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200+ Questions to Ask Your Boyfriend – Over Text or In Person!

Looking for Questions to Ask Your Boyfriend? Good news – you have come to the right place!

Whether you are in a new relationship or you’ve been with your significant other for a long time, communication is essential. For new relationships, communication is how you get to know each other. Keeping up communication will help strengthen the connection between couples who have been together for a while.

Maybe you’re starting a new relationship, or perhaps you and your boyfriend have been together for so long it seems that you don’t have anything to talk about at times. Or, your beau may be a little shy, and you’re having trouble getting him to open up. No matter your relationship situation, these questions are sure to get your man talking.

In this article, you will find over 200 questions to ask your boyfriend. These questions range from deep and thought-provoking to fun and flirty to plain random and silly. Whether your guy is outgoing, shy, or somewhere in between, these questions will help you learn a lot about him and possibly strike up some interesting discussions.

You don’t have to ask him every single question in this article. This is just a broad range of questions to get the conversation flowing. Depending on how long you’ve dated, you may want to start with some of the flirty, fun, or exciting questions and build up to the romantic and deep ones.

Deep Questions to Ask Your Boyfriend

These questions are great if you want to dig deep and really get to know your boyfriend or get him to open up. If your relationship is new, you may not want to ask any of these questions first. Remember to keep an open mind when he answers and let the conversation flow naturally.

What song makes you cry?

What is your favorite childhood memory?

Are you sentimental?

What is one thing you’ve always wanted to do but never got the chance?

What is your biggest insecurity?

What is your biggest fear?

What is your biggest regret?

What is the best advice that you have ever been given?

What is a bad habit that you have had in the past but have overcome?

How often do you change your view of the world?

What three events do you think have had the most significant impact on your life and shaped you into who you are today?

What is the last movie that made you cry?

Have you ever done a random act of kindness? If so, what was it?

What is one small thing that people can do daily that will significantly improve their life?

When you were growing up, who was your role model?

What is one thing that people misunderstand about you?

When was one time that you stepped out of your comfort zone?

What is the most important lesson that you have learned?

How important is religion or spirituality to you?

Can money buy happiness?

What tradition did your family practice when you were growing up that you would like to continue if you have children?

What is one piece of advice you would give your younger self?

If you could fix one problem in the world, what would it be?

If you had to live without one of your senses, which one would you choose to live without and why?

Are you more motivated by praise or criticism?

What is the biggest fear that you have overcome?

Do you believe there is a difference between living life and just existing?

Would you want to be well-known in life but forgotten in death, or unknown in life but remembered forever after death?

What is one thing you would like to accomplish before you die?

Who do you think would come to your funeral?

 What was a nickname you had when you were younger that you hated but your parents loved?

Have you ever had a near-death experience?

Do you believe what goes around comes around?

What is the best way to earn someone’s respect?

Do you follow your heart or your brain when making important decisions?

See more: This or That Questions for Couples

Fun Conversation Starters for Beau

These questions are meant to be precisely what the title implies: fun but not necessity dirty questions. Not only will they give you a glimpse of his sense of humor and what he finds funny, but he will find out what you find funny by the type of questions you ask.

What is the most embarrassing thing you’ve ever done or that has ever happened to you?

What is the most spontaneous thing you’ve ever done?

Who is your favorite comedian?

What is the stupidest thing you have ever done?

What is your go-to karaoke song?

What is the most ridiculous thing you have ever seen?

What is the dumbest trend that is popular right now?

What is the funniest catchphrase you have ever heard?

What is one thing that makes you burst out laughing?

Is there any word that makes you laugh every time you hear it?

What is the funniest movie you’ve ever seen?

What is the weirdest smell you have ever smelled?

What is the best Wi-fi name you have seen?

What is the most ridiculous fact that you know?

What is something that you think everyone looks stupid doing?

What is the funniest joke that you have memorized?

What is the weirdest thing you have seen at someone else’s home?

What is an odd question that you have always wanted to ask me?

What is a movie or TV show that you really like and are embarrassed to tell anyone?

Who can you do a voice impression of?

What is the funniest name you have ever heard?

What is the creepiest thing you could say to a stranger?

Where is the most inappropriate place you have ever passed gas?

What is the best prank you can play on someone?

What is the funniest or most ridiculous tattoo that you have ever seen?

What is the weirdest thing you have seen while you were driving?

