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500+ Questions to Ask your Boyfriend

500+ Questions to Ask your Boyfriend

Updated on Oct 20, 2022

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

500+ Questions to Ask your Boyfriend

So… you are looking for Questions to ask your boyfriend

Then my guess is… you have surpassed the “honeymoon phase” of your relationship.

I mean, when you first start dating someone, there’s a strong desire to know each other and a lot of topics to talk about. You can spend hours talking to each other and it still seems less.

A few months in and the “spark” slowly starts to fade… and the conversations turn boring.

That’s the time when you need to turn it around and put some real effort to keep the relationship alive… because no matter how long you have been with your partner, the mantra to a happy and healthy relationship is: Never ending, deep, long and riveting talks.

The good-ol’ “How was your day?” might serve the purpose, sometimes but it’s definitely not enough to spark meaningful conversation.

So, here’s a pre-prepared list of 500 questions (yes, FIVE HUNDRED!) to ensure that you never run out of words.

500+ Questions to Ask your Boyfriend
500 Questions to ask your boyfriend

So, let’s first begin with…

Fun questions to ask your boyfriend

Laughter is the best medicine… oh yes, it very well is.

No matter what the problem is, if you can make your partner laugh, you can pretty much find the solution to everything there is.

But sometimes, it gets very hard to spark laughter even if you are the funniest person in the room. In such cases, you can use these funny questions to ask your BF (Boyfriend) and savor the smile on his face.

I bet, it’s your favorite view! 😉

  1. Which moments of your life do you cherish the most?
  2. Who is your role model in life and why?
  3. What is your favorite ride at an amusement park?
  4. Does your brain ever go on autopilot mode?
  5. Do you think aliens exist?
  6. What would be the name of a website made on you?
  7. Is there any inedible thing you ever want to eat?
  8. Have you ever danced on top of a bar?
  9. What is a fun slogan to define your career/job?
  10. Have you ever tried a gross drink because of a dare?
  11. What do you think the color blue would taste like?
  12. Tell me some embarrassing moments from your high school?
  13. If you had all the money in the world, what would you do first?
  14. What is the craziest thing you ever googled?
  15. Do you have a go-to lame joke to dodge awkward conversations?
  16. Will you ever accept the power to be invisible?
  17. Which is your dream name to have?
  18. If you could switch genders, what will you do first after the switch?
  19. Which is your favorite travel music song?
  20. If you were a part of a cult, what would it be?

Now that you both have shared a good laugh, it’s time to get crazy with some…

Freaky questions to ask your boyfriend

A relationship definitely needs communication but it also needs some fun, some crazy. In Fact, a lot of crazy! (if you know what I mean! :P)

So, if you think your conversations have been running dry for quite a while, make some efforts to bring back the lost spark. Crazy conversations are as important as deep conversations.

If all your efforts to trigger a stupid conversation are going in vain, try these fun dirty questions – trust me, they will do exactly what they are supposed to do! 😉

  1. Have you ever had a freak accident?
  2. Can you make a conspiracy theory on spot?
  3. Weirdest place that you have urinated at?
  4. How many ants would it take to cover an entire elephant?
  5. If water wasn’t called water, what would it be called?
  6. Have you ever imagined a world filled with male copies of you?
  7. Have you ever wished to be thrown into a bucket of chocolate sauce?
  8. Which mad scientist experiment do you wish to do if you had zero constraints?
  9. What is the most horrendous brand name you can think of?
  10. Do you believe in magical beings?
  11. Have you ever seen a white horse?
  12. How often do you check out your naked body in the mirror?
  13. Do you enjoy taking nude photos just for fun?
  14. Have you ever sent naked pictures to someone by mistake?
  15. Do you loathe doing house chores?
  16. What is the weird cleanliness obsession that you have?
  17. What is illegal in reality but feels legal in your head?
  18. If you could make a new car, which is the most unique feature it would have?
  19. If you could launch a candle product chain, which unique scent would it be known for?
  20. If someone let you put something on a billboard, what would you put?

After some laughter and fun, let’s dive deep with some…

Deep questions to ask your boyfriend

Even though you have been with him for a long time now, there are some layers that still remain hidden and you definitely want to uncover them.

So, whether you have just started dating or have been with him for years, these questions will help you discover strange things about him.

Be careful while asking these questions, you don’t want to overwhelm him by being too intrusive!

