100 Questions To Ask Your Boyfriend

Questions to ask your boyfriend

Imagine if you always had some smart, funny, interesting questions to ask your boyfriend. You’d never run out of things to talk about. The right questions at the right moment can truly make conversations flow for hours on end. This means no more boring date night or phone calls interspersed with recurring ‘and what else…’. Besides, it’s a great way to get to know the man inside out.

This detailed rundown on funny, cute, dirty, deep and romantic questions to ask your boyfriend has you covered.

100 Questions To Ask Your Boyfriend

Table of Contents

Have you always wanted to know more about your boyfriend’s past but don’t know how to broach the topic? Knowing the right questions to ask your boyfriend about his ex can do the trick. Similarly, if you’ve wanted to give dirty talking a chance but are too shy to make the first move, dirty questions to ask your boyfriend can come to your rescue.

This compilation of 100 questions to ask your boyfriend covers every such eventuality. Let’s start with a popular sub-category first, the fun questions to ask your boyfriend.

Fun Questions To Ask Your Boyfriend

No matter how funny you two are or how well you two connect with each other, there will come a time when you’re both awkwardly silent, thinking about what to say. Especially during the beginning of a relationship, where you’re not really sure what your partner’s sense of humor is like. To make sure you don’t have to worry about that much, the following list of fun questions to ask your boyfriend will do the trick:

1. If you had a get out of jail free card, what would you use it for?

Certainly, one of the most fun questions to ask your boyfriend. Hypotheticals are a great way to get a sneak peek into a person’s deepest, darkest thoughts. You’ll learn things about him that you could not imagine learning otherwise. They often prove to be great conversation starters too.

2. Have you ever drunk texted a wrong number?

A classic funny question to ask your boyfriend. Did he ever send a text bitching about his boss to the boss? Or a message that was meant for his ex to his mom?

3. What do you imagine you’d win a big award for?

Would it be the Nobel or the Pulitzer or an Academy Award? Or is he a Grammy’s kind of guy? It is one of the fun questions to ask your boyfriend that will give you a sense of his secret aspirations and dreams.

4. How would you react if a guy asked your number at a bar?

This is definitely one of the funny questions to ask your boyfriend that will lead to some equally funny responses. He may even have an anecdote or two to share.

5. What’s the grossest thing you’ve done?

One of the more unique questions to ask your boyfriend, this will incite some laughs. This question is equal parts funny and freaky. Be prepared to listen to some rather unpleasant details.

6. If you could be a vegetable, which one would you be?

Not everything you ask him has to be serious and deep. These funny questions to ask your boyfriend can really liven up the mood.

7. What is the weirdest situation you have ever walked into?

Parents making out, a sibling caught in the act, someone undressing…we’ve all had our share of weird moments in our lives. Asking your man about his definitely qualifies as one of the funny questions to ask your boyfriend. It’ll lead to some hilarious revelations.

8. What is your spirit animal?

This is one of the more fun questions to ask your boyfriend casually. Quirky questions such as these always come in handy when you want to lighten up the vibe of the conversation.

9. If a movie was made about our love story, what title would you pick for it?

Just another random and fun question to ask your boyfriend. His response might just take you by total surprise. This is one of the questions to ask a guy you like in order to know whether he likes you too!

10. Which is the one show you can binge-watch over and over again?

Friends or Seinfeld? Game of Thrones or Grey’s Anatomy? Star Trek or Westworld? Find out where his allegiances lie.

11. What is your guilty pleasure?

Is he a guy who loves to watch sitcoms or rom coms when he is by himself? Or listens to love songs when he has his earphones on?

Related Reading: What to do after a fight with your boyfriend?

12. What is the one thing you can’t leave the house without?

Want to find out whether he is a low-maintenance guy or not? This question will reveal the answer, loud and clear. Trust us, you want to know this one.

13. Did you think our relationship would last when we first started dating?

Want some freaky questions to ask your boyfriend? Make sure you add this one to the list and watch your guy squirm with uncertainty at how to respond to this one.

