Simple questions to ask your boyfriend

325 Questions to Ask Your Boyfriend For Every Situation

What do men want? Each guy is different! These questions will help you learn what is important to your boyfriend and what he needs from you. 

Our 20 Favorite Questions to Ask Your Boyfriend 

Asking your boyfriend good questions can:

  • Help you get to know him better
  • Identify red flags early on
  • Strengthen the relationship
  • Deepen intimacy
  • Establish open communication 
  • Show you what he needs in the relationship

A guy needs to feel invested in the relationship and that you care about what he cares about. Once you know what he cares about, it will help you build a more genuine connection. 

Ask follow-up questions, and be willing to learn about new things. At the same time, be genuine in your interest. Don’t fake it just to appear more appealing! 

When you combine authenticity, warmth, and a healthy dose of attention, he’ll feel seen and heard by you. Not only that—he will probably find you more attractive as a result!

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Guidelines for Asking Questions

  • Remember—you’re asking questions, not conducting an interrogation. When you ask a question, lean forward and make eye contact waiting for the answer. Listen and interact with the response the way you would with your best friend. Nod, smile when appropriate, and mirror his verbal and facial cues. 
  • Use the questions as a starting point. Ask follow-up questions, and share your answers. 
  • Grab our list of questions to ask girlfriends, so he can ask you his questions.
  • Pay attention to nonverbal cues while he’s speaking. His cues might send you a different message than his words.
  • Always listen to his serious answers without criticism or judgment. Just like you, he needs to feel safe in the relationship. 
  • When asking fun and weird questions, be playful with your responses.
  • This isn’t a checklist!  Choose the best questions that resonate with you, and naturally ask them during conversations. 
  1. Who are you closest to in your family? 

This question can reveal much about his family dynamics and who he feels safest with. If he has a complex family or childhood, this question doesn’t feel as probing or complicated as questions like, “Tell me about your family.” or “Did you have a happy childhood?” 

You might also learn what makes him feel accepted or loved. Is he closest to his aunt because she always listens? Closest to his sister because she makes him laugh? Closest to his mom because she never dismissed his feelings? 

  1.  What’s your best quality? 

You might already have an idea of what his character qualities are, but you might be surprised by what he selects to share. The character quality that people value in themselves is often what they hope to find in others as well. If he says he is genuine, honest, or kind, you can bet that he’s looking for a woman who is genuine, honest, or kind. If his favorite quality is being masculine, dig deeper and discover what that means to him and why he values it.  

  1.  How Do You Most Feel Loved? 

Learning how he feels loved will give you a foundation to connect more deeply and effectively. It will also remove much of the guesswork on what he needs from you. 

You may think you’re showing him love, but if it’s in a way, he doesn’t value (or is even suspicious of) your relationship will have a hard time moving forward. 

On the other hand, once you start showing him love the way he needs it, you can make him feel secure and respected. 

  1. What do you feel makes a healthy relationship?

Find out what he views as healthy and his expectations for the relationship. You can also ask him who in his life has modeled a relationship that he admires. Follow up by asking why he admires their relationship and if he sees that happening for the two of you.

  1. What is your passion project?

Find out what matters to him and where he spends his time. When you learn what he’s passionate about, express interest in sharing that with him. Don’t forget to affirm his passion! He may have had girlfriends in the past who dismissed his ‘hobbies’ or belittled what he cared about. You have the opportunity to build him up and encourage him. 

  1. Who is the person in your life you can always count on?

Whether it’s his best friend from grade school or cool Uncle Pete, the person he can always count on holds an important place in his life. Ask him to tell you some stories of how this person was there for him, and as a result, you’ll learn some of his struggles, victories, and even regrets.  

  1. What’s something most people don’t know about you?

A fun question to ask allows him to share something personal about himself. He might give you a funny or a serious answer, but either way, this question can build intimacy in your relationship through self-disclosure.

  1. What is a weakness in other people that bothers you?

What a person views as a weakness is the area he will be critical and judgmental about. This is a fascinating question as it reveals what he has little patience for in others (and himself!). You’ll get a glimpse of what he values most with this answer. 

  1. What makes you angry?

Honey, you don’t want an angry man. It’s just a toxic timebomb. Everyone gets mad about different things, but if he’s prone to getting angry, especially out of proportion with the situation, don’t mess with that. 

  1. What is your favorite thing to do after work?

Does he always go out with the guys after work? Does he prefer to head home and relax on the couch? Does he work out at the gym or take the dog for a nightly run? 

Find out what he does to relax. This could indicate whether he is an extrovert who gains energy being around other people or is more introverted. You might also get a glimpse into how he deals with stress.

  1. What are your annoying habits? 

This is less about identifying his annoying habits and more about seeing how self-aware he is. Plus, you’ll get an idea of how serious his habits are. Leaving socks everywhere might be incredibly annoying, but it isn’t a deal-breaker. On the other hand, cursing or always joking in serious situations could be annoying habits that cause problems later in the relationship. 

  1. What do you love about your mom? 

Is he overly attached to mom, or one of those guys who have trouble respecting women? Get an idea of what you’re dealing with by asking him about his relationship with his mom. Listen for any bitterness, hurt, or overreliance because these can be red flags. 

Just because he has a mommy wound doesn’t mean you should dismiss him right out the gate! But be aware it could impact how he treats you, especially if this isn’t something he’s working to deal with.  

  1. What stresses you out?

Help him talk about his stress, and listen with empathy. If you don’t understand why something is a stressor to him, ask, “What stresses you most about that?” In the process, you’ll learn more about how he responds to his work and personal environment. Look for ways to encourage him when he’s feeling worn down. 

  1. What’s your perfect day?

While it’s usually the guys who plan the perfect date in movies, why not arrange the ideal date around his answer to this question? You’ll show him you were listening to what he said and that you don’t expect him always to be the one to make you happy. 

  1. How did your last relationship end?

If it was a toxic relationship or he’s still attached to his ex, you need to talk about it. Process these feelings openly and find out how you can both build a relationship that doesn’t repeat old mistakes.  

  1. Can we talk about our health histories? 

We don’t like talking about this with other people, but it’s essential to be open about past or present health concerns. This includes STDs (you have a right to know this information before being sexually active), mental health struggles, and other health concerns that could impact your relationship. 

  1. Tell me about your best friend.

You might get the same answer to this question as #6, “Who can you always count on?” but it might be completely different. While you may be hoping you’ll be his best friend, it’s healthy for you to have other friends outside of your relationship. 

You also need to know if he’s a lone wolf or if he’s capable of having healthy platonic relationships. 

  1. What do you feel is your most significant achievement? 

Go on, give him a chance to brag a little! Plus, you’ll learn about what he values in life. Then, ask him how that accomplishment made him feel and what he’s working towards now. Whatever his goals, let him know you believe he can do it.

  1. What are your political ideals?

This one can get heated. So, find out early what his stance is. If you don’t share those ideals, explore whether you are comfortable agreeing to disagree. A minor disagreement can be healthy, but you don’t want ongoing tension. Even if you disagree on a specific policy or party, see if you agree on the heart of the matter. You might have more in common than it seems on the surface. 

  1. I need your advice, can you help me with ____? 

Guys usually like to fix things. 

