250+ Deep And Interesting Questions To Ask Your Boyfriend

Asking your boyfriend the right questions can help you understand him better.

Written by Ratika Pai Ratika Pai
Last Updated on
Deep And Interesting Questions To Ask Your Boyfriend

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Whether your relationship is new or has seasoned with time, there will always be something more to know about him. While there can be several questions to ask your boyfriend, selecting the right one does the trick. These questions can help you know him better and make your relationship strong. Besides, it will give him a chance to open up on parts of his life that he has still not shown you.

So, if you are looking for some questions to ask your boyfriend, we have got you covered. We bring you a list of interesting questions to ask your boyfriend to have some fun time together.

251 Questions To Ask Your Boyfriend

Random Questions To Ask Your Boyfriend

You can start with some simple random questions and then go for serious ones.

  1. If you were to live alone on an island for the next three months, what are the three things you would carry with you?
  1. Did you ever have a crush on a fictional character?
  1. Have you ever felt afraid of sleeping alone after watching a horror movie?
  1. Do you have a secret talent?
  1. If you were a historical character, which one would you be?
  1. Have you ever woken up in the middle of the night and felt confused about who and where you are?
  1. Ever experienced a déjà vu moment?
  1. If you could dwell in a fictional universe, which one would it be?
  1. Have you ever done something scary to prove that you weren’t scared of it?
  1. If you could go back in time and change something in your life, what would it be?
  1. Have you ever tried to invent something new?
  1. Have you ever faked an accent to look cool?
  1. If you could date a male celebrity, who would it be?
  1. Do you believe in any superstitions?
  1. If you were granted a superpower for a day, what would it be, and what would you do with it?
  1. If you could play one sport your entire life, which sport would you choose?
  1. Pick one: money or talent.
  1. If you were to get endless amounts of money in a lifetime, would you still work for yourself or chill with the luxuries bestowed upon you?
  1. Imagine that I am a genie and am granting you three wishes. What would your wishes be?
  1. If you could time travel, would you go in the past and witness a historical event or go into the future and see what happens in the next few years?
  1. You have just found a magic carpet that can take you anywhere in the world. Which place would you visit first and why?
  1. If you were stuck in an elevator with three celebrities, who would they be? And what would you ask them?
  1. What theme song would you like to have for yourself?
  1. If you could eat one dish every day, without fearing any health consequence, which food would that be?
  1. What title would you like your autobiography to have?
  1. Pick one: pizza or hotdog.
  1. Which is your dream car or vehicle?
  1. Have you ever had a dream about someone consistently?
  1. What is the best place for a date night?
  1. What is your most effective pickup line?
  1. What do you find most attractive in a woman?
  1. What makes you fall for a woman?
  1. When was the last time you felt nervous with a woman?
  1. If I come over right now, what would you cook for me?
  1. How do you deal with female attention?
  1. Do you enjoy my company? Why?
  1. What is your idea of an ideal proposal?

Romantic Questions To Ask Your Boyfriend

It is your chance to ask him some romantic questions to know what he feels for you. You can know what you probably have been dying to hear.

  1. Who was your first crush?
  1. Whom did you kiss first, and how was it?
  1. Have you ever been heartbroken?
  1. Have you ever lied to me?
  1. Describe our first kiss in five or fewer words.
  1. What did you first notice about me?
  1. What did you feel when you first saw me?
  1. When did you first realize you feel ‘something’ for me?
  1. How do you feel when I am not around?
  1. If we were to get married, how good a wife do you think I would make?
  1. How many children would you like to have in the future?
  1. What do you like more, kissing me or hugging me?
  1. What do you like best about me?
  1. If given an option, would you like to meet me sooner in life or later? Why?
  1. Who do you think is more loving in our relationship?
  1. If we were to be a fictional romantic couple, which couple would you like us to be?
  1. Which moment of ours do you think was the most memorable and romantic for you?
  1. What do you hate most about me?
  1. What do you like best about our relationship?
  1. Have you changed as a person after you started dating me?
  1. Which fictional or real couple would you like us to be?
  1. Are you, friends with your exes?
  1. Is there anything you would like to do for me but haven’t been able to do it yet?
  1. Pick one: cuddling or foreplay.
  1. On a chilly winter night, which romantic movie would you like to watch in bed with me?
  1. What is the sexiest thing you would like to see me wear?
  1. Do you feel jealous when you see me talk to other guys?
  1. What to look for in a romantic relationship?
  1. Rate yourself as a romantic partner.
  1. If I tell you, I am free over the weekend, where would you like to take me?

Dirty Questions To Ask Your Boyfriend

If you plan to turn him on, you can ask him these questions and add a spark to your relationship.