  1. What is the one thing you learned a little too late?
  2. Has there ever been a time when you were too hard on yourself?
  3. How often do you feel yourself wearing down?
  4. What was your favorite thing about the way your parents raised you?
  5. When was the last time you cried?
  6. Which is your happiest memory?
  7. What is your go-to choice, mind or body?
  8. Which is the one thing you’ll regret for the rest of your life?
  9. Do you think one can have too many favorite memories?
  10. What has been the lowest point in your life?
  11. Have you ever dreamt of a goal and given up on it?
  12. Which has been your biggest achievement to date?
  13. What do you think is the best part of human nature?
  14. What is your one memorable life miracle?
  15. How do you think would people remember you?
  16. Have you ever broken someone else’s heart?
  17. Do you think happiness is permanent?
  18. Does one earn happiness or it simply happens?
  19. Do you think crime can ever be erased?
  20. Do you love being around kids?

This conversation is sure to put you both in a serious mood and there’s a possibility that you forget the “love” in between.

So, here are some

Sexual questions to ask your boyfriend

Amidst a deep conversation, you also need some “sexy” fun and these questions will give you exactly that.

We all know sometimes, words can do what actions cannot. But that’s only possible when you have the right set of questions handy.

Remember, it’s very easy to crossover the thin line and makes the conversation cheap. If you don’t want that, ask these questions but don’t forget the grace!

  1. Are you a quick or a long sexual make out person?
  2. What is the kinkiest naughty stuff you have done?
  3. How many sexual positions have you tried?
  4. What do you prefer to wear to bed with me?
  5. How often do you think dirty talk should happen?
  6. Do you want to see any part of my body right now?
  7. Can we play strip poker?
  8. How many layers of clothes do you love seeing me in?
  9. Can I lick a part of your body when you have your eyes closed?
  10. Do you think it is time for an intimate moment in our relationship?
  11. What would you do to me if I was chained on the bed?
  12. Do you enjoy going rough or slow?
  13. Do you enjoy sexting?
  14. Have you ever done it on a video call?
  15. What is your favorite body part to be kissed at?
  16. Do you enjoy tearing my clothes at the moment?
  17. Which is your favorite sexual position?
  18. How would you rank your top five favorite body parts?
  19. Which color underwear do you love seeing me in?
  20. Do you think live-in relationships are all about sexual bonding?

I am sure you are feeling wet and maybe… had a good time! (I mean! :P)

But sex can’t replace the butterflies you will feel when you ask these

Cute questions to ask your boyfriend

In the hustle-bustle of daily life, most couples forget to communicate love. This is your golden chance to revive that opportunity.

This list of cute questions will not only allow you to confess all that you feel for your man but also push him to say all that he has been hiding all this while.

Of course, that otherwise “cold” face has a heart warmer than you can imagine.

  1. Do you like to spend time cuddling?
  2. What was your first thought after we started dating?
  3. Do you think online dating would have worked between us?
  4. What would you describe me as a dessert?
  5. Who is the first person you talk to after a bad day?
  6. How often do you feel like talking to me in a day?
  7. Do you think we trust each other?
  8. What qualities make a couple last?
  9. What is something you could never have enough of?
  10. Do you enjoy spending the holidays with your partner?
  11. Are you a secret bathroom singer?
  12. Who are your top three people you would easily cheat on me with?
  13. How many times did you think about asking me out before actually doing it?
  14. Are you comfortable in this relationship?
  15. Do you enjoy having cooking Sundays with me?
  16. Would you ever be jealous if I meet my ex?
  17. What is your favorite scent?
  18. What is your favorite outfit for a girl?
  19. What would you say in your last five minutes with me?
  20. Do you have faith in destiny?

Oh, now stop gushing girl. 😛

And take the conversation forward with some…

Dirty questions to ask your boyfriend

Now that he has told you all the cute things you wanted to hear; I can see the love overflowing in your eyes.

So, why not take it to the bed… I mean, not straight away but you can ofcourse set the mood with these questions.

Trust me, what follows after will make it all worth it! 😉

  1. Have you ever had a naughty dream about me?
  2. What sexy movie scene would you want to recreate with me?
  3. Have you ever had a fantasy about someone else while dating me?
  4. What is your biggest turn on?
  5. Which has been the most erotic place that you’ve done it in?
  6. Have you ever tried doing it in a public washroom?
  7. What is the sexiest thing on your bucket list?
  8. Do you like it when I touch your back?
  9. Are you a virgin?
  10. Which color lingerie do you love on me?
  11. What is your favorite roleplay story?
  12. What was the best orgasm before dating me?
  13. Have you ever faked an orgasm?
  14. Will you go skinny dipping with me?
  15. Which is your favorite kind of porn?
  16. Have you ever thought about making a sex tape?
  17. Do you read erotic fanfiction to enjoy?
  18. Do you like to spank me in bed?
  19. How high is your sexual drive?
  20. How many times can you do it in one night?