So surprise him by asking for his advice AND his help. Just make sure you ask for advice on something you want advice on! 

When you ask someone for help, it kicks in the Franklin Effect. In short, The Franklin Effect happens when you ask for help or favor, and it causes others to feel favorably towards you. You can thank Ben Franklin and another Legislator for discovering this little technique, which could strengthen your relationship with your boyfriend. 

Keep reading for 300 more questions to ask your boyfriend. Want the Short List? 36 Questions to Truly Know Your Significant Other

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Deep Questions to Ask Your Boyfriend 

Ask your boyfriend deep questions to spark… deep conversations. You’ll learn a lot about his thoughts, who he is, and how he perceives himself. 

  1. What makes you the best version of yourself? 
  2. What are things you do even though you don’t want to? 
  3. What does love mean to you?
  4. What’s your best quality? 
  5. What’s something you’ve always dreamed of doing but never have?
  6. What’s something we could change about our relationship to make it stronger?
  7. What makes us special or unique together?
  8. What do I mean to you? 
  9. What can’t you live without? 
  10. How have you changed in the last several years? 
  11. What makes you feel accomplished? 
  12. What do you think a good man is?
  13. What is something you’re afraid to lose?
  14. How do you know if you’re successful?
  15. What kind of dad do you want to be?
  16. What do you want to be remembered for? 
  17. What would you do if you lost your job? 
  18. If your family or friends didn’t approve of me, what would you do? 
  19. Are you an introvert, extrovert, or ambivert? How has that been both an asset and a weakness in your life? 
  20. What do you think is one of the most significant issues in our country today? 
  21. What keeps you awake at night? 
  22. If you could make a playlist of your life in high school, what songs would you put on it? 
  23. Have you ever been disappointed by your religion? What did you do to work through it? 
  24. Can you remember seeing your dad cry when you were growing up? How did you feel?
  25. What do you wish you’d had more of as a kid? 
  26. What do you think about X’s current event? 
  27. What would you change about the medical system in our country?
  28. What would you change about the education system in our state? 
  29. If you were a politician for a day, what would you do?
  30. If you could immigrate anywhere, what country would you choose? Why?  
  31. What is the best thing about our country? 
  32. Tell me about a time you had an opportunity you didn’t deserve? 
  33. What causes do you care about? Why? 
  34. Have you ever done NGO work? What was that experience like? 
  35. When was the first time you realized you needed a bigger perspective on the world? What changed for you? 
  36. What summer stands out the most in your memories?
  37. What was your coming-of-age experience? 
  38. When did you first feel like a man? 
  39. What fictional character do you identify with? 

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Fun Questions to Ask Your Boyfriend

Don’t limit yourself to only deep or serious questions! These fun questions will help him share stories and maybe even get you both laughing.  

  1. What’s the craziest thing you’ve ever done? 
  2. Tell me your favorite travel story. 
  3. How many places have you lived? What was your favorite place? 
  4. Tell me a funny story about your first car. 
  5. What do you always procrastinate doing?
  6. What’s your favorite song? Sing it for me! 
  7. What’s your favorite way to relax?
  8. Have you ever traveled outside of the country? Tell me about it! 
  9. What are your guilty pleasures?
  10. If you could travel anywhere in the world right now, where would you go and why?
  11. Where are you originally from? 
  12. What are some of your family traditions? 
  13. How did you spend your summer vacations?
  14. What was your favorite subject in school? Did you have a favorite teacher? 
  15. Do you have a pet? If not, would you ever want one?
  16. If you had a pet tiger, what would you name it? 
  17. What was the best sporting event you ever attended?
  18. What was your proudest sporting moment? (If they play a sport)
  19. Are you mentoring anyone? (e. g., coaching a team, teaching a skill, volunteering, etc.)
  20. What was your best day? 
  21. Have you ever sung karaoke? How good or bad was it? 
  22. Who is your hero or someone you’ve admired for a long time?
  23. What do you like to do on a rainy day?
  24. Do you prefer to stay home or go out on the weekend?
  25. What was your biggest adventure? 
  26. What was your biggest travel mishap?
  27. What was the dumbest thing you said to a crush? 
  28. What is your favorite holiday?
  29. What was the best or strangest gift you ever got? 
  30. If someone told a joke and no one laughed, what would you do? 
  31. What did you like to do during recess? 
  32. Did you love or hate P.E.?
  33. Do you play an instrument or sing?
  34. What’s your favorite city? 
  35. What extreme sport have you always wanted to try? (bungee jumping, parkour, paragliding, etc.)

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Cute Questions to Ask Your Boyfriend 

Up the cute factor and focus on the warm and fuzzies. Help release the happy hormones by talking about good memories and positive emotions. 

  1. Will you teach me (insert passion or hobby)?
  2. What can I do to make you feel better after a bad day?
  3. What is your happiest memory? 
  4. What is the kindest thing you’ve ever done?
  5. What is the kindest thing someone else has done for you? 
  6. Describe your dream house. 
  7. If you’re sick, do you want someone to care for you, or do you prefer to be left alone?
  8. Will you promise to fix my hair if it gets messed up by the wind? 
  9. What stuffed animal did you sleep with as a kid? Do you still have it?
  10. What is the cutest couple you’ve known?

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Serious Questions to Ask Your Boyfriend

Early in your relationship, start asking serious questions to learn what he values and believes. You don’t want to be 6 months into a relationship and suddenly discover alpha females threaten him or that you regularly do things that get on his nerves (he’s just never told you!).  

  1. What makes you the happiest?
  2. How can I support your interests? 
  3. Do you hold grudges?
  4. How would you describe your family? 
  5. Tell me about your relationship with your parents and siblings. 
  6. What do you want to improve or change about yourself?
  7. Do you have any regrets? Would you go back and change those things if you could?
  8. What terrible experience taught you a valuable lesson?
  9. How do you deal with failure? 
  10. What are some things that offend you?
  11. What gets on your nerves?
  12. Do you love your job? If so, why? If not, why do you stay there? 
  13. What do you need when you’re upset? Space? Talking it out? Something else?
  14. What’s something you’ve been scared to ask me? 
  15. Where do you see our relationship going? 
  1. What mistake have you made in a past relationship that you don’t want to repeat?
  2. Where do you see yourself settling down? / Will you be here long?
  3. Are there any strong women in your life? How do you feel about powerful/successful women? 
  4. Do you want children?
  5. Does our age difference bother you? (If relevant)
  6. What should never be joked about? 
  7. What does friendship mean to you?
  8. How do you handle conflict? 
  9. Do you have children? If so, what does co-parenting look like for you? 
  10. Who do you live with? 
  11. What’s your relationship like with your dad? 
  12. Are you single? Is there anyone out there who thinks you’re their man? 
  13. Do you have any significant responsibilities? 
  14. What is something you’re working on to become a better person?
  15. How are you? (Ask this question and mean it!) 
  16. What are the things you spend the most money on? 
  17. When you break up with someone, how do you do it? 
  18. If one of my friends flirted with you, would you tell me? 
  19. Have you ever broken the law? 
  20. Do you have a mentor? What is the most important lesson they taught you?
  21. Do you believe people should only date within their socio-economic status? 
  22. Who do you think should pay for dates? 
  23. How do you feel about surprises? Do you like to be surprised?
  24. Have you ever been married? 
  25. Have you ever been engaged?
  26. What are you doing to care for the planet?
  27. Do you have any serious allergies?
  28. Have I ever made you feel cut down or belittled in front of people?

