300 questions to ask your boyfriend (2023)

Table of Contents
INDEX The best questions to ask your boyfriend 1. What would be the absolutely perfect day? 2. What did you learn a little late? 3. Why are you so hard on yourself? 4. How often do you feel completely exhausted? 5. If money were not an issue, where would you live? 6. Who was the most toxic person you have ever met? 7. What were the last two books you read? 8. What habits do you have that annoy other people? 9. What makes you nervous? 10. What makes you angry more than you should? 11. What movie was so sad you'll never see it again? 12. What are the two most important lessons you have learned from past relationships? 13. What disgusting and unhealthy things do people do that annoy you? 14. What habit do you have that you think few people have? 15. What do most people overestimate or underestimate about you? 16. What is one thing you probably should do but never do? 17. What was the best thing about how your parents raised you? 18. What do you look forward to the most about growing old? 19. What is the biggest sign of weakness in a person? 20. What did you try very hard to like but couldn't? 21. What makes you different from most people? 22. What was the best mistake you ever made? A mistake that went very well. 23. If you dropped everything and went on a trip, where would you go? 24. What are the most and least masculine things you have done? 25. How do you feel about pets and animals? funny questions to ask your boyfriend Personal questions to ask your boyfriend Questions about your boyfriend's past Questions about the people in your boyfriend's life Relationship questions to ask your boyfriend Questions to ask about your boyfriend's worldview funny questions to ask your boyfriend boyfriend red flags Your failures are always someone/something's fault. Is mean to animals or people for no reason or because it's funny. He lies a lot about petty things and won't admit to lying when faced with evidence. Everyone can't see what you can, can't see how good it is. Questions to ask your boyfriend PDF and image

Here are a bunch of great questions to ask your boyfriend. I hope this gives you both something to talk about while you learn a bit more about him.

This article is also available in Spanish.

Guys can be notoriously closed off when it comes to talking and talking, with a lot of one-word responses. Sometimes it can feel like pulling teeth. Hope these questions help. But you will also have to ask a lot of questions below. Or at least encourage him to give you more detailed answers.

Of course, some guys are more than happy to talk about themselves and just keep babbling and babbling. For these guys, these questions are great for getting the conversation going and getting an idea of ​​what kind of person they really are.

Really every guy is different, so with all these questions to ask your boyfriend, your mileage may vary. Some questions will work great for some boyfriends but won't work for other boyfriends.

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

And if those 300 questions aren't enough, we also havequestions for couplesmiquestions to ask a guy.

INDEX

  • The best questions to ask your boyfriend
  • funny questions to ask your boyfriend
  • Personal questions to ask your boyfriend
  • Questions about your boyfriend's past
  • Questions about the people in your boyfriend's life
  • Relationship questions to ask your boyfriend
  • Questions to ask about your boyfriend's worldview
  • funny questions to ask your boyfriend
  • boyfriend red flags

The best questions to ask your boyfriend

1. What would be the absolutely perfect day?

So this is a good question because every man will have an answer. So it's a perfect conversation starter. And you will learn more about what he likes to do.

If you can get involved in what he likes (and vice versa), you'll find that you'll both have a lot more fun with each other.

2. What did you learn a little late?

This is a roundabout question to find out what some of your regrets are. What would you like to have done or learned? This will give you an idea of ​​where you want to go in the future.

3. Why are you so hard on yourself?

This will let you know what standards it meets. Because if he holds himself to a standard, chances are he expects other people to meet that standard as well.

Also, if you're hard on yourself about a lot of things, it probably means you're more motivated to succeed. If he's not hard on himself at all, it probably means he's super laid back or doesn't really want to improve.

4. How often do you feel completely exhausted?

This question is a good indicator of how stressed you are. You can ask what wears him out and find out what he emphasizes the most.

5. If money were not an issue, where would you live?

A great question to find out to what extent the two are compatible. If you both want to live in similar places, that's definitely a good sign. But if he wants to live in the country in a cold place and you want to live in a city in a warm place, well, that doesn't bode well. It's good to know if you plan to be together for the long term.