  1. Describe your first-time kiss with me.
  1. Do you fantasize about me when you are alone at night?
  1. What is your favorite position in bed?
  1. What is your sex fantasy?
  1. Do you like kissing me?
  1. Would you like to recreate a sexy scene from a movie with me?
  1. Have you ever kissed in public?
  1. What is the sexiest place that turns you on?
  1. Have you ever felt turned on in a public place?
  1. Do you have a song that always turns you on?
  1. How would you feel if I served you dinner wearing my sexiest clothes?
  1. What is the sexiest object you own?
  1. Pick one: handcuffs or blindfold.
  1. Which character would you like us to play for a sexy role-play session?
  1. What is the dirtiest thought you have had about me?
  1. What turns you on the most?
  1. Which is that sensitive part of you that I can touch to turn you on?
  1. Have you ever been to a strip club?
  1. What is your most preferred time to get intimate?
  1. What is your best feature in bed?
  1. Would you like to kiss me in public?
  1. How long can you make love?
  1. How long can you keep kissing me?
  1. Describe the surprises I can expect from you in bed.
  1. What food would you like to have the next time you are in bed with me?
  1. How do you compliment me when I look sexy?
  1. What’s your master move in bed?
  1. What’s the best way to seduce you?
  1. If you were to get lost on an island with one girl, who would you like it to be?
  1. Where are you most ticklish?
  1. Pick one: jacuzzi or a pool.
  1. Have you ever hooked up with a woman older than you?
  1. Have you ever kissed a boy?
  1. Have you ever wished to see someone naked?

Deep Questions To Ask Your Boyfriend

When in the mood for some serious conversations, you can ask your boyfriend the following questions to help you understand more about your relationship.

  1. Where do you see yourself five years from now?
  1. When was the last time you cried?
  1. What are you most insecure of?
  1. In your childhood, what did you think you would become in the future?
  1. What is your saddest memory?
  1. Do you wish to marry me?
  1. What is the darkest secret you have never shared with anyone else?
  1. What do you think is the strength of our relationship?
  1. Describe our relationship in one word.
  1. What is that you fear most about our relationship?
  1. What is that one mistake in life that you regret the most?
  1. How important is love in your life?
  1. If someone is mean to me, how do you feel about them?
  1. What inspires you the most?
  1. What kind of a life do you wish to live?
  1. What do I mean to you?
  1. What was your most vulnerable moment in our relationship?
  1. What do you think is lacking in our relationship?
  1. Is there anything you would like to ask me but are afraid to do so?
  1. Is there a song that makes you think of us?
  1. Is there anything you want to tell me but haven’t told me yet?
  1. Who do you think works the most toward making our relationship work?
  1. If our relationship ever ended, what do you think would be the reason?
  1. What is your ideal retirement life?
  1. Have you ever told someone you love them but did not mean it?
  1. Is there anything in your life that you are ashamed of?
  1. What is that one moment that changed your life?
  1. What are your unfulfilled dreams?

Fun Questions To Ask Your Boyfriend

If you think your boyfriend is feeling a little low, why not entertain him. You can ask him these fun questions to lighten his mood.

  1. When was the last time you wet your bed?
  1. Have you ever stolen anything from a hotel room?
  1. Did you ever have a crush on your school teacher?
  1. If you received a doll for your birthday, what would you name her?
  1. What animal do you think you could be?
  1. Who was your first celebrity crush?
  1. Where do you hide your stash of dirty magazines?
  1. Have you ever stolen anything and blamed someone else for it?
  1. Do you like your fries with sauce or without sauce?
  1. Pick one: PlayStation, Nintendo, or Xbox.
  1. Who do you think will win in a battle between Superman and Batman?
  1. Are you a cat or a dog person?
  1. Walmart or Target?
  1. Reading a book or watching a movie?
  1. ave you ever cried watching a romantic movie?
  1. Have you ever read a romantic novel?
  1. What is your biggest pet peeve?
  1. What do you notice first in any girl?
  1. Which celebrity would you like to take on a dream date?
  1. How often do you lie?
  1. Have you ever scratched yourself in public?
  1. Do you brush your teeth every day?
  1. Which is your favorite ice cream flavor?
  1. Which was your favorite subject in school?
  1. Have you ever farted in public and acted as if it wasn’t you?
  1. Have you ever peed in a swimming pool?
  1. Name three things you cannot live without.
  1. What is the grossest thing you have ever put in your mouth?
  1. Which is your favorite body part?
  1. Have you ever acted like a girl in front of a mirror?
  1. Have you ever applied makeup to your face?
  1. What is the longest time you have gone without having a bath?
  1. What is the nickname you hate the most?
  1. Is there anything inedible that you would like to eat?
  1. Do you ever have conversations with yourself looking into a mirror?
  1. Which is your favorite ride in an amusement park?