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Cultural Questions to Ask Your Boyfriend

Are you dating someone from a different culture? That could be either religious, ethnic, or even socio-economic. If so, you will have differing worldviews, values, customs, and expectations. Ask him questions, but also ask him to teach you, even when you don’t think to ask. 

Some of these questions are more appropriate later in the relationship and may be more or less relevant depending on the differences between your two cultures. 

  1. Is there anything I should know about interacting with you in front of your family? 
  2. Does your culture have a hierarchy?  
  3. What values are most important in your culture?
  4. What’s your favorite faith tradition or cultural tradition in your family?
  5. What are the most critical parts of your culture that you want me to know about?
  6. What expectations will your family have for us?
  7. How should I interact with your parents? What should I call them?
  8. How can I show respect to your family?
  9. What things might I do unintentionally that would offend you?
  10. Can you teach me to eat a traditional meal without causing offense or looking stupid? 
  11. Will I be expected to help prepare or clean up after a family meal?
  12. Where should I stand/sit? 
  13. What should I do when I first meet your family? 
  14. What was it like growing up in your culture? 
  15. Is there hostility between our cultures? Do you ever feel that hostility/prejudice from my friends or family? Will your family feel hostility/prejudice towards me?
  16. How do you want me to express when I disagree with you?
  17. Are there parts of your culture that I shouldn’t try to assimilate because it would be offensive? 
  18. Are there prayers I should or shouldn’t expect to take part in? 
  19. How can I say no to your family without offending them (e. g., if they offer me food I don’t like, offer a gift that is offensive to my culture/religious belief, etc.)
  20. Do you celebrate holidays common to my culture? Do you celebrate holidays common to your culture? Am I allowed to be a part of those celebrations? 
  21. Are there any foods or drinks I should know about that are restricted by your religion? 
  22. Can you teach me some basic phrases in your first language?
  23. Can you teach me some basic phrases from the language your family speaks? 
  24. Can you teach me to make your favorite ethnic food? 
  25. What food does your family typically make for sick people in your culture? Can you teach me how to make it? 
  26. How can we make our traditions? 

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Romantic Questions to Ask Your Boyfriend 

Talk openly about your feelings, your needs, and your expectations. Regarding relational intimacy (physical or emotional), it’s essential to talk about it beforehand.

Be clear on:

  • Expectations
  • Boundaries
  • Personal and religious beliefs 

As well as what you both see as being healthy, respectful, and morally responsible. Get the conversation going with these important relationship questions.

  1. What do I do that makes you feel loved?
  2. How can I make you feel more appreciated? 
  3. What are you like as a boyfriend? 
  4. Why do you want to be in a relationship with me? 
  5. What do you think is most important to have in common with someone you’re dating? 
  6. Do you believe in monogamy? How would you define that? 
  7. Once you get married, if you weren’t happy in the relationship, would you break up or work through the difficulties? 
  8. What is your view on sex in long-term relationships? 
  9. What are your views and beliefs about physical intimacy? 
  10. How does your culture or religion view sex?
  11. What makes you think your partner wants more physical intimacy? 
  12. How do you feel about public displays of affection? 
  13. What do you consider cheating? 
  14. Have you ever cheated? 
  15. Have you ever been cheated on?
  16. I expect you to: ask first, stop if I say no, wait for verbal consent, let me lead, wait for me to meet you halfway, etc. (fill in the blank with what you need/want). Are you willing to respect that? 
  17. How do you like to show love?
  18. How do you like to receive love? 

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Flirty Questions to Ask Your Boyfriend

Try out these flirty questions to spark attraction. 

  1. Would you braid my hair? 
  2. Will you dance with me right now? 
  3. What sets me apart from other women? 
  4. What color best describes me?
  5. How is your life different with me in it? 
  6. Will you help me pick an outfit for tonight? 
  7. How many times did you want to ask me out before you finally did?
  1. What was our first kiss like for you?
  2. Will you cook for me? 
  3. I want to cook for you. What would be your ideal meal? 
  4. What do you think about me during the day?
  5. If I was sad, what would you do to cheer me up?

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Random Questions to Ask Your Boyfriend

From silly to serious, here are additional questions to keep the conversation going.  

  1. Are you a night owl or an early bird?
  2. Books or movies? 
  3. What is your favorite book?
  4. What is your favorite movie?
  5. Do you have a favorite food? 
  6. Who is your favorite team? (basketball, football, soccer, etc.)
  7. What are you like when you’re grumpy and tired?
  8. What’s your favorite dessert?
  9. Would you rather homestead or be a financial advisor? 
  10. What food do you always crave? 
  11. Who do you spend the most time with?
  12. What is one place you never want to go again?
  13. What is one place you’ve always wanted to go back to? 
  14. How long should people date before meeting their parents? 
  15. Do you have any irrational fears or phobias? 
  16. Who inspires you? 
  17. What’s something most men dislike that you love?
  18. Tell me about your grandma.
  19. Do you prefer to eat out or cook for yourself? 
  20. How would your friends describe you?
  21. Would you rather be right or happy?
  22. What was your most embarrassing moment? 
  23. What was your childhood nickname?
  24. What is your silliest pet peeve?

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Weird Questions to Ask Your Boyfriend

These questions are suitable for a laugh and making fun icebreakers when you’re on a date.  

  1. What conspiracy theory are you tempted to believe? 
  2. What’s your nighttime ritual? 
  3. Have you ever slept in your shoes? 
  4. Do you sleep with your mouth open?
  5. What was the weirdest place you ended up sleeping? 
  6. Do you snore?
  7. Will you tell me if I have food or lipstick on my teeth?
  8. Would you rather be a puppy or a kitten? 
  9. Would you rather own a baby elephant named Jeff or a fluffy bunny named Snookums?
  10. Did you want to be an astronaut when you were a kid? What did you want to be?
  11. What is the weirdest thing you’ve put on a sandwich?
  12. What is the weirdest thing a coworker said to you? 
  13. What was the strangest wrong number text you’ve received?
  14. What flavor of ice cream are you? 
  15. Do fish have necks? 
  16. Are chickens a bird since they don’t fly? 

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Intimate Questions to Ask Your Boyfriend 

Keep these more intimate questions for when you’re moving towards a committed long-term relationship. Some of these may be asked earlier, but most of these questions are very personal and will require closeness and trust.

Healthy relationships are ones where both people are willing to explore and understand the hurts and experiences of the other person. Instead of toxic behavior patterns, learn how to support each other emotionally and develop healthy communication.

If your boyfriend isn’t ready to talk about some of these things (such as adverse childhood experiences), respect their boundaries, but let them know these questions are essential and need discussion.

When you ask these questions, be prepared to listen without judgment or criticism; only ask questions you’re also willing to answer.    