14. What was your favorite TV show as a child?

Ask him about his pop-culture preferences. This may sound like one of the more casual questions to ask your boyfriend but if you’re both more or less the same age, it can give you a new territory to bond over.

15. Do you prefer cats or dogs?

This is yet another essential question to ask your boyfriend in the getting to know each other phase. The cats or dogs or no pets at all preferences can often prove to be relationship deal breakers, especially if one of you is an ardent animal lover.

Fun questions to ask your boyfriend
Fun questions to ask your boyfriend might just annoy him

16. What is the one pet name you’re embarrassed of?

The key here is to mix things up. What better way to do that than asking him about his embarrassing pet names. It gives you the perfect arsenal to playfully annoy your boyfriend.

Romantic Questions To Ask Your Boyfriend

Ever wanted to ask your boyfriend to set the mood, maybe? The romantic questions to ask your boyfriend might do just that, as well as enabling you to get to know your boyfriend a little bit better. Wasn’t that the goal all along? Let’s get into them.

17. What physical trait do you admire the most in me?

This is just the right mix of flirty and naughty and will make his thoughts wander to that one part of you he just can’t get enough of.

18. What is the one thing I do in bed that blows your mind?

If you’re feeling particularly naughty, ask him this. We promise one thing will lead to another.

19. What is your best sexual memory of us?

Been having a bit of a dry spell? Such dirty questions to ask your boyfriend can totally steam things up between you two. How to know your lover lies in understanding what he likes. This question is important for you to know the same.

20. What does our relationship mean to you?

Hearing him describe what you and the relationship mean to him can add a romantic twist on even the drabbest moments.

21. What is the one thing that I do for you that you cherish the most?

When thinking of romantic topics to talk about with your boyfriend, ask him what he appreciates most among all things big and small that you do for him and your relationship.

22. What would your dream romantic holiday look like?

As a couple, you’d be taking trips together. It is only natural to know what your boyfriend’s expectations from these vacations are. If you’re a mountain person and he loves the sea, you’d have to figure out an arrangement that offers the best of both worlds.

23. What is the one life experience you want to have with me?

This is among the romantic questions to ask your boyfriend that can open up a whole new world of possibilities for you as a couple.

24. What is your idea of a romantic evening?

Now, this is one of the perfect romantic questions to ask your boyfriend right when you start dating. You’ll know what to expect from your date nights in the future and it’ll come in handy in planning those romantic surprises for him.

25. Do you prefer me kissing your neck or nibbling your earlobe?

With such dirty questions to ask your boyfriend, you can really turn up the sexual heat between you two.

26. What is your wildest sexual fantasy?

One of the questions to ask a guy you like is about his sexual inclinations. Ask and you’ll be surprised about how colorful and vivid your boyfriend’s imagination is.

27. How do you feel about showering together?

This naughty question can give you a new ritual to add to your relationship. A damn hot one at that! You are both going to love what happens after this one.

28. What is the one thing about us that you absolutely love?

This one is a classic that never fails to do the trick. So, if you’re running out of romantic topics to talk about with your boyfriend, ask him this. The answer will probably make you smile with glee!

Related Reading: What Is Consent In Dating?

29. What was your first sexual experience like?

Looking for intimate questions that will help bring you closer to your boyfriend? This is it. As long as he is comfortable talking about it, ask him for details about who, when, where, and most importantly, how it made him feel. Asking about the first sexual encounter gives you the perfect opening to bring some dirty questions to ask your boyfriend into play.

30. What turns you on?

This is certainly one of the fun and romantic questions to ask your boyfriend. Start with a basic one about his turn-ons.

31. Is something about me turning you on right now?

If you want to bring on some zesty energy, this is one of the questions to ask a guy you like. Then, you can turn the heat up by bringing him to the present. Even if he wasn’t turned on until now, this question ought to do the trick.

Serious Questions To Ask Your Boyfriend

For when you really need to know the values and goals your beau has, these serious questions to ask your boyfriend will get the job done. By the time you’re done asking these questions, you might just come out of it knowing your man a lot better.

