1000 Questions To Ask Your Boyfriend (401 500+ Unique and Interesting Boyfriend Tag Questions — Tag Questions

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Home Love & Romance 150+ Random Questions To Ask A Guy or Girl
  • Love & Romance

150+ Random Questions To Ask A Guy or Girl

Good communication is one major ingredient for a happy and successful relationship. A relationship starts to deteriorate when there is a break in communication. Communication also includes asking questions especially about each other, because the more you understand each other the better the relationship becomes. Despite the fact that you are deeply in love with your boyfriend or girlfriend, there are times when the conversation is dry and you may seem to not have anything to talk about, making the atmosphere boring, this is actually the perfect time to take advantage of and ask him some random but crucial questions. In case you don’t know what to ask, here is a list of some of the random questions to ask a guy or girl.

Random Questions to Ask a Guy or a Girl

What are your regrets in life?

When was the last time you cried?

Describe your relationship with your mother and sister?

Do you sing while taking bath?

Do you snore while sleeping?

Have you ever taken advantage of anyone?

Do you like to clean your room?

If you could live anywhere in the world, where would it be?

Into which personality’s shoes would you like to step for a day?

What 5 words would a close friend use to describe you?

Do you believe in love at first sight?

What is your most treasured possession and why?

What is your favourite month of the year?

Which is the place/country that you want to visit?

What are your hobbies or interest?

Do you like reading? Which is your favourite book?

Do you have a pet name? How did you get it?

Who are all there in your family?

Who is your inspiration?

Which is the best holiday you ever had?

How much do you love me?

Do you dream of a future with me?

Would you accept me if I cheat on you?

Do you approve of working married women?

What is the thing that you like most about me?

Which is your ideal honeymoon destination?

Did you ever have a crush on your teacher or some other woman?

Would you talk to me at night if you are feeling dead sleepy?

Are you a virgin? If not, when did you lose your virginity?

Who do you find most beautiful among my friends?

What was your first impression of me?

Are there any fears you have that you would like to get over?

Do you find yourself prejudiced or biased in any area?

Tell me five of your pet peeves?

If you could have sex with any three people you chose, who would they be?

When you meet someone of the opposite sex, what do you first notice about them?

Which are the parts of their body that you notice?

Have you ever dated two girls at once without either of them being the wiser about it?

Have you ever been arrested or charged with a crime?

Have you ever used being drunk as an excuse for doing or saying something?

Who is your role model?

What do you do in your free time?

Do you like children?

How would you deal with a difficult mother-in-law?

Tell me about your strengths and weaknesses?

What are your career aspirations and dreams?

What’s the hardest thing you’ve ever done?

What is your idea of a perfect Valentine’s Day?

If I ask you to dedicate a song to me, what would it be?

What would you do if I die?

What are the things that you can do to cheer me up?

Do you believe in the seven births companionship concept?

What is your favourite dish?

Who is your favourite actress?

What’s your favourite movie and why?

Would you rather spend a day in the woods or at the beach? Why?

Tell me about a sporting event you’ll never forget

If you could have any superpower, what would it be?

Which is the one job in the world that you would love to do?

If you were an animal in the wild, what would you be?

What is the most embarrassing moment of your life?

Who was your first girlfriend?

Why did you break up with her?

Which is your dream car?

Do you like pets?

Will you like to keep any at home?

If you win a lottery of $1000, what will you do with it?

Are there any causes you strongly believe in?

If you won a million dollars in a lottery, what would you do with it?

If you knew you had only 2 weeks to live and death was imminent what are the regrets you would have?

Why haven’t you done anything about those regrets?

How would you spend those two weeks?

Is there someone from the past you really miss and would like to locate?

Who was your first love?

If you could take a year off and go travelling, where would it be?

Which sports do you play or watch?

Which is your favourite Comic book character?

What do you like about him/her?

If you could relive the last five years of your life, what would you change?

Are you a virgin?

