200 + Best Deep Questions To Ask Your Boyfriend & Crush

We are usually on the hunt to search out things that we have in common with our partners, which leads to us learning several likes and dislikes by the approach of asking deep questions to ask your boyfriend. One of the qualities that people search for in relationship compatibility is how well they can connect on an intellectual level! although it’s not necessary to all, if it is necessary to one person, it most definitely should be necessary to the other to make sure nice conversation!

There are many ways but one of the way to check intellectual compatibility is to ask deep questions. To ask your boyfriend deep questions means that you are basically seeing how well he keeps up with the necessary news. To find out his views on controversial topics, and to simply see what subjects stimulate him the most. If you are trying to find some deep questions to ask your boyfriend. Here is a wide range of these type of questions!

Remember, these deep questions to ask a guy are for exploring deeply into topics like human nature. The future of the humanity, and ethics. Thus ensure to ask to follow up questions and let the conversation go wherever it needs to go.

Deep Questions To Ask Your Boyfriend

Deep Questions To Ask Your Boyfriend

If you are searching for the most effective questions to ask your boyfriend to understand him better and to make a deeper connection between you two. Then you have landed on the correct place. This list of questions relies on the actual fact that you simply two are already dating for some time.

Romantic Questions To Ask Your Boyfriend

  • Do I make you want a future with me?

  • What do you love about me the most?

  • Would you risk your life to save mine?

  • Do you believe in love at first sight?

  • Would you sacrifice something to keep our relationship going?

  • Do you remember the day we met?

  • Do you feel like you can tell me anything?

  • If you have a vision of the perfect date to take me on, what is it like?

  • Do you believe in soulmates?

  • Would you be my lover in the next life?

  • What was your first impression of me when we actually met?

  • Is there a song that you think of when you think of me?

  • What was the first thing that you noticed about me that made you feel attracted?

  • What are the qualities you like in me the most?

  • How special is a memory of your first love to you?

  • When did you have your first crush?

  • What is the craziest thing you can do for me?

  • What roles do love and affection play in your life?

  • Who are three people in your life that you would risk dying for?

  • Do you think your significant other can be both your best friend and your lover?

  • Would you introduce me to your parents?

  • What is a quirky thing about me that you love?

  • How would you describe our first kiss?

  • If I was scared, would you hold me?

  • Do you like kissing in the dark or kissing in the rain more?

  • When you’re alone, do you think about me?

  • Would you hold my hand in public?

  • What is your favorite dream that involved me?

  • Would you kiss me in public?

  • Does it make you smile when I send you a text message?

Questions To Show Interest In Your Boyfriend

  • Can you repair your own car?

  • Describe your dream house.

  • Do you like to travel?

  • Describe yourself in a single word.

  • If you could only eat one food the rest of your life, what would it be?

  • Are you close to your parents?

  • What’s your dream job?

  • Who is your favorite superhero? What would you do with his or her super-power?

  • What is your favorite rainy day movie?

  • If you’re having a bad day, how can I cheer you up?

  • What makes you smile?

  • What is that one place in the world you would like to visit at least once in your life, and why?

  • What’s your favorite sport to play or watch?

  • Have you cried at any movie?

  • What are your hobbies?

  • Do you think of yourself as being nice or naughty?

  • What is your most favorite meal?

  • Are you a morning person or night owl?

  • What’s your most favorite music genre?

  • What is your most favorite romantic activity?

  • Are you religious or spiritual?

  • What was the last book that you got so absorbed in that you couldn’t put it down?

  • What´s the best vacation you´ve ever had?

  • Are you a superstitious type of person? About what?

  • What three events made the biggest impact on who you are today?

  • How many phones have you broken or lost?

  • What´s your relationship like with your mother?

  • Do you prefer going out or staying in?

  • How many days a week do you get together with friends?

  • Is there anything you wouldn’t want your family to know?

Deep Though-Provoking Questions

  • What would you change about your life if you knew you would never die?

