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 nights or phone calls interspersed with recurring ‘and what else…’. Besides, it’s a great way to get to know the man inside out.
Think about it, when you start dating a guy, you are inviting a new person into your life and trying to get to know them from scratch. Unless of course, you fell in love with your best friend. Even then, as a partner, you are about to discover a whole new side of them. And the best way to do that is to have conversations, sometimes deep and meaningful, sometimes a little light-hearted. The more the better.
Now if you are not the greatest conversationalist, your stock of questions to ask your boyfriend is bound to run out. Especially if you have been dating for quite a few years. That’s when you begin asking yourself, “What are some good questions to ask my boyfriend?” Your search for an answer has brought you to Bonobology, and we are here to help with this detailed rundown on funny, cute, dirty, deep, and romantic questions to ask your boyfriend and connect with him a bit more every day.
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.
From intimate questions to ask your boyfriend over text to random questions to keep the conversation going and have a good laugh with him – 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, when you still don’t know your partner well enough. To make sure you don’t end up with your foot in your mouth in your bid to strike some light conversation, try the following fun questions to ask your boyfriend:
Related Reading: 100+ Cute Nicknames To Call Your Boyfriend
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 when you are dating and a great dating conversation starter as well. Hypotheticals are a great way to get a sneak peek into a person’s deepest, darkest thoughts.
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 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 to 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.
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? A great question to ask your new boyfriend and learn his sneaky little secret.
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 when you are living together or you need a moving-in together checklist.
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. 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?
16. 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.
intimate questions to ask your boyfriend
Yes, cute lovey-dovey conversations flow like a dream at the beginning of your relationship. After the honeymoon period, every couple has to come back to the mundaneness of life. You flip the page to a new chapter and try to discover each other in a more genuine light. If you are at a similar stage in your relationship, these intimate questions to ask your boyfriend over text or in person will come in handy:
17. What is the one thing about us that you don’t like?
This one is a classic that never fails to do the trick. So, if you’re running out of romantic topics of conversation, ask him this. However, be prepared to take the answer on the chin. If you can make an effort to work through the issue, it may actually improve your relationship.
18. 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.
19. 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.
20. 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? And most importantly, is he over her completely?
21. What is the one secret you have never shared with anyone?
This question may get you a sneak peek into his deepest, darkest secrets. It is direct and opens up a chest of answers. Discover the skeletons in his closet with this upfront question.
Related Reading: 20 Things To Make Your Boyfriend Happy And Feel Loved
22. What are your views on cheating/monogamy?
Ask him about his views on faithfulness and loyalty toward a partner. This is an interesting way to get to know a guy and understand how he perceives relationships.
23. 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 important trait of a high-value man.
24. What is your best memory from your 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.
Romantic Questions To Ask Your Boyfriend
Ever wondered what was the best way to set the mood and get your boyfriend all mushy? The romantic questions to ask your boyfriend might do just that, besides helping you get to know your boyfriend a little bit better. Wasn’t that the goal all along? Let’s get into them. You can pick your top 10 to ask your new boyfriend on a romantic date night and take your intimacy game a notch higher.
25. 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.
26. What does our relationship mean to you?
Shoot this one when you are dating and you want to gauge the future of this relationship. Hearing him describe what you and the relationship mean to him can add a romantic twist to even the drabbest moments.
27. 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.
28. 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.
29. 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 romantic surprises for him.
Related Reading: What Is Consent In Dating?
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. You can truly turn up the heat with this one.
32. 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. A great time to ask this one is when you decide to meet parents and take your relationship to the next level.
Serious Questions To Ask Your Boyfriend
If you want to know your beau’s values and goals, these serious questions to ask your boyfriend will get the job done. You should definitely give these a shot before crossing a serious milestone in your relationship, like meeting the parents or getting married. By the time you’re done asking these questions, you’d know your man a lot better.
33. Do you see me in your future?
The most important of all questions to ask your boyfriend when you are dating. 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 or best friend to understand his dating history better.
35. What are your thoughts on sharing household responsibilities?
Will you be the one running errands and 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? This is an important question to ask when you are getting married or about to move in together.
36. 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.
37. 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.
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. It’s a must-ask when you are living together.
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.
42. Have you ever considered an open relationship?
One of the tricky love questions to ask your boyfriend. This can tell you where he stands. Intimate questions such as this can help you understand your SO’s 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 and let you know whether you are dating a homophobe or not.
44. How do you unwind at the end of a long day?
Once again, if you’re thinking of a long-term relationship and want to end up living together at some point, it’s important to know what his wind-down routine is. 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 when you are living together or before you get into a serious relationship. 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 about their religious beliefs. However, staunch beliefs and intolerance of divergent views on god and religion can often become a sore point between couples.