Who did you lose your virginity to?

If a genie granted you 3 wishes, what would you ask for?

If asked to choose between me and your friends, who would you choose?

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

If your life were a movie, who would play you?

If you were a tree, what would be carved in your trunk?

If you had a day off next week and plenty of cash, what would you do?

Would you marry someone much richer or much poorer than you?

How romantic are you?

Do you watch TV serials of women?

Do you go to spas and salons?

Do you ever feel like going away from me?

What is the thing about me that drives you crazy?

Do you smoke and drink?

Have you ever tried drugs?

Tell me about your dirtiest secret?

What are your political leanings?

You have got six months to live, what will you do first?

If you have friends coming over, what would you cook?

Which T.V. program would you never miss?

What is the last CD you bought?

Are you a morning person or a night person?

Where do you see yourself in five years time?

Do you believe a cup is half empty or half full?

Are you an optimist or a pessimist?

If you could travel back through time, what single mistake would you correct in life?

What are the deepest regrets of a person?

Who was your hero, as a child?

If you won a lottery, how would you spend your millions?

What makes you laugh/cry?

Describe your perfect holiday.

Which is your favourite book/movie?

Which is the last book you read?

Which is your favourite music and your favourite singer/band?

Do you like animals/pets?

How do you spend your spare time?

Is there anyone in the world you love so much that you could give your life for them?

If you had the power to just utter a word and kill someone – no one would find out and you would not be charged with a crime, who would you kill and why?

Do you have a role model – someone you want to emulate? Whom do you admire the most?

Do you contribute to any charity? What is the largest amount you have ever given to any charity?

Describe your ideal date.

What type of music do you love listening to?

Tell me about your scariest dream.

What are the five material possessions you will like to save if your house is on fire?

Do you have a pet?

What is the craziest thing that you have ever done?

Do you like to cook?

Have you ever fantasized about your friend’s girlfriend?

Have you ever kissed anyone other than me?

What is the craziest thing you have done?

Have you ever committed a petty crime?

Have I lived up to that impression?

What is that one thing about me that you would like to change?

Are you religious?

Do you pray regularly?

Who is your favourite actor/actress/celebrity and why?

Who is your favourite sportsperson?

What is your favourite sporting activity?

Which is your favourite genre of movies

Which are your favourite shows on television?

Which is the worst date you ever had?

What makes you smile?

What’s your favourite kind of food?

If you could drive any car which one would you choose?

What’s your favourite holiday memory?

If you are given a chance to change something about yourself, what would it be?

Who are you closest to in your family-your mum, dad or siblings?

Do you enjoy your job?

Are you a morning person or a night person?

Tell me about your favourite vacation?

What made it so good?

If you were an animal, what would you be?

If you could try any job for one day – what would you choose?

What do you do to relax?

Are you afraid of darkness?

What is your biggest fear in life?

Which is your favourite sport?

Which is the movie that you never get bored watching?



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  • PairedLife »
  • Relationships

130+ Deep Questions to Ask Your Boyfriend

Updated on June 19, 2017

tutta profile image


I’m Tatiana and am a firm believer in the power of holistic healing and home remedies! Apple cider vinegar for the win!

Contact Author

We are often on the hunt to find things that we have in common with in our partners, which leads to us learning many likes and dislikes by way of asking many questions. One of the qualities that people look for in relationship compatibility is how well they can connect on an intellectual level! Although it’s not important to all, if it is important to one person, it most certainly should be important to the other to ensure great conversation!

One of the ways to test intellectual compatibility is to ask deep questions. To ask your boyfriend deep questions means you are essentially seeing how well he keeps up with important news, to learn his views on controversial topics, and to just see what subjects stimulate him the most. If you are looking for some deep questions to ask your boyfriend, here’s a bunch!

Need questions for your girl instead? Check out 100+ Deep Questions to Ask a Girl !

