231 Questions to Ask Your Boyfriend

By Dumb Little Man

January 10, 2024

Boy and Girl Doing conversation with each other

Having a boyfriend is definitely one of the best feelings in the world and do you want to know what’s more fun? -it is getting to know him.

Asking your boyfriend questions enhances your relationship, causes intimacy and it’s a no-brainer in building a lasting relationship with your boyfriend. However, some of these questions should be asked with care so that your boyfriend doesn’t feel like you’re too pushy and also feels like you’re some kind of FBI.

Some boyfriends are very private and do not like a lot of digging and investigation into their personal lives. The magic to asking your boyfriend and getting the right answer is to be a good-mood reader, yes that’s right. certain questions should come upon a certain mood day. well, good to know that you should ask your boyfriend questions to help you know and relate better with your boyfriend, so what are the questions you should ask him? if you read further, then you get to unwrap the what’s, when, where, why, and how of your boyfriend.

Relationship Questions to ask your Boyfriend

Relationship Questions to ask your Boyfriend
a girl with boy

Photo: economictimes.indiatimes.com

⫸ What communication style resonates most with you in expressions of affection??

This question is not a cliché. If you get to know the love language that helps you spice things up with him.

⫸ What attracted me to you at first? 

Knowing what the first attraction was will help keep you in check so you can always stay attractive to him.

⫸ What is the one thing that excites you the most about our relationship?

Relationship questions like this one will help you keep doing the one exciting thing your boyfriend loves.

⫸When we first started dating, how long did you think it was going to last?

With the answer, he gives here, you can tell what could change about him later.

⫸ Can you describe our relationship in one word? 

this question excites you both in terms of knowing the core values of your relationship.

⫸ If you got the chance to describe our love in one word, what would it be?

Love is a tingling feeling that causes butterflies, so getting this feeling often is healthy for the relationship.

⫸ What’s your most memorable moment on the night we first met? 

Makes you feel special and knows the moments that are most memorable for both of you.

⫸ What is your greatest fear for our relationship?

Knowing his fear is not a bad thing as this helps you to be the strong link in the chain.

⫸ Have you ever felt there’s someone else you would have loved to be with?

The response to this question will help you feel secure around him and his friends.

⫸ What is that one difference in our characters that you love so much?

The response to this question will help you know how often you should display this character around you.

⫸ What is that one similarity in our characters that you love so much?

The response to this question will help you know how often you should display this character around him.

⫸ What do you think I can do to make you want to end a relationship?

This is a tricky question and mostly a triggering one for your partner who is not open to a topic like this.

⫸ What is the best thing about being in a long-term relationship?

This is quite an interesting question to ask your boyfriend to know how you both can stay connected in a long-term relationship.

⫸ What’s the worst thing about being in a long-term relationship?

The response to this question will help you avoid any kind of disconnection.

⫸ From watching your mum and dad, what do you think a relationship should look like? 

The way a guy grows up will affect his character even in relationships.

⫸ What do you consider as the most important rule in a relationship?

The response to this question is very important because it is an interesting thing to know what your boyfriend considers a major role in your relationship.

⫸ When did you realize you wanted to go into a relationship with me?

Some questions are not entirely deep questions but they are very necessary to ask.

⫸ What would you say is the best thing for me to have you as my boyfriend?

The response to this question could go a long way, it helps you have something to hold on to in a relationship.

⫸ Do you have friends with healthy relationships?

When you talk about healthy relationships, by default you both are learning how to make your relationship work.

⫸ Would you consider yourself a jealous lover?

Another important talk is knowing your boyfriend’s reaction in terms of jealousy.

⫸ To make our relationship work, what do you think we should work on the most?

The world is full of lots of solutions and recommendations for couples, but knowing the one that works for your boyfriend makes it more interesting.

⫸ What conversation do you think we should have more often?

If you ever plan on staying with him for the rest of your life then this is a must ask.

⫸ What conversation would you suggest we stop having?

The response you get to this question will make you not be tagged as a nagging girlfriend.

⫸ Would you say that I am more of a realist, pessimist, or optimist?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ If you were to change anything in our relationship, what would it be?

The response you get to this will help you know what you both need to work on in your relationship.

⫸What would you say makes our relationship unique from others?

The dynamicity of your relationship can keep you going sometimes whenever you are in doubt.

⫸ What’s your favorite TV show?

Knowing the questions to ask about TV shows helps you to know his favorite TV show which in turn helps you to bond with that show.

⫸ Do you love winter or summer?

He could choose any of the options, it’s just a fun question to ask your man.

⫸ What genre of music do you love listening to when in the bedroom?