  • Does truth exist without evidence? Without proof of something, can it really be considered a truth?

  • What is the honor, and does it even matter anymore?

  • If you had a year left to live, what would you achieve over the next 12 months?

  • If you could send a message to the entire world, what would you say in 30 seconds?

  • How many people do you truly love? What are you doing for them?

  • Standing at the gates of heaven, and God asks you “Why should I let you in?” What do you reply?

  • What have you done to pursue your dreams lately? How about today?

  • How do you apply the learning from your past mistakes to your actions today?

  • Is being open-minded a virtue, if it’s causing destructive ideas to spread throughout society?

  • When things break, do you prefer to fix them or replace them?

  • What would you want to be said about you after you die?

  • Do you believe it is good for everyone?

  • Do you forgive and forget or forgive and remember?

  • If you were told you have a terminal illness, how would you take the news?

  • Do you think there is an afterlife?

  • If a crystal ball could tell you the truth about your life, me, or the future, what would you want to know?

  • What is one area in your life where you feel like something is missing?

  • Would you sacrifice yourself for a stranger?

  • What part about the future scares you?

  • If you died tonight, is there anything you’d regret not having told someone?

  • Is life anything like you had pictured it would be growing up?

  • What’s one thing you think makes our relationship unique from everyone else’s?

Sexy Questions To Ask Your Boyfriend

  • Do you like it when I take control in bed or do you like being in control?

  • Of all the things I’ve done with you in the bedroom, what’s your favorite?

  • What is your favorite part of my body?

  • Have you ever had sex in a public place?

  • Try to guess – what’s the color of my underwear right now?

  • When was the last time I was in one of your dreams?

  • Do you sleep in pajamas, underwear or nothing at all?

  • Have you read 50 Shades Of Grey? If so, did it turn you on?

  • What is your biggest turn on?

  • Do you like it when I’m the dominant one in bed or do you prefer leading things?

  • What’s the one thing I do that turns you on the most?

  • How often do you think couples should make love?

  • Have you ever taken naked pictures of yourself?

  • How do you feel about pornography?

  • How often do guys really think about doing it?

  • Is laughing in the bedroom okay with you or do you prefer keeping things serious?

  • You decide to give me a full body massage, where do you start?

  • What was your first “adult” experience?

  • Do you own any sex toys?

  • Have you ever had a one night stand?

  • How can we make our sex life better?

  • What do you think of open relationships?

  • Have you ever done it in a movie theater?

  • Do you like experimenting with different positions?

  • What do you think about dirty talk over the phone or Facetime?

  • Do you like it with the lights on or off?

  • What attempts did you make to woo me? Which ones worked?

  • Where is the most public place that you’ve touched yourself?

  • Has anyone accidentally seen you naked?

Questions To Make Your Boyfriend Closer To You

  • Is there anything you’ve done in the past that you can’t forgive yourself for?

  • Do you still have feelings for someone in your past?

  • Did you ever feel totally insecure about something?

  • Have you ever cheated on a girlfriend?

  • What is your biggest regret in life?

  • What’s the most embarrassing moment of your life so far?

  • What was the first thing you thought of me when you saw me?

  • If you had to choose between all the money in the world or a devoted, loving family, what would you choose?

  • What are you most afraid of?

  • When was the last time you cried?

  • Have you ever been in love?

  • What´s the most disappointed you´ve ever been?

  • Do you have a secret hunch about how you will die?

  • Have you ever had your heart broken?

  • What was your best relationship?

  • What is your worst trait?

  • Have I done anything to hurt you that you never told me about?

  • Were you ever bullied in school?

  • What´s the worst dream you´ve ever had?

  • Do you believe in marriage?

  • What movie do you wish life was more like?

  • Is there anything you’ve done in the past that you can’t forgive yourself for?

  • What do you consider to be your greatest accomplishment in life?

  • What’s your biggest fantasy?

  • Which is better to listen to – your heart or your brain?

  • Would you rather be a good guy or a bad guy in a comic/movie?

