idea of who he is and spark even deeper conversations

Fun Questions to Ask Your Boyfriend

Here are a few intimacy-building questions to ask in a new relationship.

1. What makes you feel the most loved?

Gifts? Touch? Quality time?

It’s super important in a relationship, especially one that’s still new, to know each other’s love language. Asking your boyfriend about his preferred way to give and receive love will help your relationship move forward as healthily as possible. 

2. If you could plan a perfect day, what would it look like?

This one is a perfect conversation starter, and you’ll have plenty of ideas about things he likes after your talk. You can also find some exciting stuff to do together if you share a passion for certain activities. 

3. What is your guiltiest pleasure?

Does he have a sweet tooth? Does he sing in the shower? Is he super obsessed with his beard?

Asking him about his guilty pleasure can lead to funny, sometimes embarrassing, conversations.  

4. What is the manliest thing you’ve ever done? The least manly?

What is his concept of manliness? His answer to this question will show you that. And it’s also a fun query that can lead to some interesting answers and stories. 

5. What’s the best mistake you’ve ever made?

His answer won’t probably tell you much, except that you’re most likely going to hear some interesting stories. And good stories are always welcome because who doesn’t love them?

6. What are your expectations for our relationship?

Are you on the same page? Is he comfortable just seeing where things go, or does he hope to be married in the fifth year? Establishing expectations early in the relationship is wise. And since this question doesn’t usually come out of the blue, how about asking this one to your new boyfriend directly instead?

7. What is something that most people underestimate or overestimate about you?

This question will give you an idea of how your boyfriend thinks about how other people view him and how he views himself. If your guy answers humbly, that’s a pretty good sign. But if he sounds delusional, that is usually not a very good sign. 

8. What’s something that you should probably do but will never do?

He probably hasn’t been asked this one. So, let him think a bit about it. But whatever the answer he comes up with, it’s most likely going to be a pretty enlightening and interesting one. 

9. What are the top three lessons you’ve learned from your previous relationships?

Most likely, they have been with others before you. But there’s no need to get jealous of his last relationship. In fact, it’s worth hearing why those relationships are now in the past. Asking your new boyfriend this question will let you know a lot of things, like his deal-breakers or his biggest pet peeve in a relationship.

10. What’s something that makes you angrier than it should be?

Not many would ask this one for their new partner, but it’s an important one. You’ll want to know what stuff makes him angry so you can avoid it. But if there’s no way for you to avoid it, you might want to reconsider the relationship. After all, too much anger will make even the most loving relationship toxic. 

24 Cute Questions to Ask Your Boyfriend

There’s nothing more exciting and fun than getting to know your significant other in a lighthearted way, not too pushy like you’re some kind of FBI agent. And that goes whether you’ve been dating for six weeks or six years. 

Cute Questions to Ask Your Boyfriend

Whether you are trying to grow your intimacy or just trying to be cute with your honey, here’s a list of cute questions you can ask him. 

11. When did you first realize that you like/love me?

12. What comes to your mind whenever we’re not together?

13. If I could, would you like me to read your mind?

14. What was your first impression of me?

15. What’s something quirky about me that you ironically adore?

Aww. Don’t ever feel shy asking your boyfriend this one. It’s one of the best cute questions you can ask him that will give you some blush-worthy answers.

16. Truth or dare?

17. What does it make you feel whenever you hold my hand?

18. What was something about me that attracted you at first sight?

19. If I need to move somewhere really far, would you consider having a long-distance relationship, or would you follow me?

20. Is there any song that instantly makes you think about me whenever you hear it?

21. If you could fight any animal with bare hands and win, what animal would it be?

This one will question how effective those guns are. 

22. If everything happens for a reason, why do you think we met?

23. Would reading a love note that I wrote for you give you butterflies?

24. What would you do if I got distraught to make me smile?

25. Have you ever dreamed about me? What was it about?

26. What made you decide it was time to say I love you?

But before asking this question, make sure he’s said those three words already. Otherwise, awkward. 

27. Is there a movie you want us to watch together?

28. Would you shout my name for the entire world to hear?

29. If you could only describe me in one word, what would it be?

30. Would you still think I’m cute when I look like a mess?

31. If I get scared watching horror movies, would you hold me?

32. Can you tell me something that I texted you that made you smile?

33. If I were a dessert, what do you think I would be and why?

34. If you were Jack and I was Rose in Titanic, would you have tried to fit on the door/raft so our love could survive the icy waters?

20 Fun Questions to Ask Your Boyfriend

Although you might be in a serious relationship, that doesn’t mean everything has to be so serious all the time. It never hurts to keep the mood a little lighter sometimes! A little silliness and a lot of laughter later go a long way in getting your bond stronger. 