After some intimate moments with your partner, I am sure you both need a little breather.

These questions will give you exactly that.

Good questions to ask your boyfriend

After a rough day at work, when your guy comes back home: all he needs is your arms and a light and fun conversation.

At this time, it will not be right to choke him with deep intimidating questions or even try to spark intimacy. Give him the space he needs while also discussing what happened through the day.

Or ask a few questions from this list!

  1. What is your favorite childhood memory?
  2. What makes you different from others?
  3. Which is your favorite memory from college?
  4. If you were to enter into a solo dance competition, which dance style would you choose?
  5. Which is your favorite song?
  6. What is your favorite poem?
  7. What is the funniest incident you have ever been a part of?
  8. If you could choose to have dinner with any two people in the world, who would they be?
  9. Are you grabbing the last slice of pizza-person?
  10. Have you ever had a ‘drop the mic’ moment?
  11. Are you healthy food or a junk food person?
  12. Do you like coffee over tea?
  13. How was your day at work?
  14. Has your boss been mean to you before?
  15. Do you think you have good co-workers?
  16. Do you prefer running or going to the gym?
  17. How aware are you of feminism?
  18. Have you ever tried bungee jumping?
  19. What was your dream job as a kid?
  20. Do you ever want to be an entrepreneur?

You love your man immensely, but sometimes just saying “I love you” is not enough.

So, bring back the romance in a new fashion with the help of these…

Romantic questions to ask your boyfriend

After all, what’s a relationship without some good-old romance, right?

Every girl dreams about her man going down on his knees and saying “Will you be mine?”. But don’t you think your man deserves some romance too? And you have been to too many traditional date-nights…

So, instead, add a modern touch to your “romantics” attempts and ask him these questions:

  1. What will be your definition of a perfect day with me?
  2. Where would we go next for a romantic dinner?
  3. Have you ever been on a perfect date?
  4. Do you believe in true love?
  5. How often do you agree when people say that love at first sight exists?
  6. Do you think, ‘forever love’ exists?
  7. What would be ‘our song’ in your head?
  8. Do you prefer a long hug or a warm kiss?
  9. Do you think we both have been vulnerable enough in our relationship?
  10. What is your meaning of a ‘right person’ for you?
  11. Do you want to have a grand wedding or a small cute one?
  12. Do you think a couple (we) should always balance each other?
  13. Do opposites always attract?
  14. Are you an affectionate person?
  15. What is the best thing about being in a relationship?
  16. What is the worst thing about being in a relationship?
  17. Which is your favorite pick up line to use on me?
  18. Can you stay 24 hours without talking to me?
  19. Will you try to make a long-distance relationship work or not?
  20. What is the most precious thing you’ve learned after being with me?

All that said and done.

You don’t want to forget the purpose of asking these questions: to get to know him. So, when you get the chance, dive deep into him with these…

Serious questions to ask your boyfriend

Your boyfriend had a life before you came into the picture.

He had his own interests, passion, hobbies, traumas, dreams, career goals, and everything else. But most guys fail to show the troubling part of the life he spent without you.

These questions will help you uncover that!

But make sure, you don’t make him feel targeted and empathize with him when he is opening up to you.

  1. What makes you nervous?
  2. Which is your biggest fear in life?
  3. Have you ever had only sexual partners and not relationships?
  4. Do any health problems genetically run in your family?
  5. Has your family ever had any bias against girls?
  6. Do you ever feel left out at parties?
  7. Do you believe in afterbirth?
  8. Have you ever volunteered for the needy?
  9. Do you donate to charity?
  10. Do you believe in only forgiving or forgetting as well?
  11. If your house was on fire, what were the top 5 things you would grab first?
  12. If given a chance to choose between your best friend and girlfriend, who will you choose?
  13. Will you ever want to be famous?
  14. How often do you feel the burden of life on your shoulders?
  15. Would you sacrifice all your life earnings for a stranger?
  16. Would you ever jump in front of a bus to save a friend?
  17. Have you ever had a friend who was terminally ill?
  18. If you had a crystal ball to tell you any truth you wanted to know, what would you look for?
  19. When was the last time somebody told you it will all be okay?
  20. Which childhood tradition have you put in extra effort to maintain even today?

Wufff! That was some serious conversation out there.

It’s time to lighten it with some…

Flirty questions to ask your boyfriend

Healthy flirting is important – yes, even with your boyfriend!

But the age-old “What are you doing, sexy?” has become stale. You need new ways to tell your guy that he still makes you weak in the knees like he used to.

These questions will help you learn new ways to flirt while also stirring conversations.