6. Who was the most toxic person you have ever met?

We all know people who make the world around them a worse place. You can see what your boyfriend considers to be the worst of the worst in people.

Maybe they both despise the same aspect in a person or maybe not. Either way, you will learn what kind of behavior you despise.

7. What were the last two books you read?

Is your boyfriend a reader? Find out with this question. If you're a voracious reader and he's not (or vice versa), this could be a problem. But if you both read the same amount, there's probably nothing to worry about.

And who knows, you might even learn about a cool new book that you can check out.

8. What habits do you have that annoy other people?

Yes, annoying habits. You'll want to know this about him. Because if the two of you live together, those pesky habits will go from cute to frustrating pretty quickly. We all have annoying habits, so feel free to share some of your own and let them know.

9. What makes you nervous?

Being nervous is a universal human trait. So why not find out what makes your boyfriend uncomfortable? Speaking in front of a large group of people is likely to make him nervous, but if you can, push him for more examples.

10. What makes you angry more than you should?

This is a really important question. Because you'll want to know what makes them angry so you can avoid them. And if you can't help but piss them off, you might want to find a new boyfriend. This applies to you too, if you get really mad at them, you may want to reconsider your relationship. Too much anger is toxic in relationships.

11. What movie was so sad you'll never see it again?

This is a great question to find out a little more about your emotional side. You can see what really suffocates them. Or you can see if they really aren't that emotional.

It's good to know anyway because if they never choke during a movie, don't expect them to be open about their own emotions in the future.

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

So don't be jealous of this one. Yes, he has had partners in the past. And these relationships are worth listening to because you can find out a lot.

You can find out a lot about what he expects of you in your past relationships. You can also find out what to expect from him and how he acts when things go wrong.

13. What disgusting and unhealthy things do people do that annoy you?

So how clean and hygienic is your boyfriend? If you're ultimately going to take your relationship to the next level, it's a good thing you find out sooner rather than later.

Basically, if you have a long list of gross things, that probably means you're pretty clean. If he just shrugs and says "I don't know," it probably means he's really dirty.

14. What habit do you have that you think few people have?

We all have strange habits, it's time to discover some of them! Just remember to try not to be too critical. You probably also have your share of strange habits.

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

This question is less about how other people see your boyfriend and more about how they see themselves. You can find out how your boyfriend thinks the world sees him and how that contrasts with how he sees himself.

If he seems a bit delusional, that's a bad sign. If he seems humble, that's probably a good sign.

16. What is one thing you probably should do but never do?

This is a bit of a strange question that can give you a variety of answers. Great for starting an interesting conversation, because you've probably never been asked that before. But whatever your answer is, it will probably be very interesting and enlightening.

17. What was the best thing about how your parents raised you?

Ah, family, sometimes it's a touchy subject, but you can learn a lot about someone by finding out about their childhood.

Just remember to let him talk, don't make assumptions, and never be negative about the family. People get defensive quickly if you talk bad about their family.

18. What do you look forward to the most about growing old?

300 questions to ask your boyfriend (1)

It's fun to ask your boyfriend this question because you'll either get a funny answer or a serious answer about how he wants to live after he retires. Either way, it's a great question to ask.

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

This is a really interesting question to ask. Your answer will say a lot about how you view the world around you.

Basically, whatever the sign of weakness is, that is why you will judge people more harshly. And the opposite of that sign of weakness will be something you really admire and strive to be.

20. What did you try very hard to like but couldn't?

By seeing who pushed him to try to like the thing, you can see who he's trying to please. And you can also see how willing he is to take on that person or group. Also, he will learn more about his likes and dislikes.

21. What makes you different from most people?

A great question to ask your boyfriend that will show how much he feels he fits in with society. If they mention a lot of things, they probably consider themselves outcasts. If they don't have much to say, they probably think they fit in very well with society. There's nothing wrong with either one, but it's good to know.

22. What was the best mistake you ever made? A mistake that went very well.

This probably doesn't tell you much about your boyfriend, but it's a fun question to ask. You will probably hear an interesting story. And who doesn't like a good story?