Video: Deep Questions to Ask Your Boyfriend

Hard Questions to Make Him Think

  1. If you could fix one world problem, what would it be?
  2. If you could live in any era, which would it be and why?
  3. What advice would you give to a person who is just graduating high school?
  4. If you could have chosen your own name, what would you have picked?
  5. If your home was on fire and you only had time to grab 3 things, what would they be?
  6. If you became famous, would you enjoy the limelight or miss your privacy?
  7. If you had $200 to spend on something special just for me, what would you buy?
  8. If you had three wishes, what would they be?
  9. If you were told you have a terminal illness, how would you take the news?
  10. If you only had a week left to live, what are some things you would do?
  11. Would you sacrifice yourself for a stranger?
  12. If a family member needed a kidney and you were the only match, would you give one up?
  13. If I wanted a puppy for my birthday, would you adopt a purebred from a breeder or a mix from a shelter?
  14. You suspect that your neighbors may be abusing their child, do you mind your own business or call the police?
  15. If I went missing, my body never recovered, would you move on or devote your life to looking for me? If you did move on, how long would you wait?
  16. If you could invite 3 people to dinner, who would they be?
  17. If you could live til you were 90 and either have the mind or body of a 30-yr-old, which would you choose and why?
  18. If you could wake up tomorrow and have gained one ability, what would it be and why?
  19. If a crystal ball could tell you the truth about your life, me, or the future, what would you want to know?
  20. If you could live anywhere, where would you live?

Personal Questions to Learn About How He Sees Himself and What He’s Like Inside

  1. Which one fits you better? “Live for the moment”, or “Save the best for last”?
  2. What’s your favorite thing about yourself?
  3. If you could change anything about yourself, what would it be?
  4. Do you prefer going out or staying in?
  5. Would you consider yourself an externally motivated or internally motivated person?
  6. How do you deal with failure?
  7. Do you put more attention to the people around you or the things around you?
  8. When things break, do you prefer to fix them or replace them?
  9. Would you consider yourself materialistic?
  10. What would you consider a perfect day?
  11. What would be your perfect date night?
  12. What are some things that offend you?
  13. What is one thing that you cannot start your day without?
  14. If you’re stressed out, what helps you wind down?
  15. When you die, do you want to be buried or cremated? Why?
  16. What inspires you?
  17. Would you consider yourself an optimist, pessimist, or realist?
  18. We notice an old man living out of a shopping cart behind a grocery store. What is your first thought about him?
  19. Someone calls me something horrible. Do you let me fight my own battles, or jump in and defend me?
  20. Do you think it’s okay to have a close female friend at work?
  21. What are three things you are willing to splurge on for yourself?
  22. What’s something that no one else knows about you?
  23. Do you ever rehearse a phone call beforehand?
  24. When did you last sing to yourself? To someone else?
  25. What are you most thankful for?
  26. Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?
  27. What do you most fear about getting older?

Questions to Know More About His Past

  1. Have you ever done something you regretted?
  2. Where do you see yourself in five years?
  3. What is your happiest memory?
  4. When was the last time you shed a tear?
  5. What is a tradition you did as a child that you want to do with your kids someday?
  6. What are some things in life that you had to learn the hard way?
  7. Do you have any dreams from childhood that you can vividly recall?
  8. What were your childhood aspirations, and how have they changed?
  9. How do you picture your life when you’re 60?
  10. What is your most terrible memory?
  11. How have you changed the most since you were younger?
  12. In what areas do you want to change the most?
  13. When was the first time you were in love?
  14. When was the first time you said I love you?
  15. Is there any book that changed your life?
  16. What is your biggest insecurity?
  17. Is there anything you’re ashamed of?
  18. Is there anything you wouldn’t want your family to know?
  19. If you could change anything about the past, what would it be?