  1. Do you enjoy watching me touch you?
  2. Do you ever want to be a part of the mile-high club?
  3. How was our first kiss in your mind?
  4. Have you ever played cupid for a friend?
  5. Would you kiss me on my forehead every day?
  6. Do you enjoy waking up next to me?
  7. Do you enjoy doing PDA?
  8. What makes you laugh after a bad day?
  9. Which place in the city is your secret escape?
  10. What would be our couple’s Halloween costume?
  11. If you had the choice to suggest a new skill, what would it be?
  12. Have you ever guessed what my idea of an ideal date is?
  13. Do you like kissing in the rain?
  14. Which physical feature of mine you can’t resist?
  15. Do you like holding hands?
  16. Do you ever wish to take a shower with me?
  17. Do you like kissing my neck?
  18. How will you define me, cute or pretty?
  19. Do you ever want to make out on the dance floor?
  20. Will you ever sit with me under the stars and listen to warm music?

Oh, did he just blush? I am sure he did!

So why not turn it into an adorable smile with these

Cute flirty questions to ask your boyfriend

You can flirt in two ways: sexy or cute… while sexy flirting can lead you to action, cute flirting can make their heart smile.

Don’t believe me? Try asking these questions and you will be amazed to see his eyes brimming with love for you.

Oh girl, just pick one and get started!

  1. Who is your forever lovable fictional character?
  2. If you could be immortal, what will you do first?
  3. Do you like it when I make the first move?
  4. Does loving in real life mean the world to you?
  5. Do you ever let me win games on purpose?
  6. I hate arguing with you, do you hate it too?
  7. What do I do often that makes you blush?
  8. Do you think you know what women crave?
  9. Are you a chocolate-with-strawberry person?
  10. Do you like Netflix and chill?
  11. What is your favorite thing to come back home to?
  12. When do you let your guard down in a relationship?
  13. What is the most outrageous thing you can do for your partner?
  14. Will you ever choose not to spend a day with me?
  15. When was the last time you felt butterflies in your stomach?
  16. How often do you take a break from romance?
  17. Do you think romance is only about sex and passion?
  18. How often have you laughed when you saw me sleep talk?
  19. Do you think I get flustered around you?
  20. Can you ever beat me in using horrific pickup lines?

No. No. Don’t stop there.

It’s just the time to ask these…

Intimate questions to ask your boyfriend

Now that “Love is in the air”, you certainly don’t want it to end the conversation there.

Well, it’s not easy to start an intimate conversation but if you are committed to it and have a list of intimate questions to ask your partner ready – it is not so difficult either.

But remember, intimacy is of two kinds: physical intimacy and emotional intimacy. There’s nothing wrong with either but you need to choose the direction you are headed and accordingly ask questions.

  1. What is important in a relationship according to you?
  2. How many times do you think someone can fall in love in a lifetime?
  3. Do you think relationships should always be full disclosure?
  4. Have you ever been in an open relationship?
  5. Have you ever been betrayed by a close friend?
  6. Do you think money can make you happy?
  7. Have you ever thought about gay rights?
  8. Do you think relationships can work after a partner cheats?
  9. How is your relationship with your parents?
  10. Which childhood game would you cherish the most, all your life?
  11. Which is your deal-breaker when it comes to friendship?
  12. Have you ever received a gift that made you cry?
  13. Is emotional connectivity more important than physical attraction?
  14. Do you keep a positive outlook in life or a neutral stance?
  15. Do you think hatred can drive success?
  16. How often do you remember someone from your past who walked away?
  17. What is the best gift you’ve ever received?
  18. What is my biggest pet peeve that you tolerate?
  19. How many unchecked items do you have on your bucket list?
  20. Have you ever faced a hard truth that you can’t forget?

If you chose physical intimacy, I bet you need some…

Sexy questions to ask your boyfriend

If you both have been dating quite a while, you already know each other’s weaknesses in bed. So, why not make use of it? 😉

I mean, to crank up the heat and have some real fun in bed!

Imagine the chills on his bone when you ask him “What will you do if I bite your neck right now?” [secretly knowing that “neck” is one of his erogenous zones!].

Excited? Then, what are you waiting for?

