286 Questions to Ask Your Boyfriend (For Any Situation)

How well do you know your boyfriend? Like, really know him? It doesn’t matter if you have been dating for a few months or a few years; there is always more to learn about the person you’re with.

Whether you are in the beginning stages of your connection and are in need of inspired conversation starters to help you get to know each other better, or have been dating for quite some time and are looking for the right questions to ask to deepen your relationship with your significant other, you have come to the right place.

The questions in this article are great to ask either over text to keep a conversation interesting or as conversation topics to cover on your next date night.

Sections

  1. Important and serious questions
  2. Romantic
  3. Fun
  4. Deep
  5. Cute
  6. Flirty
  7. Intimate
  8. About you
  9. About him
  10. Hard
  11. Weird
  12. Random
  13. Truth or dare
  14. Common questions and important considerations

Important and serious questions to ask your boyfriend

When you are hoping to take any relationship to a deeper level there are certain questions that are important to ask. Here are 50 questions that will help you to gain clarity around your relationship.

Relationship compatibility

When you start dating someone new, it can be easy to get lost in chemistry and physical attraction. While both of these things are important parts of being with someone romantically, they are not the only things that matter. It might feel scary bringing topics up like this with a new boyfriend, but don’t be so afraid of asking the wrong question that you end up wasting time with someone who isn’t compatible.

1. Are you a night owl or early bird?
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2. Do you like moving around or prefer to be settled in one place?
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3. Are you adventurous or more of a homebody?

4. How do you envision your perfect day?
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5. Do you see yourself wanting kids one day?
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6. How important to you is self-development?

7. How do you deal with stress in your life?
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8. How do you express love in a relationship?
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9. Would you consider yourself to be a workable partner?

10. How do you envision splitting finances with your partner?

Questions to ask your boyfriend about your relationship

It’s never a bad idea to check in with your partner to see how both of you are feeling about your relationship and figure out if there are any areas that need extra attention. By creating an open and ongoing conversation about the ways that you can connect and support each other more deeply, you are much more likely to have a relationship that lasts. Help build deep intimacy with the following questions.

1. When we fight, do you feel like we resolve the issue?
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2. Are there any ways I could make you feel more loved?
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3. What is your favorite part of being with me?

4. Can you see us being together long-term?
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5. Do you feel supported by me in our connection?
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6. Do you feel safe bringing up serious issues with me?

7. Is there anything you feel is lacking in our relationship?
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8. What’s your happiest memory with me?
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9. Do you feel respected by me?

10. When do you feel the closest to me?

Serious questions to ask your boyfriend about the future

Being aware of the dream that you have for the future and the way that your partner fits into it is an important piece in being able to make it a reality. Spend some time getting clear on your vision, and then share your goals for the future with your partner. By doing so, you two have the opportunity to collaborate on making it a reality.

1. If we bought a house, where would you want it to be?
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2. What is a goal of yours for our relationship?
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3. Are there any aspects of our relationship that you don’t think are sustainable long-term?

4. Do you see yourself wanting to have kids with me?
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5. What are your financial priorities?
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6. Where do you see us in 5 years?

7. Can you see yourself being in the same career long-term?
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8. When you picture yourself at 50, what do you see?
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9. How important is having a family to you?

10. Is there anything on your bucket list that we could do together this year?

Questions to ask your boyfriend before moving in together

Moving in with your boyfriend is a big decision and one that should not be made lightly or for the wrong reasons. Regardless of how much you love your partner, there are issues every couple faces when trying to organize everyday life with someone new. Take time to understand what you and your partner need to make home life work for both of you before making the big move. Find out if you’ll make good housemates with the following 10 questions.

1. On a scale from 1-10, how clean do you want your house to be?
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2. How do you envision sharing household responsibilities
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3. How much alone time do you need?

4. Do you like entertaining guests or prefer to have the house to yourself?
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5. What is our intention for moving in together?
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6. How do you envision us spending a day together?

7. How would you like to split household expenses
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8. When we’re fighting, do you need time to process or want to resolve it immediately?
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9. How much physical space do you need for yourself in the house?