  • What childish thing do you still enjoy?

  • Who or what is your nemesis?

  • What was your best drop the mic moment?

  • What long shot have you taken that really paid off?

Funny Questions To Make Him Laugh

  • What career did you want to have when you were in kindergarten?

  • Is there anything you wouldn’t do for 10 million dollars?

  • What was your worst vacation ever?

  • What was the toy from your childhood really creepy?

  • If you made up an ice cream flavor, what would be in it?

  • What is the craziest thing you have done?

  • What nickname would you give me based off my personality or a body part?

  • Will you tell me if I have lipstick on my teeth or if my hair is standing straight up?

  • What is your favorite board game?

  • What’s the weirdest thing you’ve ever eaten and liked?

  • If we were in a group at a party, and I told a horrible joke that no one else laughed at, what would you do?

  • When your dog farts, do you leave the room or tough it out?

  • Have you ever look in the mirror and wink at yourself?

  • What’s grosser: Yellow teeth or yellow toenails/fingernails?

  • Has anyone ever walked in on you sitting on the toilet?

  • If you had to kiss a guy other than family, who would it be?

  • Have you ever peed in a pool?

  • What would be your weapon of choice in a zombie apocalypse?

  • What’s the grossest thing you’ve ever eaten?

  • Would you rather crank call or ding-dong-ditch your neighbor?

  • Do you know how to spell antidisestablishmentarianism?

  • If you had a pet unicorn, what would you name it?

  • Has anyone ever walked in on you in the bathroom?

  • Who was your celebrity crush as a teen?

  • Finish this statement: “Look out! It’s a _____!”

  • What’s the worst movie you’ve ever paid to see?

  • When you were a kid, what did you think being this age would be like?

Ask Questions About Moving In Together

  • Have you ever thought about moving in together? Do you want to in the future?

  • Do you plan to adopt or purchase a pet in the near future?

  • Would you ever consider having additional roommates to cut costs if we had a place with enough space?

  • Imagine we live together. Who will be paying for bills?

  • How will you help me keep the apartment clean?

  • What is your favorite thing to wear to bed?

  • When do you think is the best time for us to move together?

  • How often would you like to have company over?

  • What is your favorite thing to wear when you are at home?

  • If we will live together and suddenly break up, who will move out?

  • How do you like to fall asleep when I’m not there? Do you have any sleeping quirks?

  • How is your actual financial situation? Do you have any debt?

  • What will happen if our sex life slows down?

  • How will we make sure the chores around the house are divided fairly?

  • How will we make room for alone time?

  • Do you see us getting married in the near future?

  • How long do you think we will live together before getting married?

  • What is our ultimate goal of living together?

  • Can you pay your full half of the bills on time every month?

  • How will we usually handle meals?

Questions About His Past

  • When was your first kiss?

  • What’s the worst thing you’ve ever done?

  • What time in your past would you love to return to? Why?

  • What was your parents’ relationship like?

  • How many sexual partners have you had?

  • What are some of your favorite childhood memories?

  • Have you ever broken the law?

  • How did your last relationship end?

  • What do you consider to be your greatest accomplishment in life so far?

  • If you could change anything about the way you were raised, what would it be?

  • What were you like as a child?

  • What is the craziest/weirdest thing you have ever done?

  • How have you changed the most since you were younger?

  • What is your most terrible memory?

  • When was the first time you said I love you?

  • Do you have any dreams from childhood that you can vividly recall?

  • What are some things in life that you had to learn the hard way?

  • What were your childhood aspirations, and how have they changed?

  • Have you ever had a wet dream?

  • What is the most courageous thing you have ever done in your life?

  • Have you ever experimented with legal/illegal drugs?

  • What’s the biggest lie you ever told—did you get busted?

  • Do you still have feelings for someone from your past?

  • How did your last relationship work out?

  • When did you lose your virginity? How did it happen?

  • What’s the riskiest thing you’ve done in life? Sexually?