Political Questions

  1. Why do you think the divorce rate is so high nowadays?
  2. What do you think is the biggest flaw of the welfare system?
  3. If you were running for president, what are three key things you would include in your campaign?
  4. Are you pro-choice or pro-life?
  5. How do you feel about genetically modified food?
  6. What is one thing that you feel would make any small business owner more successful?
  7. What invention do you think has done the most for the human race?
  8. Should children be allowed to have cell phones?
  9. Do you think a person’s outward appearance says anything about who they are as a person?
  10. How important do you think it is to do well in school?
  11. Would you consider yourself proud to live in this country?
  12. Is there anything too serious to be joked about?
  13. What are your views on the political system?

Questions to Learn How He Feels About Relationships

  1. What is your position on premarital sex?
  2. What do you look for most in a spouse?
  3. What religious/spiritual views do you have and why?
  4. How important is it for you to save money?
  5. How important is it for you to invest money?
  6. How important do you think sex is in a marriage?
  7. If one of us had to move far away, would you be able to handle a long distance relationship?
  8. What is one thing that can destroy a relationship and never be forgiven?
  9. Do you want to have kids someday when you meet the right person?
  10. Do you think it’s more important to work or spend time with family?
  11. What are three key elements in every successful relationship?
  12. Do you think people can or should be friends with their exes?
  13. Do you believe emotional ‘cheating’ is just as bad as real cheating?
  14. What do you think of open relationships?

Questions to Learn About Your Relationship and How He Feels About You

  1. When did you first realize you wanted to be with me?
  2. Are you looking for commitment?
  3. What was your first impression of me?
  4. Would you surprise me with an expensive gift, or would you consult me before spending the money on it?
  5. Would you rather I be good in the kitchen or good in the bedroom?
  6. What do you think is more admirable, a stay-at-home mom or a career driven mom?
  7. Would you rather leave a big impact on the world or a big impact in your family?
  8. What song do you think best fits our relationship?
  9. What famous real or fictional couple reminds you the most of us?
  10. Do you think a proposal should be a grand public display or a private intimate moment?
  11. If we had children, what features would you want them to get from you and which from me?
  12. What is something you appreciate about me?
  13. What do you think are three things we have in common?
  14. What are the biggest differences between us?
  15. Is there anything in our relationship that you think we need to work on?
  16. What’s something you could never compromise about?

Deep, Serious, and Spiritual Questions

  1. Do you believe in heaven?
  2. Do you believe in soulmates?
  3. Do you forgive and forget or forgive and remember?
  4. If you had kids, what would be your biggest hope and biggest fear for them?
  5. What is one area in your life where you feel like something is missing?
  6. Do you believe there is good in everyone?
  7. Do you think your significant other can be both your best friend and your lover?
  8. Do you think it’s better to have the worst house in a nice neighborhood or the best house in a bad neighborhood?
  9. Is life anything like you had pictured it would be growing up?
  10. Would you rather have a life full of love or a life full of money?
  11. Can a positive outlook make any situation better?
  12. Do you think children are more of a blessing or a burden?
  13. Do you believe in the phrase “opposites attract”?
  14. Who are three people in your life that you would risk dying for?
  15. If I was giving birth to our child and complications arose that meant only one of us would make it, who would you save?
  16. What would you want said about you after you die?
  17. If you could go back in time to give advice to your younger self, what would you say?
  18. What is your life story?
  19. What roles do love and affection play in your life?
  20. Complete this sentence: “I wish I had someone with whom I could share . . . .”
  21. If you died tonight, is there anything you’d regret not having told someone?
  22. Of all the people in your family, whose death would you find most disturbing and why?
  23. What’s a problem you’re dealing with right now?
  24. What’s the biggest struggle that you’ve ever faced?
  25. Would you let me help you with your biggest problems?

Make Things Fun

As much as I love asking my man some serious questions to find out what he’s really thinking, a long list of deep questioning might feel like a bit straining, so I definitely recommend mixing up the serious questions with some fun ones to keep things light and keep the conversation moving!