Get to Know Your Boyfriend

Asking funny and random questions is the perfect way to catch him off guard. This list is perfect whether you are searching for funny questions to pass the time or simply looking for good questions that will give funny responses. You’ll both be really glad you had these conversations!

35. If you could have a pet, any animal you like, what would you pick and why?

36. What will the job description be like if you can create your ultimate dream job?

37. What’s your most awkward first kiss story?

Come on. Don’t be shy! It’s not a weird question at all. We all have some embarrassing stories to tell. 

38. What’s the weirdest thing a girl has ever done for or told you?

Was it a bad pickup line? Cringe-worthy flirting? This fun question can surely elicit even funnier stories. 

39. What’s the most embarrassing thing you would willingly do for a million dollars? 

40. Can you tell me the biggest lie you’ve ever told a girl to get her to like you?

41. What are some of your favorite memories of going to an amusement park?

If he tells you he can’t remember anything or, worse, he hasn’t gone to an amusement park, add that to your bucket list date ideas, quick!

42. If you could be the first person to achieve something monumental, what would the achievement be?

43. What do you think would be the best Halloween costume for us as a couple?

44. If you could pick a fictional character for a best friend, who would you pick?

45. Who would you pick if you got stuck on a desert island and could only bring three people to help you survive?

46. What’s your favorite TV show or movie that you’re embarrassed to say you’re obsessed with?

47. What’s the lamest thing you did to make your first crush notice you?

Did you pull on her pigtails in the playground? Savage. 

48. If you could get the first kiss with your celebrity crush in a movie, who would you do the kissing scene with?

49. Were you ever guilty of peeing in the swimming pool and acting like you didn’t when someone asked about it?

You have, haven’t you?

50. What was the weirdest thing someone has caught you doing?

51. Could you make your best animal sound for me?

52. Would you tell me your lamest skill?

53. What is grosser than the other: yellow fingernails or yellow teeth?

54. If you could be someone famous for anything, what would that be?

20 Personal Questions to Ask Your Boyfriend

Although some boyfriends are more than happy to talk about themselves or chatter on without prompts, others can be very private about their personal lives. That doesn’t necessarily mean they don’t want to share stuff with you. Just consider them needing a little bit of push before they can spill the tea. 

Intimate Questions for Your Boyfriend

And in this case, you can ask him some personal questions that will help you know and relate better with him.

55. What makes you excited whenever you think of tomorrow? How about the biggest fear about tomorrow?

56. Imagine your personal hell. What does it look like?

57. If your life was a movie or a song, what would it be?

58. If you can be brutally honest, what truth about yourself can you share with me?

59. When do you say was the most defining moment of your life?

60. Can you tell me an instance when you tried hard for something, giving it 100% and more, and your effort still wasn’t enough?

61. How lucky do you think you are?

62. What’s something about other people or what they do that quickly make you uncomfortable?

63. What is the greatest moment that you missed out on?

64. What is your temperament?

It’s a major question you shouldn’t miss out on if you want to know him and his personality on a deeper level. And knowing your man’s temperament perspective will save you a lot of stress later on. 

65. What was the most painful news/words someone has ever told you?

66. Who are the family members, including extended family, who impacted your life most?

67. If you have a videotape of your whole life, but you can only rewatch some of it, what scenes would you like to watch?

68. What’s the most clever thing you’ve ever done?

69. What do you believe makes you unique from other guys?

You’ll have your opinion on this one. But it could be interesting to know your boyfriend’s perspective on this.

70. What’s the worst thing you can do when you get absolutely angry?

71. What makes you feel appreciated or heard the most?

72. Suppose you’re Aladdin for a day, and you get three wishes. What would you wish for?

73. What was the biggest risk you’ve taken, failed, but never regretted one bit?

74. Can you tell me something that you’ve stolen? 

It can be anything, really. Candy in a convenience store when he was five or your heart when he first met you. 

20 Deep Questions to Ask Your Boyfriend About Life and Your Relationship

There’s power in deep conversations in every couple. Asking your boyfriend the right questions at the right time can lead to breakthroughs in the most critical aspects of each of your lives as well as your relationship. 

Great Questions to Ask Your Boyfriend

After all, understanding your partner is the gateway to love and compassion. Instead of just wondering about it, asking these deep questions will help you learn all the why’s about your partner: why he thinks or behaves a certain way. 