  1. What are your thoughts on sex toys?
  2. Is there anything you want me to try right now?
  3. Have you ever had a sexual fantasy that wasn’t completed?
  4. Have you ever invented a sexy game in your head?
  5. What will you tell me right now if I ask you to talk dirty to me?
  6. What is your idea of a satisfying sexual experience?
  7. Have you ever complimented the body of a 30-year-old?
  8. Do you ever dream about recreating dream sex sequences from tv shows?
  9. What do you think about santa naught foreplay?
  10. Can you unhook my bra with one hand?
  11. Do you want to decide what I’ll wear tonight?
  12. Are you a sexually shy guy?
  13. Where is your favorite hookup spot in town?
  14. Do you think I look hot in yoga pants?
  15. Do you enjoy sex or making love?
  16. Do you want to give me love bites?
  17. What does my body taste like?
  18. What will you do if I send you a dirty photo of me right now?
  19. Have you ever craved my lips when we didn’t meet for days?
  20. Do you ever dream of me answering the door without any clothes on?

Ah, I know you are tired! Ahem… Ahem…

So, lie down next to him and continue with these…

Questions to ask your boyfriend about you

You definitely want to know how much your guy knows about you. I mean, who doesn’t!

We all love it when he can complete your sentence without you having to say it… or communicate your thoughts without you having to implicate it.

But guys can’t always tell you how much they know you without you asking them about it. So why not?

  1. Do you think I am a fan of date nights?
  2. What did you think of me, the first time we met?
  3. What is the one similarity between us that you appreciate?
  4. Have you ever lied to me to protect me from being hurt?
  5. Do you have any secrets, yet to tell me?
  6. Have you ever thought about introducing me to your family?
  7. Would you ever call me your soulmate?
  8. Have you ever judged me for a habit or insecurity?
  9. Why do you still want to be with me?
  10. Do you think I am excessively possessive?
  11. Which nickname would you rename me with, if given a chance?
  12. Do you think I have anything I need to improve on?
  13. Do you remember our first picture ever taken together?
  14. Have you ever had any issues with my friends and not told me about it?
  15. What do you think are my thoughts on marriage?
  16. Where do you think I stand in my career?
  17. Do you ever compare yourself to me or my friends?
  18. What can I be a snob about?
  19. Do you think I am comfortable around your friends?
  20. Have you ever wondered about breaking up with me?

By now, you are either happy by the fact that he knows you so well or disappointed that he fails to notice the tiny things that you do in daily life.

Either way, don’t stop talking!

Random questions to ask your boyfriend

On occasions when you are tired and have nothing to talk about, random questions prove to the best rescue.

A “Do you think other planets have lives?” is a lot better than complete silence. It at least reflects the effort you take to keep the conversation going.

So, ask away my girl!

  1. If money was never an issue, where would you live?
  2. Which were the last two books you’ve read?
  3. What is the one thing you know you have to do but ignore?
  4. What do you look forward to doing when you are old?
  5. What is the one thing you tried to master but just could not?
  6. Are you a call or a text message person?
  7. Which is your favorite meal on a holiday?
  8. What is your favorite movie scene from the 2000s?
  9. Which is your favorite cartoon character?
  10. What is your must-have product on your nightstand?
  11. Which era in history do you want to try to live in?
  12. Have you ever dreamed of being a superhero?
  13. Do you wish to ever get lost in the woods?
  14. Which is your favorite way to waste time every day?
  15. Do you think heaven and hell exist?
  16. How often have you dreamed of traveling to space?
  17. Do you think old age was better than the current times?
  18. Have you ever wondered what being a parent is like?
  19. Do you believe in the existence of ghosts?
  20. If you could be someone else for a day, who would it be?

Now that you both have enough of shilly-shally, it’s time for some weird fun.

Weird questions to ask your boyfriend

Sanity is boring. Extremely boring.

You need some absurdity even in a romantic relationship. You need to talk about things that can make you wonder “Why the hell am I laughing at it?”

Well, yes! That’s the fun of being weird and trust me, it really is fun!

  1. Which is the most unhygienic thing people do that creeps you out?
  2. What habit of yours do you think is rare in others?
  3. Have you ever puked at a pub?
  4. Have you ever had a stranger phone call you to shout?
  5. Do you ever go into your room and then forget why you went there in the first place?
  6. Which animal would you love to fight against?
  7. Which is your biggest fear when it comes to your friends?
  8. Which is the coolest looking tree you can imagine?
  9. Which is the weirdest ice-cream topping you wish to try?
  10. What would be the one line you would say to the entire country if given a chance?
  11. Do you think wars should be abolished forever?
  12. How often do you wonder if fishes have necks?
  13. Do boys always call their muscles ‘guns’?
  14. What do you think is the best organ in your body?
  15. Have you ever thought of using makeup?
  16. Do you watch chick flicks as your secret guilty pleasure?
  17. What is worse, yellow teeth or yellow nails?
  18. What is the one thing you wish people couldn’t see?
  19. Do you have any unwritten life rules in your head?
  20. Are you a soup or a cereal person?

I am sure your stomach is hurting with that crazy conversation.