32. If you had the option, would you date other people?

You can find out how committed he is to you and your relationship with this single question. Dating has its intricacies and asking such questions may clearly bring out how he truly feels about them.

33. Do you see me in your future?

The most important of all questions to ask your boyfriend. His readiness or reluctance to answer this one is enough to tell you all you need to know about your future with him.

34. Have you ever been attracted to a friend?

This question becomes particularly pertinent if there is a special female friend in his life that he is too close to. This is one of the questions to ask your boyfriend about his ex to understand his dating history better.

35. What are your thoughts on sharing household responsibilities?

Will you be the one running errands, doing chores while pursuing a career? Or is he on board with the idea of doing the dishes, taking out the trash, cooking an occasional meal or fixing breakfast every morning?

36. What’s one thing you absolutely love about us?

When he tells you what he doesn’t like about the relationship, it’s bound to sting a little. This is the perfect antidote to your previous question. It’ll prevent any negative emotions from spiraling out of control.

37. What is your best sexual memory with a partner other than me?

Feeling naughty and adventurous? Ask him about his sexual escapades from the past in detail. It will also open up the possibility of more questions to ask your boyfriend about his ex.

38. Are you an adventure enthusiast?

You have to know the answer to this question before you become too emotionally invested in your boyfriend. If he’s an adrenaline junkie and you’re not or vice-versa, co-existing can become a nightmare.

39. Do you have any addictions?

This is definitely not a question to ask on the first few dates, but if you start seeing each other officially, you have the right to know about your partner’s vices and addictions.

Related Reading: 10 Questions Every Girl Should Ask A Boy Before An Arranged Marriage

40. What, according to you, is the best way to resolve a fight?

Every couple has its share of disagreements and fights. That’s why this is definitely one of the relationship questions to ask your boyfriend.

41. Have you ever cheated in a relationship?

Another one of those freaky questions to ask your boyfriend that he’ll struggle to answer. But you know it has been on your mind, so just go ahead and ask away. These tricky love questions always bring out interesting responses.

42. Have you ever considered an open relationship?

One of the tricky love questions to ask your boyfriend would be this one. This can seriously tell you where he stands. Intimate questions such as this can help you understand their take on romantic relationships.

43. What’s your take on gay relationships?

Speaking of beliefs, it is vital to understand how liberal or conservative your partner is. This is one of those questions that will spill the beans without fail. Now, they don’t necessarily have to be a champion of LGBTQ rights but you have to be sure they’re not with a homophobe either.

44. How do you unwind at the end of a long day?

Once again, if you’re thinking long-term and want to end up living together at some point, it’s important to know what his wind-down routine is like. If you like to curl up with a book and he prefers to blast the music, it can be a recipe for disaster.

45. What’s your take on porn?

We have for you yet another freaky question to ask your boyfriend. Now that you’re romantically involved, you have the right to know these intimate details.

46. Would you expect me to watch it with you?

Depending on your take on the whole concept of pornography, this can either be a dirty question to ask your boyfriend or something that can trigger a full-blown debate. But ask you must to know what potentially awaits you in the future.

47. What are your views on religion?

Not all partners have to be on the same page in terms of their religious beliefs. However, staunch beliefs and intolerance of divergent views on god and religion can often become a sore point between couples.

48. What is your best memory from childhood days?

If you’re still in the initial days of dating and getting to know each other better, ask him this to get some insight into what growing up was like for your man. After all, our childhood experiences do have an impact on our adult personalities.

49. How well do you get along with your siblings?

This is the perfect follow-up to family-related questions to ask your boyfriend. Also, immensely essential, if you’re both thinking long-term. Knowing the kind of bond he shares with his siblings and family will help you prepare yourself for the kind of interactions you can expect to have with them in the future.

50. What’s your idea of sound financial planning?

This also becomes one of the vital relationship questions to ask your boyfriend, especially if you’re at the threshold of taking the next step.