10. Do you prefer cooking at home or eating out?

Questions to ask your boyfriend before getting engaged

If you are considering getting married to someone, then it’s important to not be too shy to ask important compatibility questions before doing so. You need to make sure that you are with someone who you can have uncomfortable conversations with. An important part of healthy relationships is open communication. Don’t avoid difficult conversations. Get to know your potential husband better by asking the following questions before marriage.

1. Who are your relationship role models?
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2. If we do have kids, how do you envision splitting the parenting responsibilities?
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3. Would you feel comfortable supporting your partner to be a stay-at-home mom?

4. How do you feel about the idea of being with only one person sexually for the rest of your life?
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5. How important is buying nice things to you?
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6. What are your priorities in life? Can you ever see them changing?

7. Is my debt your debt?
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8. How did your family deal with conflicts? Is that how you still deal with conflicts?
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9. How important to you is open communication?

10. Do you picture us doing everything together or still having autonomy?

Romantic questions to ask your boyfriend

In long-term relationships, the “feel-good” chemicals wear off after a while, and it might feel like the romance is fading.[1] This can be attributed to why a lot of couples feel as though their relationship loses its spark over time. If you are dedicated to keeping romance alive with your partner, here are some great questions to ask while texting and in person during your next date night.

1. Do you know how handsome I think you are?
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2. When do you feel the sexiest?
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3. Do you still get butterflies when I call or text you?

4. Can you see us growing old together?
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5. What’s your favorite pet name that I’ve given you?
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6. When we’re apart, what do you think about me the most?

7. What is your love language?
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8. What is your dream vacation with me?
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9. What do you think is your superpower?

10. What is a romantic fantasy of yours?
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11. How would you spend the perfect night with me?
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12. When do you feel the most loved by me?

13. What do you think is my favorite part of you?
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14. What is a relationship dream you have with me?
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15. How much do you love making love to me?

16. How adorable would our babies be?
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17. What’s your favorite time of the day to be intimate with me?
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18. What is your favorite memory of us together?

19. What’s your favorite thing about being intimate with me?
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20. Do you think love at first sight is real? Is that how you felt with me?
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21. Where is your favorite place to be with me?

22. What song makes you think about me?
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22. If our relationship ended, what would you miss the most about me?

Fun questions to ask your boyfriend

If you are looking for some good and fun questions to ask your boyfriend to make him laugh, these are the perfect choice for you. Not everything always has to be serious, and sometimes simply sharing a laugh with him is exactly the kind of connection your relationship needs.

1. What is one toy you always wanted as a kid?
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2. What is the most “unmanly” thing you do?
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3. What game or reality show do you think you would do really well on?

4. Be honest, do you prefer being the big or little spoon?
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5. What did you want to be when you grew up?
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6. Do you think you could be with me if I was 1ft taller than you?

7. How seriously do you take horoscopes?
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8. What fictional place would you visit if you could?
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9. If you could choose any language to immediately be fluent in, what would you choose?

10. What book or movie are you embarrassed to admit you like?
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11. If you had to marry one of your best guy friends, who would you choose?
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12. Would you rather be able to eat anything you want and never gain weight or be able to read people’s minds?

13. Would you ever come for a mani-pedi with me?
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14. Would you get a tattoo on your butt for $1000?
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15. Would you rather meet an alien or a ghost?

16. What is a random job that you think you would be really good at?
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17. How long do you think you would last alone on a desert island?

Deep questions to ask your boyfriend

An easy way to strengthen the bond you have with your boyfriend is by asking deep questions about them and listening closely to the answers. By asking the right questions, you will be able to learn intimate details about his past, and often this gives beautiful insights into how their past continues to shape their present reality. Get to know your boyfriend better with these deep questions.

1. What’s one thing you’re glad you’ll never have to do again?
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2. Do you think that any two people can be in a healthy relationship as long as they communicate well?
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3. Do you feel like your parents did a good job of raising you?

4. What do you consider to be the hardest day of your life?
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5. Do you have any regrets?
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6. Do you feel free in your life?

7. Are you happy overall with your life as it is right now?
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8. What aspect of your life do you find the most fulfilling?
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9. Do you have any dreams that you’re afraid to pursue?