23. If you dropped everything and went on a trip, where would you go?

This is similar to the previous question "Where would you live?". But instead of finding out where her boyfriend wants to settle, you can find out what kind of vacation her boyfriend likes.

If you both like the same things, it's always better. It means more things to do together and more things to talk about.

24. What are the most and least masculine things you have done?

This is a fun question that can lead to great answers. You can also find out how seriously they take themasculinity conceptand what that concept means to them.

25. How do you feel about pets and animals?

This is a good question to ask for the simple reason that if one of you hates animals and the other loves them, that means one of you is likely to be upset if the two of you live together. It's good general information to collect and can lead to a good conversation.

funny questions to ask your boyfriend

  • How often is your brain on autopilot?
  • What do you think aliens would really look like?
  • What website doesn't exist but should?
  • What inedible thing would you like to eat?
  • What is the craziest place you have danced in?
  • Should the TP be above or below?
  • What's the spiciest thing you've ever eaten?
  • What nonsense are you so proud of?
  • What unnecessary products or services do you consider necessary?
  • What's the best conspiracy theory you can think of on the spot?
  • If jobs/careers had slogans, what would some of their slogans be?
  • What do people really need to relax?
  • What's the most disgusting thing you've ever drunk?
  • Which hairstyles suit which personalities?
  • What scrambles your brain every time you think about it?
  • If colors had flavor, what would each color taste like?
  • What fictional villain made you truly hate them?
  • What is the best stress relief you can get/do for less than $20?
  • How often do you walk into a room and forget why you entered the room?
  • If when you died, you were placed in a room for eternity with people who died the same way, how would you want to die?
  • What would an amusement park full of your biggest fears be like? What tours would you have?
  • What would an amusement park specifically designed to make you happy look like?
  • What do you wish you had never learned how it was made or how it works?
  • What names have ruined you because you met someone terrible with that name?
  • If you could have a remote that would control any type of machine, what would you have a remote for?
  • What do you do in a way, even if it's incredibly inefficient or pointless, because that's how you've always done it?
  • What's the coolest thing scientists can discover while cruising the ocean?
  • What is the funniest/weirdest thing someone has confessed to you while drunk?
  • If someone let you put whatever you wanted on a billboard downtown, what would you put on the billboard?
  • If you had complete genetic control over plants, what would be the coolest tree you could make?
  • Which condiments do you refrigerate and which ones do you leave in the cupboard/pantry?
  • What are some non-traditional ice cream toppings that you think would be awesome?
  • What is the correct amount of ice cream to put in an ice cream cone?
  • If animals were as intelligent as humans, what kinds of jobs would certain animals be uniquely qualified for?
  • Do fish have necks?
  • What's the best "who would win in a fight A or B" you can think of?
  • If you could talk to everyone in your country at once, what phrase would you say that would make most people instantly hate you?
  • If you were forced to participate in a dance competition, what song would you choose to dance to?
  • You have unlimited wishes, but every time you make a wish, the thing you love the most is erased from the world. How many wishes do you ask for and what do you want? (No, you can't wish things weren't erased from the world.)
  • What crazy things will you do if you get rich?
  • How would the world change if there were health potions?
  • What was the last thing you googled?
  • What is a silly joke that you use regularly?
  • What's the weirdest bad text or phone call you've ever received?
  • If you were given immortality but there was a condition, what would prevent you from accepting immortality?
  • If you could change your first name, what would be the most epic name you could choose?
  • Why do you think we dream?
  • If you could change your gender for a period of time of your choosing, would you do it? And if so, how long?
  • What past event would you like to see a recording of?
  • What great idea would you like to try if you had enough money?
  • If you started a cult, what kind of cult would you start?
  • What are you a non-military veteran of?
  • What task are you most afraid of?
  • If wars were abolished, what would be the most interesting way for countries to settle their differences?
  • What is legal but still seems illegal?
  • What rarely works as it should?
  • What should be the next breakthrough in footwear?
  • What product surprises you that no one has made a better version?
  • If you could make a candle with any scent, what type of scented candle would you make?
  • If you could curse your worst enemy so that an everyday household item would let out a blood-curdling scream at random intervals, which item would you curse? (The curse would carry over to a new version of that item if they bought a replacement.)
  • What would you do first if you got the ability to fly?
  • Where and when did you let go of your most inappropriate fart?
  • What era of the imagined future would you like to live in? (i.e. lots of 1950s curvy, chrome and all shiny)
  • What would change if it was socially acceptable to speak openly and frankly about anything?
  • What is the coolest flag in use?
  • What band would be the best to see live if the band name literally described it? (ie Guns and Roses would literally be roses and guns on stage).
  • If you had a secret lair like Batman or Superman, what would it be like?
  • What do you like the least about the activity you like the most?
  • If you were an action figure, what would you come up with and what would your catchphrases be?
  • How well do you think you would do if you got lost in the woods for two weeks?
  • What shortcut would you like to take?
  • What is your favorite time waster?
  • What is the car of your dreams?