⫸ Would you come with me if I had to travel far away?

⫸ Can you stay in a long-distance relationship with me?

The response to this would bring you both closer.

⫸ What comes to your mind when we are apart?

Getting a response like this makes a cute couple most time.

⫸ Do you believe in love at first sight?

⫸ What is your take on the word ‘soulmate’?

This makes you relate to him in some sort of way.

⫸ Have you ever thought we were made for each other?

The response to this would bring you both closer.

⫸ What movie ever made you cry?

Guys can be very emotional sometimes and they need someone to share this emotion with.

⫸ What lesson did you learn from your former relationship?

This question isn’t to stare up competition but just to know how better to relate with your man.

⫸ What does a good day mean to you?

That is definitely a guy’s favorite thing, knowing what a good day looks like.

⫸ What experience or knowledge did you think you got quite late?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ What gross thing do people do that irritates you?

⫸ What character do you have that you wish other people could have?

⫸ Is there anything you’re hard on yourself about?

Every relationship should be beneficial to one another, so knowing which area of his life he is being hard on himself can help you relieve him from overthinking things.

⫸ What do you really want from this relationship?

These are the kind of questions to ask your boyfriend early enough so you get to know his interest in the relationship.

⫸ What is your favorite song?

there is nothing in knowing your boyfriend’s favorite song.

⫸ What song do you hate the most?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ What song will you recommend to your friends?

Romantic questions to ask your boyfriend are something to look forward to because it has a way of lifting the mood of your partner.

⫸ What is your dream job?

One thing questions like this will do for you is to boost your relationship to
great heights.

⫸ What does your dream life look like?

Don’t ever feel shy about asking your man questions like this.

⫸ What is that one big thing you want to get?

⫸ How did you get to know your best friend?

One thing questions like this will do for you is to boost your relationship to great heights.

⫸ Would you get to know my friends?

The response to this question could go a long way in knowing how he will relate to your friends.

⫸ What do you think could change about us?

⫸ What are the things you wish you could do to me right now?

⫸ What is that behavior you’ve ever done for someone and told no one about?

⫸ What event traumatized you when growing up?

⫸ What turns you on the most about me?

would you choose to know what turns him on or just act vaguely in bed?

⫸ What is your favorite outfit you want to see on me?

Questions like this make life easy for both of you.

⫸ What would you do differently if you could turn back the hands of time? 

⫸ What can make you really nervous?

Getting a response to questions like this makes a cute couple most time.

⫸ Do you have a health condition you’re managing?

The response to this would bring you both closer.

⫸ Do you take Alcohol?

These are the kinds of questions to ask your partner early enough so you get to know his level of tolerance to Alcohol.

⫸ What did you do when growing up that you hid from your parents?

This makes you feel related to him in some sort of way.

⫸ Who do you know in your life who has a healthy relationship right now?

Questions like this make life easy for both of you.

⫸ What is the most stupid thing you have convinced a friend to do before?

⫸ Who makes you feel less of yourself?

These are the kind of questions to ask your partner early enough so you know his insecurities.

⫸ What relationship question would you like to ask me?

Getting responses from questions like this to make a cute couple most times

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Deep Questions to Ask Your Boyfriend

Deep Questions to ask your Boyfriend
ask ask something to his man

Photo: psychalive.org

⫸ How can you tell the weakest sign of someone?

If there is any weakness you have and you feel insecure about sharing with your partner, knowing the answer to these questions will help you act in your boyfriend’s presence.

⫸ What’s your take on fate or destiny?

This lets him know that you really want to know about him.

⫸ What are your core values?

Core values are people’s hardcore belief systems so knowing your boyfriend’s core values helps you know what you share in common.

⫸ What are your philosophies about life?

Relationship questions like this help you understand your boyfriend’s perception of life

⫸ Do you believe in the existence of God?

This is a very personal question and this will help you know your boyfriend’s Religious belief system.

⫸ What would you say is the worst thing that can happen to me for having you as a boyfriend?

You don’t want to be the sole loser in this world of varieties, you want to know your fate in a relationship as early as possible.

⫸ What would you say you’re living for?

What people live for can also be tagged as their core values.

⫸ What is the most difficult truth you have learned to accept?

When you get the response to this question, you will also get to know this difficult truth that he has chosen to accept.

⫸ What’s the number one thing on your bucket list?

The response to this question could help you know your man better.

⫸ What situation or challenge made you mature the most?

Don’t ever feel shy about asking your man questions like this.

⫸ What’s your worst nightmare?

It’s really difficult to go about life without having hiccups and nightmares here and there, so sharing these moments in conversation will help him.

⫸ What are the most incredible moments you wished you had?