10. What’s the best piece of advice anyone has ever given you?
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11. What has been the biggest blessing in disguise in your life?
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12. Did COVID change your life for the better in any way?

13. What is one time that you wished you could slow down time?
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14. If you could write a note to your younger self, what would it say?
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15. Have you ever struggled with mental illness?

16. What is one quality about yourself you wish you could change?
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17. What do you consider to be your most unloveable quality?
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18. Do you ever struggle with jealousy in our relationship?

19. Where would you live if money and work weren’t a factor?

Cute questions to ask your boyfriend

If you are bored and want to put in some work to keep your man wrapped around your finger, then try adding a few of the following questions into your next conversation with him. They are great to be used in person but will also hit home if you use them over text as well. Enjoy embracing your cuteness with the following questions.

1. If I was a flower, what do you think I would be?
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2. What is the biggest feeling you experience while we are together?
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3. Do you still smile when you see you have a text from me?

4. What reminds you of me?
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5. How would you describe how I smell?
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6. Do you ever think about me during the day?

7. When do you feel the most connected to me?
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8. How adorable do you think our kids would be?
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9. What would you want to name our son?

10. What animal do you think I’m the most similar to?
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11. Do you think I could ever be too in love with you?
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12. What do you see when you imagine our future together?

13. What’s your favorite pet name to call me?
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14. If I’m feeling sad, what do you know will cheer me up?
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15. What is one quirky quality of mine that you love?

16. Do you still love holding my hand?
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17. If you wrote a song about me, what would you call it?
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18. What is the sweetest thing you think I’ve ever done for you?

19. How would you feel if I bought you flowers?

Flirty questions to ask your boyfriend

If you’re the kind of person that feels nervous being flirtatious or suggestive, then using these questions as a way to break the ice might be a great start for you. Let your boyfriend see a more fun and confident part of your personality by asking the following flirtatious questions next time you see him.

1. What do you think I’m wearing right now?
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2. Would you rather see me naked or in lingerie?
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3. Do you know how badly I want you right now?

4. What’s one thing you want to do with me that you’ve never done before?
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5. How did you feel when we had our first kiss?
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6. What do you think is my favorite part of your body?

7. What’s the sexiest dream you’ve ever had about the two of us?
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8. How many times did you want to kiss me before our first kiss?
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9. What’s your favorite part of my body?

10. Would you ever go skinny dipping with me?
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11. Would you ever take a bath with me?
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12. Would you rather see me in a cute dress or a revealing workout set?

13. How do you feel when you stare into my eyes?
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14. Would you eat food off of my body?
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15. What would be your favorite way for me to wake you up?

Intimate questions to ask your boyfriend

At a certain point in your relationship, you need to let go of your fear of asking more personal questions and start creating a more intimate relationship with your partner. Although it might feel scary, the truth is that asking intimate questions to the right person will not scare them away and will instead only work to strengthen the connection between the two of you.

1. Who was your role model growing up?
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2. When was the last time you cried?
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3. Do you feel comfortable crying in front of me?

4. How important is physical attraction for you in pursuing a woman?
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5. What were you most afraid of as a kid?
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6. What’s your biggest fear as an adult?

7. Do you consider yourself to be more of an introvert or extrovert?
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8. If you could choose one big decision from your past to change, what would it be?
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9. Are there any things that you do to show me love that you think I don’t notice or appreciate?

10. Do you feel safe in our relationship?
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11. What do you feel is your biggest talent in life?
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12. What is a dream of yours that you aren’t pursuing right now?

13. When in your life have you felt the most heartbroken?
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14. How free do you feel in your life?
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15. What is your definition of freedom?

16. Is there anything that I make you feel insecure about?
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17. What is something I could do right now to improve your life?
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18. Do you view yourself as more of a nurturer or a protector?

19. Do you think that you have changed a lot this past year?
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20. What are three words you would use to describe yourself?
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21. What is an insult someone said to you that still affects you to this day?

22. Do you consider yourself to be a workable person?
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23. What weird quirks does your body have?

Questions to ask your boyfriend about you

Have you ever thought to yourself, “I wonder what my boyfriend really thinks about me?” Now is the perfect opportunity for you to find out. Don’t be afraid to ask questions about yourself. His answers will be a great insight into how he feels about you, and hopefully they will leave you feeling deeply loved and understood by your partner.