75. What’s the best and worst relationship advice you’ve ever gotten from someone? And from whom was it?

76. What’s something you’ve done but will never do again, no matter what?

77. What is the basic recipe for a healthy long-term relationship?

78. If you could give the best advice about life to a teenage you, what would it be?

79. How important would you say having a good conversation with your partner is to make the relationship work?

80. For you, what would a successful life look like?

His answer to this question will allow you to understand your boyfriend’s values, moral codes, and end goals. It could align with yours or not. 

81. What made you cry the last time?

82. What are some telltale signs that you’re very stressed that no one knows?

83. When was the angriest you’ve ever been?

84. Do you think it’s ever okay to have a close female friend or a female best friend? What are the boundaries?

85. Do you think “emotional cheating” is cheating?

86. What’s the most vulnerable you’ve ever been?

87. Have someone broken your trust that it became irreparable?

88. What would be the worst thing I can do to make you want to end the relationship right away.

This is a tricky question and can sometimes be triggering for other people who have had bad experiences in their past relationships. But if he’s open to answering this one, it will give you a clear idea of his relationship deal breakers. 

89. If you could make five rules before going into a serious relationship, what would they be?

90. Are there any conversations you wish we would stop having?

91. What’s something that you are most ashamed to admit?

92. What’s something about you that changed the most in the last ten years?

93. How would you want to spend the next ten years of your life?

94. What is the worst thing that would cause you to escape and go on a road trip alone?

20 Flirty Questions to Ask Your Boyfriend

Before we dive into some good flirty questions to ask your boyfriend, let’s spell out how to ask such questions: be sweet, fun, subtle, or downright flirty, depending on what the mood calls for.

Flirty Q&A

Now, what are some good questions to ask your boyfriend? Here are a few great ones that will keep up the much-needed flirt game in your relationship. And if you are looking for always-hit pillow talk topics, here’s a list for you!

95. Imagine an ideal date. What would we do? Where would we go?

96. What favorite pet names would you like me to call you?

97. What are the most romantic pop culture moments you can think of?

98. Can you tell me three things that never fail to make you smile?

99. What couples activity would you want us to try?

100. If you can only choose one, which one will it be: hugging me for ten minutes or kissing me for five seconds?

What a tough choice!

101. If we were to dance to a song, what song would you play?

102. What’s something you’ve always wished you could do with your significant other but have never done it before?

103. What kind of clothing do you think I look the best in?

104. Would I be shocked if I looked at the search history of your web browser?

105. Would you rather take a bullet or kiss me all day?

That shouldn’t be difficult for your boyfriend to answer. 

106. What’s your favorite photo of me? Of us?

107. Have you ever visited a nude beach? If not, would you ever consider going?

108. Would you love it if I kissed you in public?

Some guys are very low-key, while others love public displays of affection. So, before you steal that kiss, you might as well ask him if he’s okay with it just to be safe and avoid a potentially awkward moment. 

109. What goes in your mind whenever you close your eyes when kissing me?

110. Before we even got together, have you thought about what it will be like to kiss me?

111. If I went inside your bedroom at night, what would I see you wearing?

112. If I look into the photos on your phone right now, what pictures would surprise me the most?

113. Are you certain you’re a good kisser or do you want us to test it out, and I’ll tell you if you are?

114. What would you call it if you could turn our story into a movie scene?

23 Romantic Questions to Ask Your Boyfriend

While good communication is a must-have in every relationship, so is romance. Lack of it can make you and your partner more like friends who’ve known each other for years than lovers. 

Hence, maintaining romance and intimacy is important to keep relationships lively, exciting, affectionate, and meaningful. And as simple as it is, asking these relationship questions to your boyfriend can make them feel desired and loved and add a little of that much-needed giddiness in your belly.

Romance isn't Dead

And even newer relationships can benefit from these romantic questions to ask your boyfriend, as it will reveal a lot about your compatibility. 

115. What’s your favorite thing about our relationship?

116. What would be the craziest thing you can do in the name of love?

117. Where do I fit in in the next five years of your life?

118. How many children do you think we should have whenever we’re ready for kids?

119. What is one difference between us that you think makes our relationship quirky and adorable?

You may like a lot of similar things, but there are surely some differences between the two of you as well. And sometimes, that isn’t such a bad thing. In fact, that palpable difference makes the relationship exciting and can even add a little more intrigue and attraction between the two of you.

120. If you could bring me to a place you absolutely love, where would it be?

121. What do you think you bring to our relationship? What about what I bring in our relationship?

122. What’s something about us, or me, that you miss the most whenever we’re not together?

123. What’s something I can do that will instantly make your mouth drop open and make you speechless?

Knowing your boyfriend’s answer to this question is one tip you can use to help you stay attractive in his eyes. 