Better late than never they say, if he has moments, he wished he had, he can as well have these moments with you now.

⫸ What drives your passion?

This question is mostly directed to the go-getter kind of boyfriends.

⫸ If I allowed you to date anyone, would you want to?

⫸ Do you believe there’s such a thing as ‘the right person for you?

⫸ Do you feel I’m the right person for you?

Romantic Questions to Ask Your Boyfriend

Romantic Questions to ask your Boyfriend
a boy with his girlfriend at beach

Photo: pinterest.ph

⫸ What can anyone do to become attractive to you immediately?

This is one of the romantic questions to ask your boyfriend, knowing the answer to that helps you stay attractive.

⫸ What does a perfect date look like to you?

Knowing what a perfect date looks like to your guy matters in preparing for every single date.

⫸ What time of the day would you love to go on a date?

This helps you prepare for future dates.

⫸ How would you give affection?

How your man chooses to give affection is relative to his understanding of love and love languages.

⫸ Would you describe your love for me as love at first sight?

Random but a cute question to ask.

⫸ How would you describe our first kiss?

Don’t ever feel shy about asking your man questions like this.

⫸ When did you realize you love me?

Romantic questions to ask your boyfriend are something to look forward to because it has a way of lifting the mood of your partner.

⫸ When you wake up next to me, what is your first thought?

This makes you feel related to him in some sort of way.

⫸ Where would you love to go for a honeymoon?

Getting a response to questions like this makes a cute couple most time.

⫸ What movie have you seen that reminds you of us?

If he told you the movie, he has watched that reminded him of the both of you, then it wouldn’t be a bad idea to see the movie again, but this time it should be the both of you.

⫸ When I say I love you, do you always believe me?

This question is a very cute question to ask your man just so he knows you mean your love towards him.

⫸ Would you like it if I kissed you in public?

You don’t want your man to get angry at you or feel embarrassed in public for being kissed by his girlfriend that is why it’s important to ask him what he thinks about you kissing him in public.

⫸ Would you pick PDA (public display of affection) for low-key affection?

Some guys are very low key and others love Public displays of affection, you just have to know where your man falls.

⫸ Would you ever kiss in the snow?

⫸ Where is the weirdest place you ever had sex?

⫸ Do you love to be at the top or bottom?

⫸ How would you like to be loved and shown affection?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ How would you describe our level of showing affection to each other?

When you both feel the same level of satisfaction in your love life, it makes life even easier, nobody will be forcing things on the other person.

⫸ What was your first impression of me when we first started dating?

A random question, but it is also important to know this so you can carry yourself better in public.

⫸ When last did you go to a strip club? 

Romantic questions to ask your boyfriend are something to look forward to because it has a way of lifting the mood of your partner.

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Flirty Questions to Ask Your Boyfriend

Flirty Questions to ask your Boyfriend
boy too close with her partner

Photo: charleneeckstein.com

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

⫸ How would you express our first kiss?

Don’t ever feel shy about asking your man questions like this.

⫸ If you could go back in time, how would you want your first kiss to look like?

⫸ What physical feature of me is your favorite?

⫸ What do you imagine or dream of when you close your eyes kissing me?

⫸ Do you love to cuddle?

⫸ Would rather kiss for one minute or spend time with me all day?

⫸ Would you want a 5 seconds kiss or a 10-minute hug?

Romantic questions to ask your boyfriend are something to look forward to because it has a way of lifting the mood of your partner.

⫸ Do you think you can kiss me in public?

⫸ How frequently do you think of sex?

Romantic questions to ask your boyfriend are something to look forward to because it has a way of lifting the mood of your partner.

⫸What is your favorite sex position?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ What part of your body do you like being touched the most?

⫸ What time of the day are you sexually active?

Romantic questions to ask your boyfriend are something to look forward to because it has a way of lifting the mood of your partner.

⫸ Do you prefer big breasts or big butts?

This question is not so you feel secure or insecure around him, it’s just to kill time and also know his preferences.

Salient Questions to Ask Your Boyfriend

Salient Questions to ask your Boyfriend
girl touches boy hand

Photo: cosmopolitan.com

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⫸ What are your expectations for your old age?

If you’re planning to spend the rest of your life with him, then you should share your expectations.

⫸ In your family, who do you consider the closest?

Don’t ever feel shy about asking your man questions like this.

⫸ Would it be okay if you met my parents?

This makes you relate to him in some sort of way.

⫸ How would you express your relationship with your parent?

A guy cannot live independently of his childhood, so getting to know this

⫸ Do you think you got equal treatment same as your siblings when growing up?