1. Do you think that I make you a better person?
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2. What is your favorite feature of mine?
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3. What would be the best thing about growing old with me?

4. Is there anything I have helped you learn about yourself?
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5. When you’re sick, do you think that I take good care of you?
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6. What do you think is my greatest strength?

7. What is something that I could benefit from working on?
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8. When did you know you were in love with me?
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9. Do I make you feel respected?

10. When do you think I look the sexiest?
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11. What was your first impression of me?
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12. How would you describe me to a friend?

13. If we had kids, what features of mine would you want them to have?
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14. Is there anything you’ve always wanted to ask me but haven’t?
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15. What about me made you want to be with me?

16. What do you think would be a perfect job for me?
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17. What is a quality of mine that you most admire?
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18. Do you think I would be a good mother?

19. What do I do that makes you feel the most loved?
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20. What trait of mine first drew you towards me?
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21. Do you ever dream about me?

22. Do you like kissing or hugging me more?

Questions about him

These are good questions that have been specifically created for you to use to get to know more about your boyfriend in specific intimate areas of his life.

His past

A person’s past plays a big role in who they are, and you can learn a lot about your partner by understanding the challenges, triumphs, and any embarrassing moments that have shaped who he is as a person. Have you always wondered about the experiences that make your boyfriend the man you know and love? Use these questions to get to know more about his past.

1. What has been the saddest day of your life?
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2. What is an experience from your childhood that you feel still deeply impacts you to this day?
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3. What was school like for you growing up?

4. Did you have any pets growing up?
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5. What is something that has always made you happy?
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6. Is there anything about your life that you would want to change?

7. What is the hardest thing you’ve had to do alone?
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8. What is a challenge that you overcame and taught you important life lessons?
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9. What in your life do you feel the most proud of?

10. Why did you and your last ex break up?

His life and family

Many studies have found links between parental behavior during a person’s childhood and their behavior as an adult.[2] If you want to gain a deeper understanding of the habits and perspective of your partner, learning more about his relationship with his parents and family as a whole is a great way to do so. The following questions will give you meaningful insight into the role that your boyfriend’s family plays in his life.

1. Do you feel like you were nurtured enough by your parents?
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2. What’s your favorite childhood memory with your family?
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3. Do you ever wish your parents did a better job of raising you?

4. What’s the best advice that your parents have ever given you?
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5. What is your favorite thing about your mom?
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6. Do you see your parents more as parents or friends?

7. Who in your family would you go to if you needed support?
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8. Do you have a large extended family? Are you close with them?
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9. Did your parents set a good example of healthy relationships for you growing up?

His worldview and values

How your partner sees the world will definitely play a role in how easy it is for the two of you to have long-term longevity. Although you can have a connection that is largely based on chemistry or physical attraction with just about anyone, being with someone who shares the same opinions and values with you will make life with them that much easier. These are great questions to ask in order to figure out if you and your partner share similar views and values.

1. Do you think that everything happens for a reason?
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2. Do you think that hard times make you bitter or better?
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3. Were you raised with any beliefs that you now reject?

4. Do you value money or close relationships more?
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5. What is one really positive value that your parents instilled in you?
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6. Who shaped a lot of the values you still carry?

7. What is a value of mine that you really admire?
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8. What is a value that you think the two of us share?
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9. How important is money to you?

His life goals

Knowing what your partner sees in his future is a great way to figure out if you two have long-term potential. If your vision for the future doesn’t align with his, then there is a chance the two of you have an expiration date, so making sure you two are on the same page early on is important. Find out the direction your boyfriend is headed by asking him the following questions.

1. Where do you see yourself in one year?
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2. Where do you see yourself in five years?
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3. Are you interested in creating a business together?

4. In what areas of your life do you have goals set right now?
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5. Is personal development important to you?
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6. How dedicated do you feel to improving yourself?

7. Are you good at following through when you set goals for yourself?
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8. What are some ways that you self-sabotage your own success?
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9. Is there anything I can do to help support you in reaching your goals?