  1. When was the last time you cried? 
  2. What are you afraid of?
  3. What makes you feel sad?
  4. Did you feel love and support from your parents growing up?
  5. Have you ever been in therapy?
  6. What did you learn about relationships in therapy? 
  7. How do you regulate your emotions? 
  8. What triggers you? 
  9. What are your coping mechanisms?
  10. Is there a past relationship that you still feel hurt or angry about? Tell me about it?
  11. What is your earliest memory?
  12. What relationship causes you the most stress? 
  13. What is your worst memory? 
  14. What do you most regret not saying to someone? 
  15. What is something you wish you hadn’t done? 
  16. What is the best decision of your life?
  17. What was the hardest decision of your life? 
  18. How do you approach finances? Do you have debt? What are your financial goals?
  19. How would you feel if I earned more money than you? 
  20. Aside from parents/guardians, who shaped you the most growing up? 
  21. What signs are you getting stressed that others don’t pick up on?
  22. How can we communicate when either of us needs space? 
  23. What makes you feel disconnected from me? 
  24. What was your relationship with your siblings growing up? Was there favoritism?
  25. What are some terrible family traits you are working on so you don’t pass them down to your children?
  26. How many sexual partners have you had? 
  27. What are your retirement plans? 
  28. What are your thoughts on how to raise/discipline children?
  29. What do you think each person’s role is in marriage?
  30. How will we spend our holidays? 
  31. How would we make decisions as a couple?
  32. What role will your family play in our relationship?
  33. If we get married, how much say will your parents expect to have in raising our kids? 
  34. Have you lost anyone close to you? 
  35. How can we both communicate more openly? 
  36. Who can I go to for help or advice about you? 
  37. What are you afraid people will think about you? 

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Questions to Ask Your Boyfriend over Text 

Texting is an excellent opportunity to talk about less serious things and engage in witty banter. Be playful when you respond to his answers and use emojis so he knows when you’re joking.

  1. You can only rescue one thing from a 🔥. Your favorite 👞👞, this week’s groceries, or your work laptop. These are your only options. Which do you choose? 🤷🏾‍♀️
  2. What emoji would you use to describe me? 
  3. Do you remember the first day we met? 
  4. Would you rather eat Mexican 🌮 or Korean 🍚??
  5. Would you instead go to a ⚾ game or art museum?
  6. If you could only eat 🌭 or 🍔 for the rest of your life, which would you choose?
  7. This may be a deal-breaker, but what is your stance on the ever-controversial subject… Pineapple on pizza? Yes or no?
  8. What do you think is my favorite food? 
  9. What do you think would be my ideal date night? 
  10. What’s your favorite movie that I would be surprised you like? 
  11. What’s your favorite movie of all time? 
  12. What movie did you watch every chance you got when you were a kid? 🧒
  13. What makes you feel comfortable around someone? 
  14. Did anything weird or funny happen to you this week?
  1. Tell me your worst dad joke! 
  2. I’m sorry your day was horrible. Is there anything I can do to improve it? 😙
  3. Would you rather have stability or adventure?🤠
  4. ⛰️ or 🌊?
  5. 🛋️or a day in the city? 
  6. Can you teach me to 🎣? 
  7. Would you rather skip work or skip your gym workout? 💪💪
  8. What’s your favorite magazine? 
  9. What’s your favorite 📕? 
  10. Dark, milk, or white chocolate? Do you like nuts in your chocolate? 🍫
  11. What’s your favorite scent?
  12. What’s your hidden talent? 👀
  13. Do you have any plants? 🌱 What is the longest you’ve kept a plant alive?
  14. What can your friends always count on from you? 
  15.  What is the longest time you’ve gone without taking a shower? 🛀
  16. Are you a foodie? 🥐 What were the best tacos you ever ate? What made them so unique?

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Questions to Ask Your Boyfriend about You

Curious what he thinks about you? Just come right out and ask him! He might not naturally offer this information, so help him express his feelings by asking specific questions.  

  1. When did you first realize you liked/loved me? 
  2. What was your very first impression of me? 
  3. What song makes you think of me? 
  4. What’s something I do that you love? 
  5. What do I do that makes you feel rejected or unloved? 
  6. What’s your favorite thing about me that’s not a physical feature?
  7. How can I be a more supportive girlfriend? 
  8. If one of your friends flirted with me and I told you, what would you do?
  9. What makes me beautiful to you?
  10. Do you smile when you think about me? Why?  
  11. What’s your favorite outfit that I wear? 
  12. Do you like it when I wear my hair up? 
  13. How would you handle another guy hitting on me? 
  14. How have you seen me grow in the last several months? 
  15. Do you think I’m living up to my potential?

Does your boyfriend need a list of questions too? Check out 315 Questions to Ask Your Girlfriend.

60 Questions to Ask Your Boyfriend to Bring You Closer

60 Questions to Ask Your Boyfriend to Bring You Closer

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In terms of a romantic partner, it’s wonderful to find someone with whom you can share a comfortable silence. Someone who can sit by your side while you think, or not think. Someone you can just be present with. But, of course, you don’t want comfortable silence all the time. For those moments when you want to get closer through conversation, we’ve gathered a list of 60 illuminating questions to ask a partner in order to get to know them a little better.

1. Do you want children?

2. Do you want to get married?

3. What do you think the most important element is in maintaining a relationship?

4. What is the No. 1 thing you look for in a partner?

5. What is your favorite thing to do on a date?

6. What is the most romantic place you’ve ever visited?

7. If you want children, how many children do you want?

8. Have you ever been cheated on?

9. What is the best gift you’ve ever given a partner?

10. What is your favorite love song?

11. What is your favorite date night movie?

12. Would you prefer to cook a romantic dinner, or do the romantic dishes?

13. When do you think is the right time to say “I love you”?

14. Do you think fighting in a relationship is healthy, or do you think it should be avoided?

15. What is something important you’ve learned from another couple?

16. What is a mistake you’ve made in a relationship in the past that you don’t want to repeat?

17. What do you think is your best attribute as a boyfriend?

18. Are you friends with your exes?

19. Have you ever had your heart broken?

20. How can you tell you’re really comfortable with someone?

21. Do you have any hidden talents?

22. If you could meet one celebrity, who would it be?

23. If you could relive one day in your life, what day would you choose?

24. Would you ever go skydiving?

25. Have you ever been afraid of a ghost?

26. What was your best Halloween costume?

27. What was your favorite school lunch as a kid?

28. What is your favorite Simpsons joke?

29. If you could live inside the world of one TV show, which would you choose?

30. If you have a billion dollars, what do you think your life would be like?

31. What is your favorite scent?

32. What is your favorite outfit?

33. If you could change your name to anything, would you change it, and what would you change it to?

34. If you could suddenly be very good at something without having to put any effort into getting good at it, what would it be?