48. 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.
49. How well do you get along with your siblings?
This is the perfect question to ask your boyfriend when you are getting married. 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, especially when you are getting married soon.
52. Do you believe in destiny?
It’s important to ask this question to make sense of his beliefs and value system in totality. His views do not have to align completely with yours but knowing the answer to this question 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.
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 to get a sense of your future with him.
55. What is my one habit you can’t stand?
This is certainly one of the unique questions to ask your boyfriend when you are dating. Not all the questions have to be about him, use this as an opportunity for some healthy introspection as well.
Related Reading: 30 Sexy, Dirty Text Messages For Your Boyfriend
56. 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.
Cute Questions To Ask Your Boyfriend
These questions are perfect for when all you want to do is snuggle up next to your love and turn into a mush-ball. If you’re feeling the need for a few cuddles, these questions might help you get things off the ground.
57. 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?
58. 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.
59. 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.
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 when you decide to meet the parents or to surprise him and his family 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? 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.
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 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.
65. What do you think I admire the most in you?
This is one of those cute questions to ask your boyfriend when you are dating 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.
Related Reading: Is Your Jealous Boyfriend Being Possessive And Controlling?
67. 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.
68. 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 history and experiences. Ask him this question straight up!
69. Who is your biggest support system?
What are some good questions to ask my boyfriend, you ask? Well, ask this one and he would be so touched by your effort to know such meaningful details of his life. We all have people in our lives we lean on in times of distress. To know your boyfriend truly well, you have to know what his inner circle looks like.
70. Who was your first celebrity crush?
Remember yours? Yes, exactly. First celebrity crushes are often embarrassing and hilarious.
71. 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?
72. Which was the first dating app you signed up on?
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.
Deep Questions To Ask Your Boyfriend
Sometimes you need to get into your man’s psyche to understand him better. Who knows, you two might end up connecting on a deep level 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.
73. Are you scared of commitment?
One of the quick-fire questions to ask a man when you are dating. This is something to talk about if you’ve been together long enough and settled in the relationship, but he hasn’t made any big gestures signaling a long-term commitment.
74. 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, is a habitual user, or is completely anti-drugs. Drug addiction can be detrimental to your relationship.
75. 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 when you are getting married.
76. 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.
Related Reading: 23 FaceTime Date Ideas To Strengthen Your Bond
77. 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.
78. 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.
79. What is the one thing you can’t stand about your current place of work?
This is one of the interesting 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.
80. And the one thing you appreciate the most?
If he has laid his heart bare about 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.
81. What’s your take on how couples should split finances?
It is among the vital relationship questions to ask your boyfriend when you are living together. If you’re thinking long-term, discussing finances is crucial for avoiding differences in the future.
82. 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.
83. What’s your take on parenthood?
Yet another crucial relationship question to ask your boyfriend when you are getting married. Becoming parents is a choice and also a huge responsibility, and it’s vital that you’re both on the same page about this.
juicy questions to ask your boyfriend
Are things getting a little dull in your relationship? Are you caught in the loop of office to home and home to office? Have your conversations been reduced to discussions about the bills, grocery lists, and what series to watch next? If it sounds relatable, you can quickly scan through our list of juicy questions to ask your boyfriend to spice it up a bit and rekindle the old flame in your relationship.
84. 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.
85. 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.
86. 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.
87. What is your wildest sexual fantasy?
One of the questions to ask a guy you like is about his sexual inclinations. Ask and you may be surprised by how colorful and vivid your boyfriend’s imagination is.
88. How do you feel about showering together?
This naughty question can give you a new ritual to add to your relationship when you are living together. A damn hot one at that! You are both going to love what this leads to.
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 discover a piece of delightful information that you’re never going to forget.
89. 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.
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 infuses 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 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? This is something you could also adopt in your own lifestyle; and in case you didn’t know, couples who work out together have a better sex life.
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’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.
95. What would your dream romantic holiday look like?
It is only natural to know what your boyfriend’s expectations from vacations are. If you’re a mountain person and he loves the ocean, you’d have to figure out an arrangement that offers the best of both worlds for your next couples trip.
96. 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. Ask some follow-up questions to know him better.
97. 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.
98. 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
99. Travel the world for free or be the first settler on the moon?
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 of his 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.
FAQs
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.
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.
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.
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.
Your contribution does not constitute a charitable donation. It will allow Bonobology to continue bringing you new and up-to-date information in our pursuit of helping anyone in the world to learn how to do anything.
Ask Our Expert
You must be Logged in to ask a question.