Future Questions To Ask Your Boyfriend

  • Where do you see our relationship in 5 years?

  • What would you like your greatest accomplishment to be?

  • What are your thoughts on marriage?

  • How important are children to you?

  • What do you want to have going on in your life in 5 years, or 10, or 15?

  • If money were no object, where would you want to live?

  • What is your idea of a perfect honeymoon spot?

  • How many kids do you want to have in the future?

  • What Fictional world would you like to live in?

  • Do you see us getting married in the future?

  • What would you do if I got pregnant?

  • Where is our relationship going?

  • What are some of your goals in life?

  • What do you think of being forever together?

  • When you die, do you want to be buried or cremated? Why?

  • Are you looking for a serious commitment in near future?

  • Do you see me in your future?

  • Would you ever consider moving in together?

  • What do you most fear about getting older?

  • What serious goal do you want to accomplish in your lifetime the most?

  • How will we spend our holidays?

  • What fun goal do you feel you must do before you die?

  • What are your thoughts on how to discipline children?

  • When you die, what part of your personality do you want to be remembered for?

  • What will be the world like in 25 years?

  • Would you ever consider moving in together?

  • What are your retirement plans?

  • What crazy activities do you dream of trying someday?

  • If we were married and my career forced me to move, would you come with me?

Personal Questions To Ask Your Boyfriend

  • What are your retirement plans?

  • How important is a religion? How will we celebrate religious holidays, if at all?

  • Do you have any bad spending habits? How about financial debts?

  • Where do you want to live in the long term?

  • Have you fully disclosed to me your health history, both physical and mental?

  • Do you want to have kids? If so, then how many?

  • Will you support my decision if I want to go back to school one day?

  • What are your thoughts on how to raise and discipline children?

  • How will we handle our in-laws?

  • What do you think each person’s role is in a marriage?

  • How will we spend our holidays when we will have children?

  • Do you want a small wedding, a large one, a visit to the courthouse, an elopement, or do you have no opinion at all?

  • What kind of dad do you want to be?

  • How far should we take flirting with other people? Is watching pornography O.K.?

  • What is your stance on divorce?

  • If I got really sick with a long-term illness, would you stick around to take care of me?

  • How do you see us 10 years from now?

  • What do you think is the best way to handle disagreements in a marriage?

  • Are you a spender or a saver?

  • What does my family do that annoys you?

  • Would you be agreeable to staying home with the kids if my career was about to take off or if I made enough at my job to support that arrangement?

  • If I have a disagreement with one of your family members or friends, will you stand up for me?

Naughty Questions To Ask Your Boyfriend
  • How would you describe your package?

  • Ever try using a sex toy during sex?

  • I drip hot wax onto your chest unexpectedly, how do you react?

  • Do you think you could get me off just by kissing me and touching my breasts? Want to try?

  • Where is the strangest place you’ve ever had sex?

  • Are you quiet, or do you like to make a lot of noise?

  • Do you like your hair pulled?

  • So imagine you can only have one type of sex for the rest of your life – oral, anal, or regular. Which one do you pick?

  • Have you ever had sex with one girl and then had sex with another on the same day? Did they know about each other?

  • Do you prefer having some fun in the morning or at night?

  • Have you ever had a one night stand?

  • What is your favorite thing I do to you in bed?

  • Do you prefer top or bottom?

  • Have you ever been caught going solo? By who?

  • Do you like when I send you dirty pictures?

  • Under the sheets, are you Iron Man, The Hulk, Thor, or Captain America?

  • How many rounds do you think you could go in one night? What about on our wedding night?

  • Do you like playing rough?

  • What’s the longest you’ve gone without doing it?

  • Do you like it when I go down on you?

  • If I could only wear yoga pants or short skirts for the rest of my life, what would you choose for me?

  • Do you like watching me touch myself?

  • What’s your favorite thing to do to me?

  • Have you ever woken up beside someone you regretted sleeping with?

  • Do you want to know what I’m wearing?

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