35. What is a book or movie you’ve always lied about having read or seen?

36. What career do you wish you could have?

37. If you could go to the moon, would you?

38. Do you think aliens exist?

39. Do you think you would do better or worse on the SATs if you had to take them now?

40. What is your favorite meal of all time?

41. What cartoon character do you think is the hottest of all time?

42. What is your most controversial movie-related opinion?

43. Do you think dogs go to heaven?

44. What is the hottest you’ve ever looked?

45. Who do you think is the MVP, LeBron or Giannis?

46. If you could change one thing about me what would it be?

47. Who do you think has it harder: men or women?

48. Who is the most beautiful person you can think of?

49. Can you explain to me the process of menstruation and why it occurs?

50. Can you tell me what accounts for the sun appearing to rise and set?

51. Can you name ten authors who are not men?

52. Do you still text with any of your exes?

53. Have you ever cheated on anyone, and do you feel the phrase “once a cheater, always a cheater” is true or false?

54. How do you feel about Elizabeth Warren and why?

55. What is the best outfit you’ve ever seen me wear?

56. What is the funniest thing I’ve ever said to you?

57. What is your favorite thing about me?

58. Do you think I’m stronger in my career or stronger in my personal life?

59. Would you rather be a stay-at-home parent or a working parent and why?

60. Does the idea of someone having dinner on the table for you every night at 6 p.m. sound good to you? Why or why not?

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A Long List of Questions to Deepen Your Relationship

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300 questions to your boyfriend

Getting a lot of one word yes/no answers from your boyfriend? If you are familiar with this, then we will help you talk to him!

Guys can be notoriously reserved when it comes to talking. The questions that you will find below will help you start a conversation, and further establish a connection with him. Remember: do not give up, ask questions and encourage him to give you more detailed answers.

Of course, there are guys who are more than happy to talk about themselves and will talk over and over again. During a conversation with one of these guys, these questions will help you get to know him better and understand who he really is.

Remember that every guy is different. Some questions are great for some guys, but not at all for others.

📖 Content:

  • Best questions
  • Funny questions
  • Personal questions
  • Questions about his past
  • Questions about people

You will have to choose which questions you think would be best for your boyfriend and which questions you really want to know the answer to. So, with all that, let's get started!


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The best questions to ask your boyfriend

1. What would your ideal day be like?

That's a good question, because every guy has an answer. Therefore, this is the perfect start for a conversation, after which you will learn more about what he likes to do.

If you can do what he likes (and vice versa), then both of you will have much more fun with each other.

2. What did you learn too late?

This is a question from a distance, after which you will know what regrets he has. What would he like to do or learn but never did? This will give you an idea of ​​what he wants in the future.

3. What are your complaints about yourself?

This one will let you know what his standards are. After all, if he has standards, most likely he expects other people to meet these standards.

Also, if he is hard on himself in many ways, he is more likely to be successful. If he is soft to himself, then most likely he has no desire to improve himself.

4. How often do you feel completely exhausted?

This question is a good indicator of how stressed he is. You can ask what makes him tired, and also find out what he worries about the most.

N e w !


5. If money didn't matter, where would you live?

This is a great question to see if you're a good match. If you both want to live in similar places, this is definitely a good sign. But if he wants to live in the countryside in a cold climate, and you want to live in the city and in the warmth, then this does not bode well. This is good to know if you plan to be together for a long time.

6. Who was the most toxic person you knew?

We all know people who make the world around them worse. After this question, you will find out what your boyfriend considers the worst of the worst in people.

You may both despise the same aspect of a person, or you may not. Either way, you'll find out what behavior he despises.

7. What were the last two books you read?

Does your boyfriend read? Find out by asking this question. If you are a voracious reader and he is not (or vice versa), this can be a problem. But if you both read the same amount, then you have nothing to worry about.

📖 We offer you: Questions about best friends: get to know them even better

And who knows, maybe this way you will find out about a cool new book.

8. What are your habits that annoy other people?

Yes, annoying habits. You will want to know about them. After all, if the two of you live together, these annoying habits will quickly turn from cute to frustrating. We all have annoying habits, and feel free to warn him about yours.

9. What makes you nervous?

Being nervous is a common human trait. So why not find out what makes your boyfriend feel uncomfortable? It is highly likely that this may be public speaking. But if possible, press it for more examples.

10. What makes you more angry than it should be?

This is a really important question. You want to know what pisses him off so you can avoid it. And if you can't avoid what makes him angry, you may need to find a new boyfriend. This also applies to you - if you are often angry with him, then with a high probability, you will want to reconsider your relationship. Because when there is too much anger in a relationship, it is incredibly toxic.

📖 We offer you: 100 questions to ask your girlfriend

11. What movie was so sad that you will never watch it again?

This is a great question to learn a little more about his emotional side. You will be able to see what is really suffocating him. You will also be able to check if he is emotional at all or not.

This is good to know anyway, because if movies don't make him emotional, then don't expect him to openly talk about his emotions in the future.

12. What are the two most important lessons you learned from previous relationships?

The main thing is not to be jealous. Yes, he had partners in the past. And these relationships are worth hearing about, because you can discover a lot for yourself.

You can find out what he expects from you based on the experience of previous relationships. You can also learn what to expect from him and how he acts when things don't go well.

13. What disgusting and unhygienic things do people who annoy you do?

So how clean and hygienic is your boyfriend? If you're going to end up taking your relationship to the next level, it's better to find out sooner rather than later.

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Basically, if this list is long, it means that he is a fairly clean person. If he just shrugs and says, "I don't know," then he's probably pretty dirty and unkempt.

14. Do you have a habit that you rarely see in other people?

We all have strange habits, and it's time to learn about it! Just remember not to be overly judgmental. After all, you probably also have some strange habits.

15. What do most people overestimate or underestimate about you?

This question is not so much about how other people see your boyfriend, but how he sees himself. You'll find out what your boyfriend thinks about how the world sees him, and how that contrasts with how he sees himself.

If his answer sounds strange, then this is a bad sign. If he sounds modest, then this is probably a good sign.

16. What should you do but never will?

This is a slightly odd question that can give you many answers. He's great for an interesting conversation starter because he's likely never been asked about it. But whatever the answer is, it will probably be quite interesting and instructive.

17. What was the best thing about raising your parents when you were growing up?

Ah, family. This is sometimes a sensitive topic, but you can learn a lot about someone by learning about their childhood.

📖 We offer you: 250+ questions for a guy: Get to know him.

Just remember to let him talk, don't make assumptions, and never treat his family negatively. People quickly become defensive when you speak ill of their family.

18. What do you most expect from aging?

This will be an interesting question for your boyfriend, because you will get either a funny answer or a serious story about how he wants to live after retirement. In any case, this is a great question.

19. What is the biggest sign of a person's weakness?

This is a really interesting question. His answer will tell you a lot about how he sees the world around him.

In fact, whatever the sign of weakness is, it will be what he will find fault with the most. And the opposite of this sign of weakness will be what he really admires and aspires to be.

20. What did you really try to love but couldn't?

Seeing who made him love something, you can see who he is trying or tried to please. You can also see how ready he is to confront this person or group of people. In addition, you will learn more about what he likes and what not.

21. What makes you different from most people?

A great question to ask your boyfriend who will show you how he feels, how he fits into society. If his answer contains many differences, he probably considers himself an outcast. If he has nothing to say, then he feels that he fits well into society. There is nothing wrong with either answer.

👉 We offer you: ❤️ Questions 99+ couples Trivia

22. What was the best mistake you made? A mistake that turned out to be really successful.

This question won't give you much information about your boyfriend, but it's a really entertaining question. You may hear an interesting story. Who doesn't love good stories?