So, let’s get back to the grind with some…

Personal questions to ask your boyfriend

Every person has so many shades. You can’t always know everything even though you have been spending quality time with each other.

So, here’s a list of personal questions that will help you understand him a lot better and allow you to bond on a deeper level.

Be careful that you don’t touch a thread that is very much inside the circle.

  1. What will be your absolute perfect day with your family?
  2. What do you observe as the biggest sign of weakness in a person?
  3. What is the one thing you wish you had tried to learn?
  4. Do you fear the future and what it holds?
  5. What can make you angry, easily and quickly?
  6. What would your funeral be like in your imagination?
  7. What is the worst thing that has ever happened to you because you made an error?
  8. What would be the name of a book made on your life?
  9. What would be the name of the chapter in your life story based on our journey together?
  10. What will you write on your tombstone if given a chance?
  11. What will you be like if you were given a chance to change your appearance?
  12. How fascinated are you by nature?
  13. How often do you talk to yourself about yourself?
  14. Do you have adamant opinions?
  15. When have you felt the loneliest?
  16. Who is the one person that makes you highly uncomfortable?
  17. Who do you value the most in your life?
  18. Which three words would you choose to describe yourself?
  19. What do you want out of life after five years?
  20. If you could be the first person to achieve something, what will you achieve?

Personal questions can be very intriguing.

So, before you swamp him with too many questions, give him some space and explore your relationship that you have nurtured so dearly all these years…  

Relationship questions to ask your boyfriend

Both of you have been putting equal efforts to nurture this relationship into something beautiful. But that doesn’t mean, both of you have the same opinions, views, or concerns about it.

So, it’s vital to know what your partner thinks about this partnership.

It shouldn’t be like, while you are day-dreaming about your future together, your boyfriend is still not ready for it.

  1. What do you think when you look into my eyes?
  2. If you could describe us in three words, what would you say?
  3. Would you ever want to go on a picnic with me?
  4. What is the one quirk that you love about me?
  5. Would you ever like it if I write a song about you?
  6. Do you find saying ‘I love you’ difficult?
  7. Are you a pro-choice or a pro-life individual?
  8. Do you think you act like a snob at times?
  9. Do you think you are nurturing enough?
  10. Are you a laid-back person or an adventurous soul?
  11. Have you ever been obsessed with something for a long time?
  12. Have you ever sneaked out of your house for a date?
  13. Do you think romantic comedy movies are underrated?
  14. What are the habits in others that annoy you the most?
  15. Which habit of yours do you think annoys me the most?
  16. What are your secret and most useful stress buster activity?
  17. Do you prefer materialistic gifts or emotional gestures?
  18. Have you ever been in a toxic relationship?
  19. Do you think the best way to move on is to wait for a long time?
  20. Which one secret you’ve regretted telling me about?

Now that you are clear about the way ahead, let’s make it entertaining with some…

Truth or dare questions to ask your boyfriend

Truth or dare, by definition, is just a game. But you have no idea the kind of information it can give you about a person.

…only if you know the right questions to ask.

If played right, it can help you uncover things you never imagined. But that’s the case only with “truth” – what about dare? Well, choose some fun dares so that you both can also enjoy alongside knowing each other.

  1. Who did you last creep on, on social media?
  2. Do you stalk your ex on social media?
  3. What is the longest time that you have ever slept?
  4. Have you ever tried to beat a world record?
  5. Can you talk in a British accent till the next turn?
  6. Which famous person do I remind you of?
  7. Who are you the most jealous of, in this room?
  8. Can you gulp down a raw egg in 30 seconds?
  9. Who will give you a wedgie in this room?
  10. Who will you challenge in a pushup battle if you wanted to lose?
  11. Get ready to empty a bottle of cold water on your head?
  12. Have you ever created an imaginary friend?
  13. Do you have a secret fake email ID?
  14. Who will you choose between your parents and why?
  15. Have you ever stolen something?
  16. How often did you bunk classes in college?
  17. Do you have a foot fetish?
  18. Do you still take power naps during work hours?
  19. Have you ever stood someone up on a date?
  20. What is the shortest amount of time that you have dated someone?

Had fun?

So, now take it forward with some

Interesting questions to ask

It’s difficult to strike interesting conversations, especially when you know so much about each other.

But if you don’t make an effort, it’s sure to suck the life out of your relationship, so before it can do that, it’s time for you to take the sword and hit it with these questions.