51. Are you in debt?

Laying your cards on the table about your financial health is vital for the health of your relationship. If your partner is not forthcoming on that account, don’t hesitate to ask.

52. Do you believe in destiny?

How to know your lover is all about asking him the right questions. It’s important to ask this question to make sense of his beliefs and value system in totality. They do not have to align completely with yours but this is necessary to understand him better.

53. What is the one thing you and I don’t have in common?

Sure, you have your own take on your commonalities and differences, but it’s always interesting to get a fresh perspective on things. Even more so when that perspective is your boyfriend’s.

romantic questions to ask your boyfriend
Serious questions will lead to a healthier bond

54. What is your retirement plan for yourself?

When discussing life possibilities, take a no holds barred approach. It’ll give you an insight into what growing old with this man would look like. This question is not just important to know him, but also for you.

55. What is my one habit you can’t stand?

This is certainly one of the unique questions to ask your boyfriend. Not all the questions have to be about him, use this as an opportunity for some healthy introspection as well.

56. If you could change one thing about us, what would it be?

This is one of those relationship questions to ask your boyfriend that can help you figure out the problem areas and work on fixing them. Tread carefully and do not get paranoid at his honest answers.

Related Reading: 30 Sexy, Dirty Text Messages For Your Boyfriend

57. Is there an ex you still think about?

With questions to ask your boyfriend about his ex, make sure you keep an open mind and don’t take offense. The idea here is to fortify your bond with your boyfriend and not create a reason for a rift.

After all, most of us have that one ex – the one that got away – that we tend to think about every now and again.

58. Have you kept any souvenirs from your past relationship?

A jacket, a letter, perfume, an old t-shirt – so many people have relics from their past lingering around. Does your boyfriend have them too? Ask and you shall find out.

Cute Questions To Ask Your Boyfriend

For when all you want to do is snuggle up next to your love and ask him the cutest questions that make you go “aww!”. If you’re feeling the need for a few cuddles, these questions might help you get things off the ground.

59. Which fictional character would you dump me for?

Yes, this qualifies as a freaky question to ask your boyfriend. But then, what’s the harm in a little harmless banter?

60. Do you prefer kisses or hugs?

What is his preferred act of showing and receiving affection? Be sure to shower him with whichever he chooses. That way he’ll know that these questions you ask him aren’t just for the heck of it.

61. What is the one thing your mother cooks that you can’t have enough of?

Cookies, cakes, pies or stew…every family has a go-to recipe that they cannot get enough of. What is your boyfriend’s? You could use this information to your advantage and surprise him with this favorite meal on some special occasion.

62. How would you describe an ideal wedding?

Inching toward the big day? Or just know you will walk down the aisle with this man waiting at the other end? Ask him what his idea of an ideal wedding is. Would he prefer an intimate ceremony or a big wedding? Does he like banquets or open arrangements? Often weddings become too bride-centric while the groom becomes a sidekick.

Remember that it is the most important day of his life too, so factor in his preferences. And keep them in mind, if and when you plan the wedding.

63. How would you describe your first crush?

If your last question made the vibe too intense, lighten up the mood with cute questions to ask your boyfriend such as this. The first crush is a pleasant memory for most people.

64. What attracted you to me?

This is one of those cute questions to ask your boyfriend that also borders on romantic. You probably already know the answer, but hey, it’s a whole other experience to hear it from the horse’s mouth.

65. What do you think I admire the most in you?

This is one of those cute questions to ask your boyfriend that borders on flattery. But hey, what’s romance without it. Add a little mush to the mix for a heady concoction.

66. When did you realize you were in love with me?

Whether you’re celebrating an anniversary or just talking late into the night, this is one of those romantic and cute questions to ask your boyfriend that will always hit the nail on the head. Your question will take him back to that moment in time when he first realized he was falling in love and those warm, fuzzy feelings will come gushing to the forefront.

67. What was your first impression of me?

On a date night and can’t think of what to talk about next? Such curious questions to ask your boyfriend can take you on a trip down memory lane.