23. If you were to drop everything and go on a trip, where would you go?

This question is similar to the question “where would you live” above. But instead of finding out where your guy wants to live, you can find out what kind of vacation he likes.

It's always good if you both like the same things. This means you have more things to do together and more things to talk about.

24. What are the most courageous and, conversely, the least courageous things that you have ever done?

This is a fun question that could lead to some cool and interesting answers. You can also find out how seriously he takes the concept of masculinity and what that concept means to him.

25. How do you feel about animals, domestic and wild?

It's a good question to ask for the simple reason that if one of you hates animals and the other loves them, then when you move in together, one of you will be unhappy. This is good general information that can lead to a cool and long conversation.

We offer you: 250+ questions to get to know someone

Fun questions to ask your boyfriend

  1. How often is your brain on autopilot?
  2. What do you think aliens will look like?
  3. Which site does not exist, but should exist?
  4. What inedible thing would you like to eat?
  5. Where is the craziest place you have ever danced?
  6. How should the toilet paper hang, roll end facing out or in?
  7. What is the spiciest thing you have ever eaten?
  8. What stupid thing are you proud of?
  9. What unnecessary products or services do you consider necessary?
  10. What's the best conspiracy theory you can come up with right now?
  11. If a job/career had slogans, what would they be?
  12. What do people really need to relax?
  13. What is the nastiest thing you have drunk?
  14. What hairstyles will go with certain characters?
  15. What does your brain do when you think about the thought process?
  16. If flowers had a taste, what would each color look like?
  17. What fictional villain made you really hate?
  18. What's the best stress reliever you can buy/make for less than $20?
  19. How often do you enter a room and forget why you entered the room?
  20. What is the strongest animal you can defeat with your bare hands?
  21. How would you like to die if after death you are forever placed in a room with people who died in the same way?
  22. What will an amusement park filled with your biggest fears be like? What attractions will be there?
  23. What would an amusement park be like, designed specifically to make you happy?
  24. What would you never want to know about how it's made and how it works?
  25. What names have been ruined for you because you knew someone terrible with that name?
  26. If you had a remote control to control any type of machine, what would you use it for?
  27. What are you doing in an incredibly inefficient or pointless way that you keep doing because you've always done it?
  28. What's the coolest thing scientists could discover while exploring the ocean?
  29. What's the funniest/weirdest thing they told you while drunk?
  30. If you were allowed to make a billboard in the center of your city, what would it be?
  31. If you had complete genetic control over plants, what would the coolest tree look like?
  32. What condiments do you keep in the fridge and what do you leave in the cupboard/pantry?
  33. What non-traditional ice cream toppings do you think would be great?
  34. How much ice cream should I put on a cone?
  35. If animals were as smart as humans, what kinds of jobs would they be uniquely qualified to do?
  36. Do fish have necks?
  37. Think of the best duel. Who will he be between?
  38. If everyone in your country could hear you at the same time, what would be the phrase that would make most people instantly hate you?
  39. If you were forced to take part in a dance competition, what song would you choose to dance with?
  40. You have unlimited desires, but every time you make a wish, what you love most is erased and disappears from the world. How many wishes will you make, and what will you make? (And no, you can't wish for things not to disappear after your wishes)
  41. What crazy things would you do if you were ever rich?
  42. How would the world be different if there were health potions?
  43. What did you Google last?
  44. What prank do you do regularly?
  45. What is the strangest text or phone call you have received by mistake?
  46. If you were given immortality, but on one condition, what condition would that prevent you from accepting immortality?
  47. If you could change your name, what epic name would you choose?
  48. Why do you think we dream?
  49. If you could change gender for a period of time of your choosing, would you do it? And if so, by how much?
  50. What event from the past would you most like to see recorded?
  51. What cool idea would you like to implement if you had enough money?
  52. If you were on a chase, what song would you like to listen to on the radio?
  53. If you had a cult, what would it be like?
  54. What non-military veteran are you?
  55. What routine work do you fear the most?
  56. If wars were abolished, what would be the most interesting way for countries to resolve their differences?
  57. What is legal but still feels illegal?
  58. What rarely works the way it should?
  59. What should be the next shoe promotion?
  60. What product shocked you that no one thought of making a better version?
  61. If you could make a candle with any scent, what would it be?
  62. If you could place a curse on your worst enemy so that any household item emits a blood-curdling scream at random intervals, what item would you choose for such a curse? (The curse will switch to a new version of this item if they buy a replacement. )
  63. What would be the first thing you would do if you gained the ability to fly?
  64. Where and when did you fart at the most inopportune moment?
  65. In what era of the imaginary future would you like to live? (For example, as in 1950-k, where there are many twists and sparkles)
  66. What would be different if it were socially acceptable to say anything openly and frankly about everything?
  67. What is the coolest flag to use?
  68. What band would be cool to see live if their name literally described the band? (i.e. if you take Guns and Roses, you would literally see roses and guns on stage)
  69. If you had a secret lair like Batman or Superman, what would it be like?
  70. What do you like least about the activity you love the most?
  71. If you were a play figure, what objects or clothes would you be with, and what phrases would you say?
  72. If you could do something first, what would be your achievement?
  73. How well do you think you would survive if you were lost in the woods for two weeks?
  74. Which label would you like to use?
  75. What do you like to spend your time on the most?
  76. What is your dream car?

Personal questions to ask your boyfriend

  1. What are you afraid of in the future?
  2. What scares you the most about yourself?
  3. What is the worst dream you have ever had?
  4. What makes you overly emotional?
  5. What is the fastest way to make you angry?
  6. What event made you a more mature person?
  7. What's on your to-do list?
  8. What is the most difficult truth you have ever encountered?
  9. How would you like your funeral to be?
  10. What makes you the happiest?
  11. What would your personal hell be like?
  12. How gentle are you?
  13. What routine task have you mastered and can do perfectly?
  14. What creepy thing do you do on a regular basis?
  15. What quirks does your body have?
  16. What harsh truth about yourself can you tell me?
  17. How many bad things happen to you because of you?
  18. What is it like to be you?
  19. When did you really try your best - just your best - and it still wasn't enough?
  20. When are you really you?
  21. If your life were a book, what would be the title of the chapter of this period of your life?
  22. What incredibly common life experience did you miss out on?
  23. What steps would you take to fulfill your lifelong dream?
  24. When are you a snob?
  25. What do you want written on your tombstone?
  26. What would it be like if you reached your full potential?
  27. How curious are you?
  28. Are you lucky?
  29. What is your favorite song?
  30. How do you deal with procrastination?
  31. What weird things are you into?
  32. How would you change your appearance if you had the opportunity?
  33. How easily do you change your mind?
  34. How do you care? Are you caring?
  35. Under what circumstances did you feel the most lonely?
  36. What makes you feel alive?
  37. How well do you think you can read the emotions of others?
  38. What makes you interesting?
  39. Who makes you feel uncomfortable when you are around?
  40. In what situations are you different from yourself?
  41. What do you value most?
  42. What sounds fill you with fear?
  43. Which word describes you best?
  44. How nervous do you think you are?
  45. What are you really obsessed with?
  46. Who or what is holding you back?
  47. How often do you get into arguments with people on the Internet?
  48. How adventurous are you?
  49. What do you want out of life?