10. What is one daily goal you could set for yourself right now that would greatly improve your life?

Hard questions to ask your boyfriend

Some of the best things in life don’t come easy, and answering these questions isn’t an exception. Waiting for the right time to ask these questions is important because they are deeply personal, and it may be hard for someone to share intimate details about themselves. Asking difficult questions may be a little uncomfortable, but your boyfriend’s answers will help you understand him in a much more meaningful way.

1. Does the idea of being in love scare you?
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2. Would you want to know the day or how you are going to die?
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3. Is there anything about you I don’t know and would make me question our relationship?

4. What do you think is the weakest part of our relationship?
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5. Is there anything about me that makes you question being with me?
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6. What would it look like if you fully lived up to your potential?

7. What is more important in a relationship, physical attraction or friendship?
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8. What is something that you have trouble accepting even if you know that it’s true?
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9. Are there any negative qualities about yourself that you’re worried you’ll never be able to change?

10. Are there any ways that you feel like your parents kind of messed you up?
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11. Is there anyone in your life that you hate?
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12. What is the most hurt you’ve ever felt by another person?

13. Have you ever been physically or emotionally abused?
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14. Is there anything you have ever wanted to tell me that you haven’t had the guts to?
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15. Do you think you could ever forgive me if I cheated on you?

16. What event has made you mature the most as a person?
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17. Do you find it easy to ask others for help?
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18. What is one thing that you know when it happens is going to break your heart?

19. If you died tomorrow, do you think you would die happy?
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20. When was the last time you stepped outside of your comfort zone? How did it feel?
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21. What physical feature of yours do you feel the most self-conscious about?

Weird questions to ask your boyfriend

Not all conversations need to be really deep. If you want some good questions that are sure to make your boyfriend laugh and allow the two of you to connect in a fun, non-sexual way, then these will be great options for you. Deepen your friendship and have fun laughing with your boyfriend by asking him these questions.

1. If you had a pet unicorn, what would you name it?
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2. Do you pee in pools?
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3. If you could be a cartoon character, who would you choose?

4. What’s something you love that other people think is gross?
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5. If you could have any animal as a pet, what would you choose?
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6. What is the best organ?

7. Do you wear clothes at home or hang out completely naked?
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8. Where was the worst place you’ve ever farted?
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9. Do you ever talk to yourself in the mirror?

10. How long do you think you’d survive a zombie apocalypse?
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11. If you had to kiss another guy, who would you choose?
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12. What is something that is always on your grocery list?

13. If you catch a fish, do you eat it or let it go?
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14. Would you ride on the back of my motorcycle?
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15. What do you usually do while you’re pooping?

Random questions to ask your boyfriend

If you want to keep your boyfriend on his toes and make him laugh, then these are great conversation starters for you to use. Not every conversation you have has to be deep and meaningful, so kick back, relax and enjoy asking your special someone the following random questions.

1. How often do you get in fights with strangers on the internet?
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2. Is there anything that you’re obsessed with?
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3. What is the best part about being a boy?

4. Would you rather eat McDonald’s or a salad?
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5. If you could only wear one thing for the rest of your life, what would you choose?
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6. What is the weirdest crush you’ve ever had?

7. If I had something on my face would you tell me?
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8. Do you think you could pull off glasses?
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9. Who is your favorite cartoon character?

10. If you found 5 dollars on the ground, what would you do with it?
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11. Would you rather live in a desert or Antarctica?
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12. If you could swap lives with one of your friends, who would you choose and why?

13. Would you get matching tattoos with me?
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14. If you could live as an animal for a year, what would you choose?
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15. Would you rather look like a potato or feel like a potato?

16. What is the worst thing about being a guy?
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17. Would you let me do your makeup?

Truth or dare questions to ask your boyfriend

As cheesy as playing truth or dare might seem, it’s actually a really fun and easy way to connect with your partner. Having fun in your relationship is an important part of keeping chemistry alive long-term. Asking simple, lighthearted questions like these can help you get to know each other better and have fun while doing so.

1. Your most embarrassing moment with a girl?
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2. How do you feel about your ex-girlfriend now?
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3. If me and your best friend were in trouble, who would you help first?