124. How do you like to spend time with me? 

125. What do you like the most about spending time with me?

126. What would you want our first kiss to look like if you could rewind your love life?

127. Do you like us holding hands or me holding close to your arm while walking?

128. How often do you think of kissing me whenever we are together?

129. What’s your favorite part of my body that you want to touch the most?

130. What do you think made me fall in love with you?

Don’t be shy to ask your boyfriend this question. It’s time for him to spill the beans on what old tricks he used to get you to fall for him. Was it his undeniable charm or his inherent flirting skills?

131. When you first saw me, did you imagine that we would last thing long?

132. When did you first realize that you wanted to pursue me?

133. Do you think we could improve our intimacy? How do you suppose we do that?

134. If there’s something I can do for you, what would it be?

135. What makes our love different from other loves you experienced before?

136. If you could get me to do something I haven’t done yet, what would it be?

137. What’s something that you’ve always wanted to know that you’ve been scared to ask me?

20 Sexual Questions to Ask Your Boyfriend

Let you and your boyfriend find new ways to take your intimate life to the next level. Some moments in your relationship can do with a little bit of extra romance here and there. So, why not spice things up by asking your boyfriend some sexy questions?

Sexy Questions for Your Boyfriend

Don’t be afraid to ask him a few dirty questions that can turn even the most somber mood into something heated in and out of the bedroom. These boyfriend questions will surely bring your relationship the ultimate pleasure that will keep your guy coming back for more. 

138. What, if any, of your body parts do you like me to touch often?

139. What’s the hottest thing I could whisper in your ear at any given time, anywhere we are?

140. Ideally, how long do you think sex should last?

141. Can you tell me the difference between sex and making love, if there is any?

142. What’s your absolute sexual fantasy that you want to experience in real life?

Every guy has that ultimate bedroom fantasy. Let him share those thoughts with you, and maybe you can make his wish come true. Surely, this kind of conversation will get your intimacy fired up. 

143. Have you ever gone to a strip club before?

144. Do you love it whenever I kiss you there? 

145. If I were to give you a sexy massage right now, where would you want me to start?

146. Can you tell me the sexiest thing you think you can whisper to me in the bedroom?

147. Can you guess what I’m wearing under this dress/sweats right now?

148. What’s something about me, physical or otherwise, that turns you on straight away?

They might not all agree, but men have that switch that gets them turned on instantly. Find that out, and you’ll know how to set his world on fire ultra-fast. 

149. Do you think there are some ways we can improve our sex life? What is it, and how do you suggest we do it?

150. What’s the ultimate cuddle-up-the-sofa-worthy movie we can watch together?

151. What’s your favorite thing, giving or receiving oral sex?

152. If we can only be friends, would you want there to be benefits in our friendship?

153. If you could pick a public place where you want to do it, where would it be?

154. What do you think is the naughtiest thing we can do?

155. What sexy scene from a movie would you want us to do together?

156. Have you ever thought of filming one of our intimate moments so you can watch it again and again?

157. Do you have any secret bedroom kinks you have yet to share with me?

Why Asking Intimate Questions Is Great for Couples

Here’s the thing. As cliche as it sounds, girls like to find out things, but guys are not exactly chatting machines. Asking questions is the best in-between, a shortcut for you to learn anything you’ve been dying to know about your boyfriend and for him to share some things he might not be comfortable just blurting out, out of the blue.

Not to mention that:

It’s a fun way to get to know your boyfriend. 

Whether your relationship is a few weeks old or a few decades-long, there are always new ways to learn about your significant other. Instead of speculating or figuring things out as you go, why not cut to the chase and just ask? It will surely make a lot of stuff easier for both of you, and fewer misunderstandings too. 

It builds greater emotional intimacy in your relationship. 

There’s simply nothing better than a heart-to-heart talk with your boyfriend to bring you closer together and build the very foundation of a healthy, lasting relationship: understanding, trust, and open communication.

It opens deeper conversations. 

Relationships are hard enough; no need to make it harder by not talking. And since no relationships are perfect, having intimate conversations with your partner allows for fruitful discussions about a couple of the most important issues in your relationship. 

Final Thoughts – Questions to Ask Your Boyfriend

Although these questions are perfect to ask your boyfriend, the conversation can go both ways. Let him ask you questions too!

The most important thing is for you to enjoy the conversations with your partner and feel all the sweet feelings from it. Surely, this long list of intimacy-building questions will spark a dazzling kind of romance reminiscent of all the good things that made you fall in love in the first place.

So, what are you waiting for? Find the time as space, maybe a long car ride or a romantic date night, and dive into these questions to ask your boyfriend!