Questions about your boyfriend's past

  1. What were the turning points in your life?
  2. What is the most painful message you have ever received or sent?
  3. What event has returned to you from your past and is haunting you?
  4. What did you hide from your parents?
  5. What was the most embarrassing moment you had at school?
  6. What was the smartest thing you did as a child?
  7. What unique and unusual games or activities did you play as a child?
  8. What's the weirdest thing you've seen at work?
  9. What was the worst injury you had as a child?
  10. The moment you were most famous?
  11. Have you ever stolen anything?
  12. How was it expressed when you were the coldest?
  13. If you could go back and change only one decision you made, what decision would you change?
  14. When was the time when you gave up on caution and just decided to do something?
  15. If your whole life was recorded but you could only choose one hour to watch, what scenes would you go back and watch?
  16. What is the most memorable call you received or made?
  17. What places have you been to but can never go back?
  18. What movie title best describes your life?
  19. What changed you for the better, and what changed you for the worse?
  20. Who did you intentionally remove from your life?
  21. What did you do in the past that people remember over and over again?
  22. Who is the nicest person you have ever met?
  23. Where is the most interesting abandoned place you've been?
  24. What were your favorite children's books?
  25. What is your most beautiful memory?
  26. What do you still cringe at when you think about what you did when you were younger?
  27. How much have you changed in 5 years?
  28. What did/didn't you say that you regret?
  29. What story about you is told by most people?
  30. What is your worst gag story?
  31. What is the most American thing you have ever done? (Regardless of whether he is an American or not).
  32. What is the most risky thing you have ever done?
  33. When was the last time you were really wrong?
  34. What bridges have you burned?
  35. What is the most uncomfortable thing you have to tell someone?
  36. What is the most memorable vacation you have taken?

Questions about people in your boyfriend's life

  1. How well do your family members get along?
  2. Who in your life has the most positive outlook on life?
  3. What was your closest friendship that broke up?
  4. What stupid things did you convince your friends to do?
  5. What is the most embarrassing thing someone has told you about?
  6. Who is most likely to be a serial killer in your life?
  7. What happened to your best friend from elementary school?
  8. How often do you talk to members of your extended family (grandparents, aunts and uncles, cousins)?
  9. What scandals have occurred in your circle of friends?
  10. Who is the black sheep in your family?
  11. Who is the most difficult person you have to deal with on a regular basis?
  12. What are the three most important things you learned from your parents?
  13. Who in your life is full of unreasonable confidence in his opinion?
  14. What secret is someone hiding from you, but you already know everything?
  15. What plausible rumor can you come up with right now about a celebrity or a friend in your circle of friends?
  16. When did you think you knew someone but they turned out to be a completely different person?

Relationship questions to ask your boyfriend

  1. What is the best marriage or relationship advice you have ever received?
  2. What is your number one rule in relationships?
  3. What is the role of a wife?
  4. How do you get an idea of ​​what a good relationship is?
  5. What could be the best and worst things about a long-term relationship?
  6. Who has the healthiest relationship in your life with their significant other?
  7. What do you think are the pros and cons for you as a relationship partner?
  8. How much work does a couple have to put in to have a strong relationship?
  9. How serious does it have to be before a married couple goes to a family psychologist?
  10. What did you learn about relationships from watching your mother and father?
  11. What does a day in the life of a married couple in a very healthy relationship look like?
  12. Besides cheating, what can your significant other do so you can end the relationship?
  13. What can a person do besides appearance to instantly become more attractive to you?

Questions about your boyfriend's worldview

  1. What group of people can't you take seriously?
  2. What is the most disturbing thing you have had to accept?
  3. What makes you always cringe?
  4. Something small that makes a big difference?
  5. What is the most annoying thing you face every day?
  6. Who is closest to being a perfect human being?
  7. What makes you feel old?
  8. What is the saddest story in history?
  9. What is considered normal and accepted by society, but really should not be?
  10. What are your personal tips for living a great life?
  11. What is the worst emotion?
  12. What do people most often take for granted?
  13. What quote are you tired of hearing?
  14. What must your child do for you to disown him?
  15. What was the most intriguing internet mystery you've ever come across?
  16. When is the best time to act first and ask for forgiveness later?
  17. What surprises you when so many people say they don't know how to do it?
  18. What was the biggest lie your teachers told you when you were at school?
  19. What have you tried based on the hype around it and didn't live up to your expectations, even if other people are crazy about it?
  20. What would you like to be told about in the past so you don't have to learn from your mistakes?
  21. What is the dumbest thing that many people believe?
  22. When was the last time you felt that your perception of reality had changed significantly?
  23. Who do you know has some belief that is easy to prove false and wrong? What is their belief, and how do they justify it?
  24. If you see money on earth, where is the line between when you take it and when you leave it?
  25. What is the most useful compulsory lesson to be added to public schools?
  26. If you knew you were wanted for a murder you didn't commit, would you turn yourself in?
  27. What was not as bad as you thought, and what, on the contrary, was much worse than you expected?
  28. What hurtful comment your parents left stuck in your head?
  29. What is the biggest waste of money for you?
  30. Is there anything you need advice about?
  31. Whom do you aspire to be more like?
  32. What do you argue about most often?
  33. What do you think will cease to exist in your lifetime?
  34. When was the best time in history to live?
  35. What used to be only for the rich but is now mostly associated with poverty?
  36. What is the most annoying question you get asked regularly?
  37. What do you think is the best period in a person's life?
  38. What do you think has become too socially acceptable?
  39. What is the cutest thing you have seen someone do?
  40. What is worth spending time on?
  41. What behavior makes you think that a person has a lot of followers?
  42. What bad experience should everyone have?
  43. What would you like to stop doing?
  44. What did you reluctantly try once and then become a devoted fan?
  45. What did you boycott about?
  46. What places have become much better or worse because of technological advances?
  47. What industry does not recognize that it is obsolete?
  48. What is the dumbest social issue that people are arguing about?
  49. What social problem deserves more attention?
  50. What is the best way to travel?
  51. What more does the world need?
  52. Do you agree with the statement that happiness lies in ignorance?
  53. Where could you settle?
  54. What makes a person appear ignorant or intelligent?
  55. What's the best advice you've ever been given?
  56. What minor inconvenience bothers you more than it should?
  57. What advice from the future would you give to your present self?
  58. What have you seen on the Internet that still haunts you?
  59. What lie would you never want to know the truth about?
  60. What's the worst text message you ever wake up to?

Fun questions to ask your boyfriend

  1. What movie changed the way you see the world?
  2. What kind of vague entertainment do you like?
  3. What game did you spend the most time on?
  4. What is the most romantic and sweetest movie you still like to watch?
  5. What song can't you listen to?
  6. What movie do you never get tired of watching over and over again?
  7. What can you add to any film to make it better?
  8. What do most movies/series get wrong about?
  9. What was the worst movie ending you've ever seen?
  10. Who would be the best fictional character to be the best friend?
  11. What movie scene traumatized you when you were a child?
  12. What are the positive and negative effects of the growing popularity of social networks?
  13. Which minor character in a work of fiction or play was more interesting than the main character?
  14. What TV show has been running for too long or is still running but should have been canceled a long time ago?
  15. What is your favorite and relatively unknown YouTube channel?
  16. If you had to start a podcast, what would it be about?
  17. Which TV series intro do you never miss?
  18. What's your favorite GIF?
  19. What music videos made a strong impression on you?
  20. What movie have you seen but still don't know what it is about?
  21. What old movie plots today simply fail because of modern technology?
  22. What TV cliché never happens in real life?
  23. Who was the most villainous hero and the most heroic villain?
  24. How do you find new shows/music?
  25. What is the strangest thing you have seen or heard from the media?
  26. What is the best documentary you have seen?