68. How have you dealt with heartbreak?

This is one of the intimate questions that will make you see his vulnerable side. Did he cry himself to sleep on many nights? Was there binge drinking and drunk calling involved? And most importantly, is he over her completely?

69. Do you cry easily?

Men have been taught to toughen up and put up a tough exterior for centuries. If your boyfriend can cry, it means he has embraced his soft side and emotional vulnerabilities. That’s an amazing trait to have in your man.

70. Who is your biggest support system?

We all have people in our lives we lean on in times of distress. To know your boyfriend fully well, you have to know what his inner circle looks like.

71. Who was your first celebrity crush?

Remember yours? Yes, exactly. First celebrity crushes are often embarrassing and hilarious.

72. What is the weirdest fashion trend you followed to a T?

Overalls, leather pants, weird hairdos, gel-laden hair…what was the one raging fashion trend from the past that your boyfriend embraced wholeheartedly and now wants to erase the memory of completely. There’s a good chance there is photographic evidence of these sojourns. Find them and you’ll double over with laughter.

73. What’s happening in this Instagram post?

Open his Instagram account and ask him about the story behind the most quirky or offbeat post you can find. But do not make it sound like you are always stalking him online.

74. What is the last item on your Google search history?

While you’re at it, ask him about his last Google search. We bet something interesting will come up and you will open up a range of things to talk about.

75. Which was the first dating app you signed up on?

cute questions to ask your boyfriend
Ask him cute questions over texts

Is he a Tinder guy or does he prefer Bumble or OkCupid? His taste in dating apps can tell you a lot about his preferences.

76. What was the worst date you had via a dating app?

Dating apps and disastrous date experiences go hand in hand. Ask him about his. How to know your lover is all about knowing his histories and experiences. Ask him this question straight up!

Deep Questions To Ask Your Boyfriend

Sometimes you need to get into the psyche of your man’s mind to try and understand him better than you do. Who knows, you two might end up connecting on the deepest of levels and you might realize you’ve just come across your soulmate. Even if you don’t end up discovering a soulmate connection, at least the deep questions to ask your boyfriend will help you understand how his mind works.

Related Reading: Is Your Jealous Boyfriend Being Possessive And Controlling?

77. Are you scared of commitment?

One of the quick-fire questions to ask a man would be this one. This is something to talk about if you’ve been together long enough, settled in the relationship, but he hasn’t made any big gestures signaling a long-term commitment.

78. Have you ever done drugs?

If you’re looking for freaky questions to ask your boyfriend, this one cannot be left out. Besides, it’s important to know if he’s tried drugs for the sake of experience or is a habitual user or someone who’s completely anti-drugs. Drug addiction can be detrimental to your relationship.

79. What are your views on cheating/monogamy?

Ask him his views on faithfulness in relationships. This is an interesting way to get to know a guy and understand how and what he feels about dating and its facets.

80. How do you deal with confrontation?

Is he the confront the uncomfortable kind of guy or someone who prefers to bottle up feelings? You have to find out, and that’s why this is one of the essential deep questions to ask your boyfriend.

81. What is the one secret you have never shared with anyone?

To really get to know his deepest, darkest secrets, this question is the one. It is direct and opens up a chest of answers. Discover the skeletons in his closet with this upfront question.

82. What keeps you up at night?

Another one of those intimate questions that will help you understand your boyfriend on a deeper level, as you gain a sneak-peek into his fears and insecurities.

83. How would you define love?

Yet another of those deep questions to ask your boyfriend that will help you understand your man a little better. It’s also a great way to assess if you’d be compatible in the long run.

84. If you got a do-over, what would change about your life?

This is one of those deep questions to ask your boyfriend that will give a clear insight into your man’s sense of achievements and regrets in life.

85. What is the one thing you can’t stand about your current place of work?

This is one of the questions to ask a guy you like. Job satisfaction and a sense of professional fulfillment are vital for a person’s peace of mind. If your boyfriend is struggling on that front, it could impact your relationship too.

86. And the one thing you appreciate the most?

If he has laid his heart bare on everything unbearable about his workplace, follow it up with this question to get a complete sense of how he views his professional life as a whole.