More fun questions: You can also try ourfunny questions to ask a guypage or ourfunny questionspage.

Personal questions to ask your boyfriend

  • What do you fear of the future?
  • what scares you the most?
  • What is the worst dream you have ever had?
  • Why do you get too excited?
  • What is the fastest way to make him angry?
  • What event made you mature the most as a person?
  • What's on your wish list?
  • What is the hardest truth you have come across?
  • How would you like your funeral to be?
  • What makes you happier?
  • What would your own personal hell look like?
  • How smooth are you?
  • What mundane task have you mastered?
  • What scary or weird thing do you do regularly?
  • What are the peculiarities of your body?
  • What brutally honest truth about yourself can you share with me?
  • How many of the bad things that happen to you are your fault?
  • What is it like to be you?
  • When did you really try, I mean really try, and it still wasn't enough?
  • When are you more yourself?
  • If your life were a book, what would this chapter be called?
  • What are some incredibly common experiences you've been missing?
  • What steps would you have to take to fulfill a dream that you have had for a long time?
  • What are you a snob about?
  • What would you like to write on your tombstone?
  • What would it be like if you lived up to your potential?
  • How curious are you?
  • How lucky are you?
  • What's your jam?
  • How do you combat procrastination?
  • What weird thing fascinates you?
  • What would you change about your appearance if you had the opportunity?
  • How easily do you change your mind?
  • How affectionate are you?
  • What's the loneliest time you've ever been?
  • What makes you feel alive?
  • How well do you think you can read the emotions of others?
  • What makes you interesting?
  • Who makes you feel uncomfortable when you are around them?
  • In what situations do you act least like yourself?
  • What do you value most?
  • What sounds fill you with dread?
  • What word describes you better than any other word?
  • How neurotic do you think you are?
  • What are you really obsessed with?
  • Who or what is holding you back?
  • How often do you argue with people on the Internet?
  • How adventurous are you?
  • What do you want to get out of life?

More personal questions: take a look at ourpersonal questions to ask a guyor thesepersonal issues.

Questions about your boyfriend's past

  • What were the turning points in your life?
  • What is the most hurtful text you have ever received or sent?
  • What event from your past has come back to haunt you?
  • What are some things you hid from your parents?
  • What was the most embarrassing moment you had at school?
  • What was the smartest thing you did as a child?
  • What unique games or activities did you play as a child?
  • What's the weirdest thing you've seen happen at a job you've ever had?
  • What was your worst injury as a child?
  • What is the most famous thing you have been?
  • What did you steal?
  • What's the coldest thing you've been through?
  • If you could go back and change just one decision you made, what decision would you change?
  • When was the moment you threw caution to the wind and just did it?
  • If your entire life was recorded, but you could choose just one hour of footage to watch, what scenes would you go back and watch?
  • What is the most memorable phone call you have received or made?
  • Where are some places you've been that you can never go back?
  • What movie title best describes your life so far?
  • What changed you for the better and something that changed for the worse?
  • Who did you deliberately cut out of your life?
  • What have you done in the past that people keep bringing up over and over and over again?
  • Who is the nicest person you have ever met?
  • What is the most interesting abandoned place you have been to?
  • What were some of your favorite childhood books?
  • What is your most beautiful memory?
  • What did you do when you were younger that you still shudder when you think about it?
  • How much have you changed in 5 years?
  • What do you wish you had/hadn't said?
  • What story involving you is probably told by the most people?
  • What is your worst vomiting story?
  • What's the most American thing you've ever done? (Regardless of being American or not).
  • What's the riskiest thing you've ever done?
  • When was the last time you were very, very wrong about something?
  • What bridges have you burned?
  • What's the most awkward thing you've ever had to say to someone?
  • What is the most memorable vacation you've ever taken?