What is the most annoying commercial?

What is the funniest or weirdest inside joke you’ve ever been a part of?

Have you ever peed in a pool?

Has anyone ever walked in on you while you were in the bathroom, or have you ever walked in on anyone in the bathroom?

What is the scariest movie you have ever seen?

What is the weirdest conversation that you’ve ever overheard?

Do you have any odd family members?

quizzes for couples

Questions to Ask When You’re Bored

Are there long uncomfortable silences when you and your boyfriend are on the phone? Or maybe you have found that you don’t have much to talk about at dinner.

These questions are great ice breakers and conversation starters. Some of them are random, some are just plain silly, but they all are guaranteed to get the conversation flowing and hopefully get a few laughs out of both of you.

What would you do if you caught me sleepwalking?

Do you prefer the cold or warm side of the pillow?

Would you rather be invisible or have X-ray vision?

If you could be invisible for a day, what would you do?

What superpower do you wish you had?

Is a hotdog a sandwich?

Does pineapple belong on pizza?

What movie do you like to watch over and over?

What is your dream road trip destination?

What would you rename yourself if you could change your name?

Would you rather leave your hometown and not be able to come back, or stay in your hometown but not be able to escape?

Which celebrity would make the worst leader of a country?

If you built a treehouse, what would it look like, and what would be in it?

What could you give a thirty-minute impromptu speech on?

What celebrity would be the worst dinner guest?

What topic do you know WAY too much about?

What is your favorite card or board game?

What is your least favorite card or board game?

What celebrity do you think is a massive jerk in real life?

Do you collect anything?

Who is famous for their talent, but they really shouldn’t be?

How old would you be if you had to be one age forever?

What is your favorite season?

What is your favorite holiday?

If you could learn any language, what language would it be?

Which food do you go for first at Thanksgiving dinner?

What movie title currently describes your life?

What was your favorite class in school?

What was your least favorite class in school?

If you had a time machine, would you go back in time, or would you travel to the future?

Do fish have necks?

Romantic Questions to Ask Your Boyfriend

These questions are ideal for getting to know more about your partner on a more romantic level, without turning the heat up too much. If you don’t know much about your boyfriend’s romantic side yet, these will surely help.

What is your idea of a perfect date?

Do you know your love language?

What is your favorite thing we do together?

Do you think we would have dated in high school?

What is your favorite restaurant that we eat at together?

What is a romantic honeymoon destination?

What do you remember most about the first time we met?

What is your favorite love song?

What would be your perfect romantic date night?

What is your favorite romantic movie?

Which connection is more important in a relationship, an emotional or physical one?

What relationship do you admire from your friends and family the most?

Have you ever kissed someone under the mistletoe?

What is something that you didn’t want me to know about you when we first started dating?

What is your favorite memory of us?

What is your favorite way to show affection?

What is your favorite way to receive affection?

What is one thing about our relationship that makes it unique from other people’s relationships?

If we could take a trip together anywhere right now, where would you want to go?

Which one of us is more affectionate?

What song makes you think about me?

Do you like grand romantic gestures or smaller ones?

What is one difference between us that you love?

What is one similarity between us that you love?

What advice would you give someone about long-distance relationships?

After having a bad day, would you prefer a nice dinner out or a cozy movie night?

What is an item on your bucket list that you would like us to accomplish together?

What is one thing about yourself that you’ve never told me before?

If there was one cookie left, would you give it to me?

Has being in a relationship with me helped you learn more about yourself?

Questions to Ask Over Text

Even if you’re not talking in person or over the phone, you can still ask questions! These are especially good if you haven’t been seeing each other very long, but they work for long-term couples as well. Some of these questions can also be asked in person, but many make more sense when asked via text.

What is your favorite meme or gif?

Does double texting bother you, or is it no big deal?

Do you prefer the beach or the snow?

Would you rather live in another country or outer space?

What’s your favorite place to get carry-out or delivery from?

What app do you use the most?

What is the one app that I might not have that you think I should get?

What is the best picture you have ever taken on your phone?

What is the worst text that you accidentally sent?

What is the funniest picture you have on your phone?

What is the most ridiculous thing you have seen online?

What is your biggest pet peeve on social media?

Are you an early bird or a night owl?

If you were a color, what color what you be?

What food are you craving right now?

What song always puts you in a good mood?