⫸ What is the one thing that annoys people about you?

what annoys people about him might not piss you too.

⫸ Would you say that there is a health problem that runs in your family?

The response to this would bring you both closer.

⫸ What is the nicest thing you’ve ever done for somebody?

This is a casual question, but your man might just want to talk about it so he can get some accolades from his girlfriend.

⫸ What’s the nicest thing anyone has done for you?

⫸ How often should we go on a date in a week?

Dates are very essential in any relationship and can help spice things up.

⫸ Would you say you’re close to your extended family?

These are the kinds of questions to ask your boyfriend early enough so that you know his stand with his extended family.

⫸ How would you express the kind of student that you were? 

⫸ What was your most memorable moment as a child?

The response to this would bring you both closer.

⫸What do you think about having pets around?

These are the kinds of questions to ask your partner early enough so that you know his take on pets.

⫸ What are your hobbies?

Getting to know your man’s hobbies will help you to decide the fun thing to do when you’re both together.

⫸ How would you describe your parents’ relationship with each other?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ Where are you from?

This is a must-ask question if you love him and want to spend the rest of your life with him.

⫸ How many places have you lived, name them.

This is quite a fun question to ask, knowing this will help you know his favorite place he has ever lived.

⫸ Where is your favorite place to cool off?

There is nothing in knowing your boyfriend’s favorite place
for cooling off.

⫸ Would you choose to be the power over money?

This is one of the fun questions to ask your partner.

⫸ What occupations do you think robots could replace?

These are the kinds of questions to ask your partner early enough so that you know his take on robots and technology generally.

⫸ If you could switch careers, what would be your new career?

⫸ What should an ideal family look like?

⫸ What do you love most about your family?

This will help you know your man in person.

⫸ Would you go back and change anything in your past?

A cute question to ask on a random day.

⫸ Would you choose fame over fortune?

He could choose any of the options, it’s just a fun question to ask your man.

⫸ Would you consider yourself a positive impact maker?

One thing questions like this will do for you is to boost your relationship to great heights.

⫸ Can you suggest one thing that can be implemented by the government to improve the lives of the citizens?

⫸ What are the girlish things you did?

This makes you relate to him in some sort of way.

⫸ What is the most masculine thing you’ve ever done?

⫸ What’s your take on feminism?

These are the kinds of questions to ask your boyfriend early enough so that you know his take on feminism.

⫸ If you were to choose one place to live in, where will it be?

⫸ What triggers your anger?

The response to this question could help you know your man better.

⫸ What was your favorite subject in school?

knowing his favorite subject might give you a hint about what he loves to do or talk about.

⫸ What would you say was your worst mistake that later had a positive outcome?

⫸ If money wasn’t a problem, where would you live?

⫸ Can you remember your first toxic experience with anyone?

⫸ What were the names of the first two books you ever read?

⫸ Apart from money what other thing can get your rapt attention?

Many times, guys tend to only focus on money and making a lot of them, so getting his response for this question will help you know your man better.

⫸ What’s your greatest fear about your future?

Getting a response like this makes a cute couple most time.

⫸ What creepy thing do you do on a regular?

Don’t ever feel shy about asking your man questions like this.

Personal Questions to Ask Your Boyfriend

Personal Questions to ask your Boyfriend
Girl and Boy talking with together

Photo: shutterstock.com

⫸ What makes you unique from other guys?

His uniqueness helps you to recognize his abilities.

⫸ What is that thing you tried so hard at but just didn’t get right?

⫸ What is your best memory about your parent raising you?

Undoubtedly, you both come from different backgrounds, so getting to know about his best childhood memory helps you understand where he is coming from.

⫸ What do you think people over-rate about you?

The answer to this question will help you to see the level where your boyfriend is on that overrated skill or ability.

⫸ Which of your parent do you think you are more like?

This is just an interesting question to ask.

⫸ What is the most incredible moment you missed out on?

⫸ What do you think people under-rate about you?

The answer to this question will help you to see the level where your boyfriend is on that underrated skill or ability. And this also helps you not to underrate his ability in that area.

⫸ At what moment do you think you’ve gotten to your breaking point?

Knowing your boyfriend’s breakpoint moment helps you pay attention to details and be around for him in his downtime.

⫸ What are your temperaments?

This is a major question to ask your boyfriend because temperament for our personality, and knowing them early saves you from stress.

⫸ What is the highest thing you do when you get really angry?

Though this is not a romantic question the answer to that question will help you ease your boyfriend when he is angry.

⫸ What do you think the role of a woman is?

It is very important to ask your boyfriend questions like this, this is not one of those fun questions to ask but will definitely help you know how your boyfriend sees women.