So that's the end of the list, but I have a little bonus for you! Below are some of the things you want to watch out for and these are red flags in a relationship.

📖 We offer you: Funny Questions - Funny Conversations - Interesting Questions

Red flags in a guy

If you notice something from this list in your boyfriend, then this is a big red flag. Don't ignore it. You should seriously consider whether you want to continue the relationship. In fact, I would recommend ending the relationship if you notice any of this. It is better to go through a little pain now than to go through a lot of pain, a painful divorce or breakup later.

Someone or something is always to blame for his failures.

Usually people of this type do not see that they are the cause of their own problems. They don't realize that they could have avoided their troubles by taking some action. They do not realize that they themselves can solve their problems. Because they don't see or feel guilty, they see no reason to improve or change.

He is cruel to animals or people for no reason or just because it's funny.

This probably means that there is cruelty in him. And he will be cruel to you too if he hasn't already started. I have never seen a man become less violent, so don't expect your boyfriend to change. Just leave while you can.

He lies a lot about minor things and won't admit he lied when confronted with evidence.

Lying to avoid trouble is quite common. I am now talking about strange and unfounded lies for no reason. For example, he might tell you about an uncle he doesn't really have, or lie about how he got a certain shirt for no reason.

📖 We offer you: How to start a conversation: 3 important tips

Seriously, just run. I have come across this several times. The little lie is the one you eventually found out about. But there are also big lies, where you have no idea where there is a lie and where is the truth.

Everyone else doesn't see him as the cool guy you see in him.

Yes, you probably can't see the forest for the trees. We've all been there. You are in love, so you turn a blind eye to their shortcomings. But if everyone around you doesn't like your boyfriend and is trying to warn you about him, you should listen.

Sometimes you can be blinded by your short distance with him. Turn on your awareness to look at your boyfriend from the side - as if it were someone else who is watching him and his actions. And don't make excuses for the truth you see.

Questions for the guy you like: more than 50 interesting options


Questions for a guy you like: over 50 interesting options: Pexels

The perfect way to get to know a guy better is to ask thoughtful questions. This will help to demonstrate interest in the interlocutor and fill in awkward pauses. What to ask and what questions you should not ask, experts from Parade and Voice magazines said.

What questions to ask a guy when meeting?

Relationship expert Kelly Gonsalves says it's important to make the person feel special and interesting when meeting someone. To do this, you need to listen carefully to the guy and ask questions based on what you hear. For example, if the interlocutor mentioned that he loves summer, ask why exactly and what he especially likes about this time of year.

If there is an awkward pause and the conversation stalls, try asking the following questions:

  • What 5 films would you recommend me to see?
  • Which country would you like to visit?
  • What makes you feel satisfied?
  • When you're in a bad mood, do you prefer to be left alone or cheered up?
  • What makes you smile even on your worst days?
  • What qualities do you admire in your parents?
  • Do you consider yourself an extrovert or an introvert?
  • What would you like to change about yourself?
  • Do you believe in a second chance?
  • What is your favorite book/movie and why is it so memorable?
  • When did you get your biggest adrenaline rush?
  • What is your ideal vacation?
  • How do you rate your sense of humor? Do people always get your jokes right?
  • What is your favorite song?
  • What did you dream of becoming as a child?
  • Are you now doing what you dreamed about as a child?
  • Where do you like to go most of all - to the movies, restaurants, clubs, or maybe a planetarium?
  • Is there anyone you can talk to about anything?

You can also ask the guy if he likes to travel and is ready to move to another country (city) for love.

What questions to ask a guy when meeting: Pexels

Questions to ask a guy in correspondence

When communicating with a guy on the Internet, it is important to show your interest. To do this, the bestselling author of How to Win Friends and Influence People Dale Carnegie recommends asking the interlocutor about him, his hobbies, interests, plans for the future. For example, ask, “What is on your wish list for this year?”, “Does your job make you happy?” or “What was the best part of your life?”

What can I ask a pen pal? To get to know someone better, Parade magazine experts recommend asking the following questions:

  • How serious are you about online dating?
  • What is the most interesting thing next to you right now? Send me a photo.
  • Is friendship possible between a guy and a girl?
  • How would you describe your best friend?
  • What is the craziest thing you have ever done? Would you do it again?
  • If a genie promised you 3 wishes right now, what would you make?
  • Which parent are you closer to? Why?
  • What do you pay more attention to when communicating - appearance or intelligence?
  • What is your biggest mistake in life? Did she teach you anything?
  • What movie or TV show best describes your week?
  • What is the worst and best thing about being a man?
  • How do you feel about long distance relationships?
  • What is the worst message you accidentally sent to the wrong person?

Since you communicate by correspondence, these questions will be appropriate. They will help maintain communication and, according to the experts of Parade magazine, will bring you closer to the interlocutor.

What to ask a pen pal: Pexels

What to ask a teenage guy?

According to the experts of the portal "Personal self-development", when communicating with a guy, regardless of his age, it is important to learn about his personality, beliefs, likes, dislikes and hobbies. To do this, we recommend asking your teenager the following:

  • What three words describe you?
  • Did you go to concerts? Which one did you visit first?
  • If you could change your name, what would it be?
  • Who was your favorite teacher?
  • What is your favorite subject at school?
  • How do you spend your free time?
  • Do you play computer games? What exactly?
  • Would you risk your life to save someone?
  • If you could win an Olympic medal in any sport, what would it be?
  • Do you like fast food? What exactly?
  • Would you like to become famous someday? What exactly?
  • Would you like to go to a foreign country alone?
  • Who would you save if your house was on fire?
  • What is the strangest gift you have ever received?
  • If you were offered a role in a movie, would you rather play a villain or a hero?
  • How do you see your ideal girlfriend?

You can also ask your teenager questions that will help reveal his personal qualities. For example, are you ready to help a stranger for free.

What to ask a teenage guy: Pexels

What not to ask guys about

When talking with a guy and asking him questions on various topics, it is important not to spoil the impression of yourself and not reduce the conversation to nothing. To do this, do not ask the interlocutor about politics, religion and his ex.

What can't you ask a guy you like? Voice magazine experts believe that men should not be asked provocative questions, for example:

  • Should I cut my hair / change my hair color?
  • Should I wear a dress or a pantsuit?
  • If you could sleep with Monica Bellucci or Angelina Jolie, would you take it?
  • Have you noticed that I have lost/gained weight?
  • Will you come with me to my parents' wedding anniversary?
  • May I have a serious talk with you?

Such questions often become the subject of jokes, and the answers to them provoke quarrels and even partings, because there is no right answer to them.

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