We also have a talking points page that hasa section on personal history.

Questions about the people in your boyfriend's life

  • How well do your family members get along?
  • Who in your life has the most positive outlook on life?
  • What was your closest friendship that fell apart?
  • What stupid things have you convinced your friends to do?
  • What's the weirdest thing someone has said to you?
  • Who in your life is most likely to be a serial killer?
  • What happened to your best friend from high school?
  • How often do you talk to your extended family?
  • What are some scandals that happened in your circle of friends?
  • Who is the black sheep in your family?
  • Who is the most difficult person you have to deal with on a regular basis?
  • What are the three most important things you learned from your parents?
  • Who do you know who is full of unfounded confidence about their opinions?
  • What secret is someone hiding from you, but you already know everything about them?
  • What new plausible rumor can you come up with about a celebrity or a friend in your circle of friends?
  • When was the moment you thought you knew someone, but it turned out to be a totally different person?

Relationship questions to ask your boyfriend

  • What is the best marriage or relationship advice you have received?
  • What is your number one rule in a relationship?
  • What is the role of a wife?
  • Where do you get your ideas about what a good relationship is?
  • What are the best and worst things about being in a long-term relationship?
  • Who in your life has the healthiest relationship with your SO?
  • What isthe best dateWe have been?
  • What do you think is the best and worst thing about having you as SO?
  • How much work should a couple put in to have a strong relationship?
  • How serious should it be before a couple sees a marriage counselor?
  • What did you learn about relationships by watching your mom and dad?
  • What is a day in the life of a couple in a super healthy relationship like?
  • Besides cheating, what can an SO do to end a relationship?
  • What is something (besides appearance) that a person can do to instantly become more attractive to you?

Questions to ask about your boyfriend's worldview

  • What group of people do you find impossible to take seriously?
  • What is the most disturbing thing you have come to terms with?
  • What can someone say that always makes you cringe?
  • What is something small that makes a big difference?
  • Who is closest to being a perfect human being?
  • What makes you feel old?
  • What is the saddest story you know of history?
  • What is considered normal and accepted but really shouldn't be?
  • What are some of your personal tips on how to live an extraordinary life?
  • What is the worst emotion?
  • What is it that people often take for granted?
  • What quote are you tired of hearing?
  • What would your son have to do for you to reject him?
  • What's the most intriguing internet mystery you've come across?
  • When is it better to act first and apologize later?
  • What surprises you that many people don't know how to do?
  • What was the biggest lie your teachers told you when you were in school?
  • What have you tried that doesn't live up to expectations, even though other people seem to be crazy about it for some reason?
  • What do you wish someone had told you so you didn't have to learn the hard way?
  • What is the dumbest thing that many people believe?
  • When was the last time you felt your perception of reality changed significantly?
  • Who around you has a belief that you cling to, even if it is easily proven wrong? What is their belief and how do they rationalize it?
  • If you see money on the floor, where is the line between picking it up and not picking it up?
  • What would be the most useful required class to add to public schools?
  • If you found out you were wanted for a murder you didn't commit, would you turn yourself in?
  • What wasn't as bad as you thought it would be, and what was much worse than you expected?
  • What off-the-cuff comment one of your parents made has stuck with you over the years?
  • What is the biggest waste of money?
  • What do you need advice on?
  • Who do you aspire to be more like?
  • What do you find yourself arguing about most often?
  • What do you think will cease to exist during your lifetime?
  • When in history was the best time to be alive?
  • What used to be only for the rich but is now more associated with poverty?
  • What is the most annoying question you receive on a regular basis?
  • What do you think is the best period of a person's life?
  • What do you think became very socially acceptable?
  • What's the meanest thing you've ever seen someone do?
  • What behavior makes you think someone has a lot of class?
  • What bad experience should everyone have to go through?
  • What do you wish you could stop doing?
  • What did you reluctantly try once and then become a die-hard fan?
  • Where are some places that have gotten much better or worse due to technological advances?
  • What sector denies being obsolete?
  • What social problem deserves more attention?
  • What is the best way to travel?
  • Is ignorance bliss?
  • What would be your perfect place to settle?
  • What makes a person appear ignorant or intelligent?
  • What is the best advice you have received?
  • What little inconvenience bothers you a lot more than it should?
  • What advice do you think you would give for the future?
  • What did you see online that still haunts you?
  • What lie do you wish you had never discovered the truth?
  • What would be the worst text to wake up and see?