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Funny Questions to Ask Your Boyfriend

Funny Questions to ask your Boyfriend
laughter session of a boy with her partner

Photo: freakingtech.com

⫸ Do you prefer to do your laundry by yourself or no movies for a month, which will choose?

⫸ What Mundane activity have you Mastered so well?

⫸ What’s your wildest conversation with a lady?

⫸ Favorite Movie you’ve ever seen?

there is nothing in knowing your boyfriend’s favorite movie.

⫸ Does your brain get on autopilot too often?

These are the kind of questions to ask your boyfriend early enough so you get to know how his brain functions sometimes.

⫸ If you were to sing a song on your wedding day, which one would it be?

⫸ What song trend do you hate?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ Would you rather be the President for a day or take a million dollars?

Everyone would rather throw a question that suggests multiple options for your boyfriend to pick from and this will make the relationship fun.

⫸ What would you change if you were the President for a day?

⫸ If you were to be a superhero, who would it be?

Questions like this make life easy for both of you.

⫸ If you had power, what would you do with it?

The response to this question could help you know your man better.

⫸ What do you think are the advantages and disadvantages of
social media?

⫸ Do you think social media should be scrapped?

⫸ What if I get pregnant for you, how will you react?

The response to this question could help you know your man better.

⫸ Can you remember the last time you made a fool of yourself?

This will help you know your man in person.

⫸ What will a room filled with your fears look like?

These are the kinds of questions to ask your boyfriend early enough so that you know what his fears and insecurities are.

⫸ Describe yourself in three words.

⫸ Would you pick a fancy nice car over saving an old criminal from drowning?

⫸ What are your worst days like?

You definitely don’t want to be a part of your man’s worst day, so getting to know his worst days will not be harmful.

⫸ What is the favorite thing you love most in this world?

This will help you know your man in person.

⫸ If your life were a sport, what sport would it be?

Questions like this make life easy for both of you.

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Cute Questions to Ask Your Boyfriend

Cute Questions to ask your BoyfriendPhoto: blog.motifphotos.com

⫸ Tell me that one thing you should do but will never do.

This question helps you not to get pushy on him on things he never wants to do, you don’t want to be tagged as nagging.

⫸ What’s the happiest you’ve ever gotten?

This is not a personal question so there is no harm in asking it.

⫸ What non-sexual activity do we do together that you love the most?

knowing his favorite thing about you to keep the relationship spiced up.

⫸ Who is your favorite football player?

Girls tend to love soccer because of their boyfriends but make the mistake of mixing footballers’ names up in the future.

⫸ Which football club is your favorite?

It is interesting to know his favorite club, with this, you can pick another club so you have a bit of argument about football, guys love it a lot.

⫸ Watching soccer or wrestling?

This will help you know your guy better.

⫸ What would you like to talk about?

This is a random question but guess but, it works like magic in helping you have deep conversations.

⫸ Do you ever wish I could read your mind?

Some questions are very random but they are very spicy for a relationship.

⫸ What makes you think I am the right person for you?

Don’t ever feel shy about asking your man questions like this.

⫸ What flaw do I have that you ironically love the most?

⫸ What’s the number one secret you always wanted to tell me but haven’t?

This can be fun especially if asked in a truth or dare manner.

⫸ What is the behavior you’ve ever done and told no one?

⫸ Who is your celebrity crush?

Don’t ever feel shy about asking your man questions like this.

⫸ What do you wish you could be better at?

⫸ Which fictional hero made you fall in love with them?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ If you were to be a bird, which would it be?

⫸ Would you ever go farming in your free days?

Romantic questions like this help to boost your partner’s confidence and trust around you.

⫸ Who holds the most significant place in your circle of friends?

⫸ Which movie would you enjoy seeing with friends?

⫸ Which friend do you perceive as the most friendly?

Don’t ever feel shy about asking your man questions like this.

Here are some simple questions to ask your Boyfriend

  • Movies or TV shows?
  • Coffee or Tea?
  • Hip-hop or rap?
  • Video games or computer games?
  • Money or Love?
  • Truth or dare?
  • Twitter or Instagram?
  • Call or text messages?
  • Money or fame?
  • Books or Magazines?
  • Sleep with light or without light?
  • Junk food or real food?
  • Cinema or Netflix at home?
  • Android or IOS
  • comedy or drama?

Conclusion

If you have read this far, then you’re on a train to build a healthy, long-lasting relationship with your Boyfriend. What you choose to do with some of the responses you get from your man is very important. Some of these questions are very confidential to him and you might just keep the conversation between the both of you and bridle your tongue when you’re with your girlfriends. Good luck with your relationship.

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