  1. What was surprisingly the best mistake you made?
  2. If you had a chance to go on a road trip right now, where would you go?
  3. What is the kindest thing you have ever done?
  4. If you ever had a remote control for a machine, which machine would it be?
  5. Which is the most idiotic thing that you love doing?
  6. What has been the most adorable thing someone has ever told you when they were drunk?
  7. What is the most useless subject in college?
  8. Would you choose to leave an impact on your family or on the entire world?
  9. Which old school tv show do you absolutely love?
  10. When have you had a lot of fun at work?
  11. Which invention do you think is useless for humans?
  12. Have you ever dreamed of owning a zoo?
  13. How do you feel about scientifically grown food?
  14. Do you ever want to try gardening?
  15. When do you always agree to splurge on yourself?
  16. Do you let people fight their own battles or always jump in?
  17. Are you a panicky person at times of a crisis?
  18. Movie you’ve chosen if you had a chance to act in it?
  19. Do you consider yourself an introvert or an extrovert?
  20. Which greeting do you prefer using when someone calls you and why?

Meaningful conversations can trigger different feelings: good, bad, or even both. So, I am sure you are experiencing mixed emotions.

But amidst that mess, why not give it a twist with some…

Juicy questions to ask your BF

Sometimes, you don’t want sex but just enjoy the thrill of talking about it. Neither of us can deny, the “tease” is (sometimes) more sexy!

However, people mostly fail to draw the line and succumb to the “tease.” But these naughty questions will help prevent that and also crank up the heat.

But make sure when and where you ask these questions! 😉

How often do you think about us when you are alone?

  1. Which day has been the most memorable orgasm of our time?
  2. Do you like taking your time or going in quickly?
  3. Have you ever been seduced?
  4. Do you prefer me in thongs?
  5. Which sexy song do you need to be in the zone?
  6. Do you like lacy bras?
  7. Have you ever been a part of 7 minutes in heaven?
  8. Do you like her blonde or brunette?
  9. Trying tantric sex ever came to your mind?
  10. Couple sexy yoga retreats are common, wanna go?
  11. Have you ever done it while being drunk?
  12. Were you ever able to do it in the backseat of a car?
  13. How many girlfriends have you done it with before me?
  14. What are you least attracted to about me?
  15. Do you want me to roleplay a nurse or a police officer tonight?
  16. Hottest thing you can say in bed?
  17. Will you enjoy having sex on a beach?
  18. Can you unzip my dress only with your mouth?
  19. How are you so sexy and drool-worthy?
  20. What is the favorite physical part of your body?

But, wait.

Don’t stop there… keep it going with these

Kinky questions to ask

Everyone has their own kinks or fetishes. But there are only so many people who talk about it.

But as a partner, you definitely want to know all sides of your boyfriend, no matter how weird or strange it is.

While you both laugh at the silly kinks of each other, make sure you don’t make each other feel uncomfortable.

  1. Which is your most favorite part of my body?
  2. Have you ever had a dirty dream?
  3. Do you ever want to try edible underwear?
  4. Are you a boob or a butt guy?
  5. Have you ever licked your tongue while staring at my chest?
  6. How often do you get horny after watching kinky porn?
  7. Do you enjoy BDSM?
  8. Do you enjoy me in tight jeans or a peek-a-boo skirt?
  9. Do you like to play music while doing it?
  10. Would you be a part of Santa’s naughty list this year?
  11. Will you call yourself the Hulk when in bed?
  12. Do you like to be on top or on the bottom?
  13. Do you like going down at the start itself?
  14. Do you enjoy when I am loud in bed, repeating your name?
  15. Would you want me to give you a massage with a happy ending?
  16. Do you enjoy strip teasing and lap dances?
  17. Do you like watching me touch myself on video calls?
  18. What have you named your package down there?
  19. Which is your weirdest fetish?
  20. Are you submissive during sex?

So much fun, right?

But what about the times when you come back home and don’t have the leisure to meet for the next week?

Don’t worry. We’ve got you. Here are some…

Great questions to ask over text

Texting is entirely different than an in-person conversation. Similarly, questions to ask in an in-person conversation are entirely different than questions to text.

If you want to avoid the one-word answers like yes, no, okay, maybe – you need to know the questions you should ask a guy over text.

To help you with that, here’s a pre-prepared list for you.

  1. Which movie was so upsetting that you’ll never watch it again?
  2. Which book has been your most favorite experience?
  3. Are you in touch with your extended family?
  4. What mundane task have you become an expert in?
  5. Is there a sound that scares you?
  6. What is the one thing you always hide from your parents?
  7. Have you ever considered yourself clever as a child?
  8. What is the best wi-fi name you can come up with?
  9. How many selfies do you take every day?
  10. Do you like sneaking in cute pictures of your friends and family?
  11. What is your favorite sport?
  12. Have you ever taken part in a sports tournament?
  13. Do you think you can live without your phone for a week?
  14. Which song is the most played on your Spotify?
  15. Have you ever done a movie marathon with friends?
  16. What is your favorite meme ever?
  17. Have you figured out your true emoji love?
  18. What is the one food which can give you a million calories but you’ll still have it?
  19. Have you ever lost a phone?
  20. Favorite random trivia you can come up with instantly?