funny questions to ask your boyfriend

  • What movie changed the way you see the world?
  • What is the darkest entertainment that you really enjoy?
  • What game have you spent more hours on?
  • What's the cheesiest movie you still love to watch?
  • What's the song you can't stand listening to?
  • What movie do you always want to see again?
  • What can you add to any movie to make it better?
  • What do most movies/TV shows get wrong?
  • What's the worst movie ending you've ever seen?
  • Who would be the best fictional character to have as a best friend?
  • What movie scene traumatized you as a child?
  • What are the best and worst effects of popularity on social media?
  • What supporting character in a work of fiction or play was more interesting than the main character?
  • What TV show ran a long time or is it still on and should have been canceled long ago?
  • What is your favorite relatively unknown YouTube channel?
  • If you had to start a podcast, what would your podcast be about?
  • What intro show do you always watch until the end?
  • What is your favorite gif?
  • Which music videos made a strong impression on you?
  • What movie have you seen but still don't know what it's about?
  • What old movie plots just wouldn't work today because of modern technology?
  • Who was the most villainous hero and the most heroic villain?
  • How do you find new shows/music?
  • What's the weirdest medium you've ever seen or heard?
  • What is the best documentary you have seen?

That's the end of the list of questions, but I have a little bonus for you! Below are some things to watch out for, relationship red flags.

boyfriend red flags

If you notice any of these on your boyfriend, that's a huge red flag. Do not ignore it. She should seriously consider whether she wants to continue the relationship. In fact, she would only recommend stopping if she notices any of these. Better a little pain now than a lot of pain later and a complicated divorce/separation.

Your failures are always someone/something's fault.

Usually, this type of person does not realize that he is the cause of his own problems, that he could have prevented his problems by taking action, or that he can actually solve his problems. Since they are not guilty of anything, they see no reason to improve or change.

Is mean to animals or people for no reason or because it's funny.

This probably means that they have a cruel and serious streak. And they will also be cruel to you if they haven't started yet. I've never seen a person become less cruel, so don't expect your boyfriend to. Just leave now while you still have a chance.

He lies a lot about petty things and won't admit to lying when faced with evidence.

These are not normal lies to avoid trouble, this is quite common. I'm talking about weird lies for no reason. Like telling you about a guy they don't really have or lying about how they got a certain shirt for no reason.

Seriously, just run. I have come across this several times. The little lies are the ones you discover. There are bigger lies. And you have no idea what is a lie and what is true.

Everyone can't see what you can, can't see how good it is.

Yeah, you probably can't see the forest because of the trees. We have all been there. You're in love, so you cover up their flaws. But if everyone around you doesn't like your boyfriend or is trying to warn you about him, you might want to listen to them.

Sometimes being too close can blind you. Make a conscious effort to look at your boyfriend from a distance as if you were someone else looking at him and observing how he acts. And don't make excuses for any truth you see.

Questions to ask your boyfriend PDF and image

here is onePDF of all our questions to ask your boyfriend. Cherish!

and here it isa picture of all the questions to ask your boyfriendif you prefer it over a PDF.

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