Once you and your boyfriend are ready to lighten the mood, be sure to check out these lists for more interesting question/answer sessions!

  • 100 Funny Questions to Ask Your Boyfriend
  • 100 Dirty Questions to Ask Your Boyfriend

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    • profile image

      Selina rose 

      4 months ago

      Interesting article

    • Vishwanath11 profile image


      4 months ago

      nice one post

    • profile image

      As a guy, im telling u these questions are a BAD idea 

      5 months ago

      As a guy, im telling u these questions are a BAD idea and only work when the conversation is happening in your head… by your self!

    • profile image


      5 months ago

      How can can i date two boys at the same time cant choose

    • profile image


      6 months ago

      How can I love him !

    • profile image


      7 months ago

      Wow this is so amazing and sometimes you are scared of asking but if you don’t ask you won’t know. In the past I have asked really deep questions but with 2 bottles of wine to take the edge of a bit lol

    • tutta profile imageAUTHOR


      8 months ago from Florida

      Thanks, Heather. I do too. I’m glad you liked my question ideas.

    • profile image


      8 months ago

      Really love is hurt sometimes. Now how can l have a peaceful relationship with my girlfriend, l mean to forgive her & forget ? after l heard a hectic stories years back about her past

    • HeatherMD87 profile image


      8 months ago

      I think this is really important in developing a relationship.

    • profile image


      9 months ago

      Why are these questions more like opinions

    • profile image


      11 months ago

      i dont have boyfriend but this nice article good work



    • profile image


      13 months ago

      Please take me off your Pinterest list–I do not want this in my Pinterest page–I have no need for these–Thank You very much!!!!!

    • profile image

      Sherry cutters 

      15 months ago

      Yes it’s true

    • profile image


      16 months ago

      You ask the best questions

    • profile image


      16 months ago

      Loollll like i would answer any of these to my side hoes cause thats all i got…YOLO

    • profile image


      17 months ago

      i love this it helped me a lot with my relationship.

    • Matty Fernandez profile image


      18 months ago from New Jersey

      Great for self-reflection, first, then ask the boyfriend/girlfriend and see how compatible you are. We should go deeper on the personal questions. Too often we are afraid, but if you marry that person you want to know what you are getting into.

    • profile image

      Ben Bover 

      18 months ago


    • profile image


      19 months ago

      I think some are good questions to ask friends as well!

    • profile image


      19 months ago


    • profile image

      Anonymous Person #432 

      20 months ago

      I get the cutest answers from him when I ask him some of these. "What’s your happiest memory?" "The day I met you."

    • profile image


      20 months ago

      I like helps me a lot thank you!

    • profile image

      great q and a 

      20 months ago

      i like this question it help my relationship thank u

    • profile image


      20 months ago

      My boyfriend shared this with me. I love it! Very conducive to our personal discoveries of each other….

    • profile image


      21 months ago


    • Jane Belle profile image

      Jane Belle 

      22 months ago

      Interesting hub! I would consider asking some of those to my boyfriend 🙂

    • profile image


      23 months ago

      Nice list but i need something a bit more complicated and alot more deeper

    • profile image


      23 months ago


    • profile image

      benny boo 

      2 years ago

      Wonderful list, very interesting

    • profile image


      2 years ago


    • Glenn Stok profile image

      Glenn Stok 

      2 years ago from Long Island, NY

      Many of these questions are useful for a guy to ask a girlfriend too. In addition to asking a potential mate these questions, they are also great to ponder oneself just to get to know ourselves better.

      I actually found it a little difficult to answer some questions in the privacy of my own living room without sharing with anyone else. That just goes to show how much we still can learn about our own feelings about things. I know that wasn’t the intention of your hub, but it’s an additional powerful outcome from your efforts with compiling this list.

    • misterhollywood profile image

      John Hollywood 

      2 years ago from Hollywood, CA

      Interesting and informative question. They certainly made me think a lot. Great hub!

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