How many phones have you broken or lost?

What is your phone or computer wallpaper?

What is your favorite podcast?

Would you rather be hot or cold?

Which do you prefer: roller coasters or Ferris wheels?

What is your favorite emoji?

What is your favorite ice cream flavor?

Do you believe in aliens?

What is your favorite animal?

If you could be any animal, what would you be?

If you were a dog, what kind of dog would you be?

If you could only listen to one song for the rest of your life, what song would it be?

If you were forced to choose only one food and one drink to have for the rest of your life, what would they be?

Would you rather spend a week in New York City or Los Angeles?

Would you rather have 24 hours of sunlight or 24 hours of moonlight?

What television show could you binge-watch all day?

If you could cancel one television show, what would it be?

Are you an introvert or an extrovert?

If you could, would you quit your job and travel the world?

See also: Get to know you questions

Interesting Questions to Ask

This is a combination of different types of questions. Some are funny, freaky some are random, and some are thought-provoking. But they are all interesting, and not only will they tell you more about him, but they will also show him how interesting you are as well!

Most of these are open-ended, and the answers require some explanation, so ask away and get ready for the conversation to take off.

What is your biggest pet peeve?

If you could have dinner with any famous person, living or dead, who would it be?

What is the weirdest thing that you have in your closet?

What activity or thing calms you the most?

What seemed normal in your family growing up but seems weird now?

If animals could talk, which animal would be the rudest?

If you could be a part of any TV family, which family would it be?

Who would you pick to play you in a movie?

What is your ideal weekend?

What was your favorite TV show when you were a child or teenager?

What would you take if you could only take five movies to a deserted island?

What is the worst job you have ever had?

What is the worst date you have ever been on?

Did you ever go to summer camp?

If you were accidentally put in an insane asylum, how would you convince them that you weren’t actually crazy?

What fictional character is excellent in the book, movie, or television show they’re in but would be impossible to deal with in real life?

What is the most exciting piece of trivia or useless fact that you know?

What historical figure do you think is not as impressive as most people think they were?

What is the worst purchase that you have ever made?

What would be on your perfect burger?

Who is your favorite villain?

What is one thing you like to do that is traditionally considered feminine?

What is something peculiar that you used to eat when you were a child?

Aside from people and animals, what is one thing you would grab out of your house if it were on fire?

What is a weird flavor combination that you like?

What is a random compliment you have received that you have never forgotten?

Have you ever had a paranormal experience?

What movie would be better if the plot were reversed?

What was fun to do one time, but you don’t think that you’ll ever do again?

What is the worst injury you have ever gotten?

If you go to a restaurant and the service is terrible, is it okay not to leave a tip?

If you could prevent one historic disaster, which one would it be?

What is your worst travel trait?

What would be inscribed on your tombstone?

How do you avoid procrastination?

Flirty Questions to Ask Your Boyfriend

If you’re feeling flirty or want to ask him some fun cute questions without getting too deep or romantic, these questions are perfect. Plus, some of these questions may be excellent icebreaker questions to lead up to the more romantic ones.

What is the best pickup line you’ve ever heard?

What is the worst pickup line you’ve ever heard?

How old were you when you had your first kiss?

Do you check out your reflection?

Who is your celebrity crush?

What was your first impression of me?

What couples costume have you always wanted to do for Halloween?

Do you smile when you receive a text message from me?

Would you rather hug for five seconds or kiss for one second?

What is the craziest thing you have ever done to impress someone?

Which do you like better: movie dates or restaurant dates?

Do you enjoy staying in or going out?

Do you think that men should always make the first move, or is it okay for women to make the first move?

Have you ever randomly kissed someone in the middle of a conversation?

What did you think when you first saw or met me?

Are you ticklish?

Would you rather be married to a 10 with a horrible personality or a 6 with a fantastic personality?

Do you ever still get nervous around me?

What do you think is your most attractive non-physical feature?

What is my most attractive non-physical feature?

Would you rather be called sexy or intelligent?

Would you rather never be able to kiss or never be able to cuddle?

Would you ever write a song or a poem for me?

Do you like pet names, or do you think they’re silly?

Are you a good dancer?

Would you ever lay on the grass and watch the stars with me?


I hope this list of more than 200 questions will be helpful the next time you’re bored, feeling flirty, or feel like you’ve run out of things to talk about with your boyfriend. Good luck!