87. What’s your take on how couples should split finances?

It is among the vital relationship questions to ask your boyfriend. If you’re thinking long-term, discussing finances is crucial for avoiding differences in the future.

88. Can you keep secrets?

This is one of the deep questions to ask your boyfriend, as his answer can convey a lot about his outlook on life.

89. What’s your take on parenthood?

Yet another crucial relationship question to ask your boyfriend. Becoming parents is a choice and also a huge responsibility, so you must be both on the same page about this.

Random Questions To Ask Your Boyfriend

Ever in the mood to just ask your beau the silliest things? The random questions might just help you come across a piece of delightful information that you’re never going to forget. After all, the random questions to ask your boyfriend are what really keep the boredom at bay, so let’s get right into them.

90. Would you like to live in the city or the suburbs?

Everyone has a vision for their adult life. As partners, you and your boyfriend should discuss what your individual visions are to make sure you can coexist in harmony.

91. What makes you feel alive?

A good workout session, reading a book, being one with nature…what is the one thing that infused life in every pore of his being? To really understand your boyfriend and who he is as a person, this question is necessary.

92. What’s your go-to drink?

Find out if he is a beer guy or a scotch lover so that you can stock up appropriately whenever he visits your place.

93. What is your biggest pet peeve?

For inexplicable reasons, certain things drive us all up the wall. The thing about pet peeves is that they’re as diverse as they come. For someone, it could be traffic snarls, and for another, it could be sudden screeching sounds. Find out what’s his.

94. What is your go-to workout routine?

This is just a casual question to ask your boyfriend to learn more about his lifestyle. Is he someone who loves running outdoors or pumping iron at the gym? Or does working out not feature in his routine?

95. What is the one conspiracy you believe in?

Does he believe the moon landing was a farce or that the CIA was behind JFK’s assassination? This question can lead to some intriguing revelations. Do some follow-up questions to know him better.

96. If you could pick a superpower, what would it be?

Haven’t we all entertained this question from time to time? So, ask what your boyfriend’s preferred superpower would be and compare notes. Together you can embark on a fantastical journey, imagining how you two would club your powers to save the world.

97. What’s the one food that everyone loves but you can’t stand?

Does he think pancakes are overrated? Or does he hate Nutella? Time to challenge some popular opinions. Maybe follow up with some of your own, and brace yourself for some passionate arguments.

Related Reading: Dealing With An Insecure Boyfriend? Here Are 15 Coping Tips

98. How do you think we complement each other?

Does he think you’re the yin to his yang? Or that you’re two peas in a pod? Discover how he views your companionship and compatibility.

99. Travel the world for free or be the first settler on the moon?

Random questions to ask your boyfriend
Where would you travel with your boyfriend?

His answer will tell you a lot about whether he is a realist or a dreamer.

100. What makes you the happiest?

Bring out the child in him and enjoy exploring this new side to this personality. This question is extremely important to truly understand somebody and their needs in life.

The 100 questions will hold you in good stead for a long time to come. So keep them handy! By the time you are done with these, you both will have reached that comfort level where the conversation just flows.


1. How can I know my boyfriend better?

To really know and understand your boyfriend better, you must ask him lots of questions. In relationships, there often are not any right or wrong questions. It’s all about the timing. Ask him some of the questions above to get started on getting to know him well.

2. How do I start a romantic conversation with my boyfriend?

You can ask him about what he likes about you or what is the one thing of yours that he cannot live without. Ask him how he feels every time he sees you. To sizzle things up further, you can ask him about his sexual fantasies and what he likes in bed.

3. What are some questions to ask your boyfriend to see if he knows you?

You can test him on random trivia about yourself. Ask him if he knows your favorite animal, your first pet’s name, your favorite ice cream topping, and cute little details like that.

4. What are some silly questions to ask your boyfriend?

Ask him questions about his fandoms like what fictional character would he want to date. You can also ask him about his pet peeves or his guilty pleasures.

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