Now that you have got the texting game on-point, why not step out of your comfort zone, and move on to…

Dangerous Questions to ask

Playing inside the circle is definitely comforting but not fun. If you want to discover new things about your partner, be courageous enough to ask these questions.

Remember, as the head says: it can be extremely dangerous. So, make sure, you ask them carefully.

Assess your partner’s mood before you ask these questions. It can be extremely intimidating and must be asked when both of your headspaces are calm and composed.

  1. What is the meanest thing you have ever done to someone?
  2. Have you ever felt like you did a less manly thing in your personal life?
  3. Have you ever had a friend with benefits?
  4. Have you ever faced sexual trauma in your childhood?
  5. Have you ever dumped someone via texting?
  6. Which is your ugliest dream?
  7. Are you okay with adopting kids?
  8. Do you think emotional abuse exists?
  9. Have you ever been scared of commitment?
  10. Have you ever wondered about your sexuality?
  11. Are you happy with your sex life?
  12. What are your views on divorce?
  13. What is the worst injury you have ever had?
  14. Have you ever taken a shortcut in life and regretted it?
  15. What are your views on politics?
  16. Is there anything you hate to joke about?
  17. Can you ever choose between God and fate?
  18. Have you ever been wrongly touched as a child?
  19. Have you ever been with older women?
  20. Have you ever been a part of a physical fight?

All this while, you had a mood to play along. But there are still some questions that are important to ask yet remain unclassified. So, here are some…

Important Questions to ask your BF

There can be many questions in your heart that you want to ask.

This is the time when you can set them free and just ask without giving it a second thought. No matter how silly or intriguing it is, there’s no harm in seeking answers from your partner.   

Here are some questions that I think should be discussed.

  1. What makes you angrier than most things?
  2. What has been the biggest learning from your past relationship?
  3. What is the one thing people always overestimate about you?
  4. Do you think we can ever adopt a pet together?
  5. What advice would you give to your 16-year old self?
  6. Do you think I get overdramatic at times?
  7. How upset do you get when I come back home late from work?
  8. Do you think only a girl should do household chores post marriage?
  9. Which world problem do you think is the most important one?
  10. Have you ever solo traveled?
  11. Do your friends ever bitch about me?
  12. When was the first time you felt like you were in love?
  13. Who has been your biggest crush ever?
  14. Do you think investing money is important?
  15. Do you prefer a desk job over an on-field task?
  16. Where would you draw the line between dedication and overworking?
  17. Would ever take a sabbatical from work?
  18. What kind of school would you want your kids studying at?
  19. Do you secretly like to be pampered?
  20. Will you ever think of getting a tattoo based on our bond?

In the end, here are…

5 Questions to NEVER ask your boyfriend

Now that you know everything that you should ask your boyfriend, let me tell you what you shouldn’t.

Remember, if it’s important to know the questions to ask your BF (Boyfriend), it is equally important to know what you should not ask.

So, please read ahead!

1. Why can’t you just relax?

Asking anyone this question shows your rude and impatient nature. Everyone deals with crisis differently and your job is to be there for your boyfriend, not judge him. Men are kind souls who never show their vulnerable sides. If he is being real in front of you, don’t force him into hiding again.

2. Why are you always at fault?

This question often slips out during fights or arguments. Remember, you need both hands for a clap. He is probably equally investing in the relationship but your arrogant questions are tiresome. Don’t let me walk away by blame games and ego battles.

3. Am I better than your ex?

Cue insecurity and trust issues. This question can create a drift in your bond. Don’t ever compare yourself with your partner’s ex and never let him think about it. Breakups are difficult, so cherish what you have rather than delving into the past.

4. Are you lying to me right now?

Long term relationships work on understanding and honesty. Continuously asking your party if he is telling the truth builds in a lack of connection. If he is on your side, you should support him too. Sometimes, giving a little space is also needed!

5. Do I look fat?

Asking these questions put him in an awkward spot. He loves you for who you are and will never pass a verdict on your body. This question puts you as a person with lower self-esteem. Men can never answer this question right, so it is better you forget about it!

Over to you…


That was a long list.

It might not all be relevant for you… so pick and choose, but don’t stop.

Now go make reservations for your long-due date night and don’t forget to keep this list handy! 😉

All the best!