Good Questions To Ask Your Boyfriend

Looking for some topic to talk about with your boyfriend? You can try asking these questions that can help you have a decent conversation.

  1. Describe your most perfect day.
  1. If money was no object, what profession would you choose for yourself?
  1. What is the kindest gesture someone made that moved you a lot?
  1. What makes you feel proud of yourself?
  1. What was the last book you read about?
  1. What trait of yours do you think is most annoying?
  1. What is the one habit of yours that you would like to change?
  1. Did you have a pet growing up?
  1. How were you as a child?
  1. How did you spend most of your summer vacations?
  1. What makes you most nervous?
  1. What is the biggest takeaway from your past relationships?
  1. Which family member were you closest to in your childhood?
  1. What makes you unique as a person?
  1. What is that one mistake you are glad you made?
  1. How do you relieve stress and tension?
  1. As a child, who did you consider your biggest hero?
  1. What is your dream job?
  1. How do you like to spend your weekend?
  1. Which household chore do you hate doing the most?
  1. If given a free trip around the world, which five countries would you visit first?
  1. When was the last time you felt nervous with a woman?
  1. If I come over right now, what would you cook for me?
  1. How do you deal with female attention?
  1. Do you enjoy my company? Why?
  1. Your idea of an ideal proposal?

Important Questions To Ask Your Boyfriend

Here are some personal questions that can help you get a better insight into your boyfriend’s life and understand him better.

  1. Do you have any health problems running in your family?
  1. Is there anything that has contributed to the kind of person you are today?
  1. What is your biggest weakness?
  1. What is your greatest strength?
  1. What makes you angry?
  1. Who do you idolize in life?
  1. How important is money in your life?
  1. What are you most afraid of losing in life?
  1. What do you do when someone hurts you?
  1.  Do you follow a religion or any spiritual teaching?
  1. What is your greatest accomplishment?
  1. Have you ever struggled with any kind of addiction?
  1. Is there someone in your life that you can never forgive?
  1. Have you ever been abusive in a relationship?
  1. Name the person you trust the most in this world.
  1. Have you ever felt like going back to an ex?
  1. What is the one thing you are most attached to in life?
  1. Pick one: love or money.
  1. Have you ever faced any discrimination?
  1. What do you value most in a relationship?
  1. What do you do when you are sad?
  1. What is your life’s biggest dream?
  1. What is your happiest moment in life?
  1. To what extent would you go to help a stranger?
  1. What is the best thing you have learned from your parents?
  1. How do you cope with setbacks in life?
  1. Ever read a book that influenced the way you look at life?

Weird Questions To Ask Your Boyfriend

Every question has a reason behind it. And the few that don’t can be categorized as weird questions. Here are some to ask your boyfriend to break a boring conversation.

  1. What movie scene would you like to experience in real life?
  1. Which is the most important folder on your computer?
  1. What would you advise people to never do in life?
  1. What is the longest time you have gone without sleep?
  1. How would you like your funeral to be?
  1. Can you explain a proverb with a real-life example?
  1. Did you hold any game records in your childhood?
  1. What would you do if you woke up and found out you are the most handsome guy in the world?
  1. Do you still watch cartoons?
  1. What new piece of technology you wish existed in your childhood?
  1. Which is your favorite fashion trend?
  1. Have you ever been caught naked?
  1. If you could wear only one outfit your entire life, what would be your pick?
  1. Do you read your horoscope prediction?
  1. What is your favorite Halloween costume?
  1. Are you a bathroom singer?
  1. If you were a pet, which celebrity’s pet would you like to be? Why?
  1. If one day, you suddenly become superrich, what is the first thing you would buy?
  1. Pick one: reading people’s minds or being invisible.
  1. If you were to be reborn as a girl, who would you like to be?
  1. If you were to be a genius at one skill, what skill would that be? Why?
  1. Who is your favorite animated character?
  1. When you open your window, what would you like to see first?
  1. Which flower do you think is the prettiest?
  1. Have you ever been cheated by an online shopping site?
  1. Would you like to go to a summer camp that you couldn’t go to in your childhood?
  1. If you could talk to animals, which animal would you talk to first? What would you say?
  1. Would you like to sleep with a soft toy?
  1. If you were to die tomorrow, how would you spend your last day on earth?
  1. What is that one thing you own, but you wish you didn’t?
  1. Do you believe in Santa?
  1. Why do you think dinosaurs went extinct?
  1. Would you like to meet an alien?

Do not overwhelm your boyfriend with questions all at once if you want to get to know him. It may exhaust him, and he may not respond as excitedly as you would like. Some of the questions to ask your boyfriend listed above can also be used to start a date night conversation. These questions could contain anything from random inquiries regarding their daily lives to dirty and romantic questions and funny or weird questions. So, shoot some of these questions to understand your boyfriend better.

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