4. What’s a fantasy of yours that you’ve always been afraid to share with me?
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5. Is there anyone you stalk on social media?
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6. When was the last time you lied to me?

7. What do you do when you’re at home alone?
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8. What is a habit of yours that you think I’d be grossed out by?
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9. Is there anything about me that really annoys you but you don’t have the heart to tell me?

10. What did you think about me when we first met?
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11. What is the hardest thing about being a boy?
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12. Is there anyone you kissed while drunk that you regret kissing?

13. What is the weirdest dream you’ve ever had?
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14. What is the worst gift someone has ever given you?
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15. Are there any friends of mine that you don’t like?

16. What is my worst quality?
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17. If you could go on a date with any celebrity, who would you choose?
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18. On a scale from 1-10, how good do you think I am in bed?

Common questions and important considerations

How to know what questions to ask your boyfriend

If after reading this article you are wondering how to choose the right question for your relationship, then here are some things to keep in mind.

58% of men feel under pressure to be emotionally tough and feel that they can’t show any weakness.[3] This shows that when it comes to deep conversations about emotions, your boyfriend might enter the conversation feeling guarded and uncomfortable about expressing emotion and being possibly perceived as weak.

While speaking about deep, personal topics might be comfortable to you, it is possible that another person will not share this same level of comfort when it comes to opening up. What is appropriate to ask will depend largely on your specific relationship and how comfortable your partner is sharing intimate details about their life.

The lighter categories in this article are appropriate to ask in most situations and do not involve a lot of discretion, but when asking more personal questions, it is important to monitor your boyfriend’s reactions. If he is avoiding eye contact or his body language indicates he is feeling uncomfortable, then it is best to end the conversation and ask him how you can help him to feel loved and safe in that moment.

When is the right time to ask these questions?

Asking questions about your boyfriend is a generally good way to make him feel as though you are interested in getting to know him on a deeper level, and a lot of people feel very loved by this kind of attention.

When it comes to lighthearted questions, there is generally no ”‘wrong” or “right” time to ask them. If your boyfriend is feeling tired or like he doesn’t have the space to answer questions at that moment, then that is a boundary that should be communicated by him clearly and lovingly.

When it comes to more personal questions, it is important to be intentional about when you ask them. Generally, this should not be when your partner has had a long day or is in a noticeably bad mood. It is important to wait for a time when you feel like the two of you can connect without interruption and both feel safe to let your guard down.

If your boyfriend is blessing you by letting his guard down and letting you know more intimate details about himself and his life, make sure that you make listening to him your number one priority.

What to talk about with your boyfriend

When it comes to what to talk about with your boyfriend, it’s best not to overthink it. If you are nervous asking questions, start with light, fun conversation topics that feel more comfortable. As you gain more courage, you can begin asking more flirty and suggestive questions, and chances are your boyfriend will love it.

The important thing to remember here is that nothing is really that serious, and the experience of getting to know your partner is supposed to be fun. If you’re with someone that doesn’t appreciate you wanting to get to know them better, that’s not a “you” problem.

Why using questions to test your boyfriend can damage your relationship

If you have access to the internet, you have no doubt seen some of the toxic relationship advice that makes its way around platforms like Instagram and Tik Tok. While this advice may be funny, it can also be incredibly damaging to implement in your romantic life, and using questions that are designed to test your partner is one of the ways that you can ruin your relationship with a potentially great match.

No one likes to feel like people are asking them questions that are intended to be manipulative and coercive, least of all the person they are involved with romantically. When you play games with your boyfriend, it’s very possible that he will begin to feel as though you do not respect him, and it could severely damage the trust in your connection. It’s difficult to feel safe in a connection that doesn’t have a strong foundation of trust, and using trap questions to test your boyfriend is an easy way to erode your connection with him.

When it comes to love, there is no perfect question that you can ask to figure out if someone is right for you. Getting to know someone involves spending quality time with them and asking them questions from a place of love and genuine desire to better understand them. Spend more time paying attention to how you feel when you’re with your boyfriend and less time trying to mastermind the perfect question to test your compatibility.

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages SocialSelf’s scientific review board. Follow on Twitter or read more.

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