Questions To Ask Your Boyfriend

Here is a load of great questions to ask your boyfriend. Hopefully these will give you both something to talk about while learning a little more about him.

Guys can be notoriously closed off when it comes to talking and conversation, with lots of one word answers. Sometimes it might feel like pulling teeth. Hopefully these questions will help. But you’ll need to ask a lot of follow questions as well. Or at least encourage him to give you more detailed answers.

Of course some guys are more than happy to talk about themselves and will chatter on and on. For these guys, these questions are great for steering the conversation and getting some insight on what kind of person they really are.

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

To help you out I’ve put the best questions first with some commentary. Then I’ve got some extra questions to ask your boyfriend at the end of the article in different categories (fun, personal, his past, the people in his life, relationship questions, worldview, entertainment). Also at the bottom of the page is a PDF and image of all the questions. And finally to top it all off I’ve got some boyfriend red flags you’ll want to watch out for.

You’ll 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 that out of the way, let’s get started!

Question 1: What movie was so sad that you will never watch it again?

This is a great question for finding out a little more about their emotional side. You can see what really chokes them up. Or you can see if they really aren’t that emotional.

Good to know either way, because if they never get choked up during a movie, don’t expect them to be open about their own emotions in the future.

Question 2: What are the two biggest lessons you’ve learned from previous relationships?

So don’t get jealous on this one. Yes, he has had partners in the past. And it’s worth hearing about those relationships because you can find out a lot.

You can find out a lot about what he’ll expect from you from his previous relationships. You can also find out what to expect from him and how he acts when things go bad.

Question 3: What would be the absolute perfect day?

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

If you can get into stuff that he likes (and vice versa), you’ll find that you will both have a lot more fun around each other.

Question 4: What did you learn a little too late?

This is a roundabout question to find out what some of his regrets are. What does he wish he had done or learned? It’ll give you an idea of where he wants to head in the future.

Question 5: What gross and unhygienic things do people do that bothers you?

So, how clean and hygienic is your boyfriend? If you are going to take your relationship to the next level eventually, it’s good to find out sooner rather than later.

Basically if he has a long list of gross things that probably means he’s pretty clean. If he just shrugs and says “I dunno”, it probably means he’s pretty dirty.

Question 6: What habit do you have that you think not many other people have?

We all have weird habits, time to find out some of his! Just remember to try not to be too judgmental. You’ve probably got your share of weird habits as well.

Question 7: What are you too hard on yourself for?

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

Also, if he is hard on himself about a lot of things, it probably means he is more driven to succeed. If he isn’t hard on himself about anything, it probably means he is super laid back or he doesn’t really want to improve himself.

Question 8: What habits do you have that annoy other people?

Yeah, annoying habits. You’ll want to know these about him. Because if you two ever move in together, those annoying habits will go from cute to frustrating real quick. We all have annoying habits, so feel free to share some of yours and give him a heads up.

Question 9: What do most people overestimate or underestimate about you?

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

If he sounds a little delusional, that’s a bad sign. If he sounds humble, it’s probably a good sign.

Question 10: How often do you feel utterly worn down?

This question is a good indicator of how stressed he is. You can ask what wears him down and find out what he stresses about most.

Question 11: What is something you probably should do, but will never do?

This is a bit of a weird question that can get you a variety of answers. Great for an interesting conversation starter because he has probably never been asked this. But whatever his answer is, it’ll probably be pretty interesting and enlightening.

Question 12: What was the best thing about how your parents raised you?

Ah family, sometimes a touchy topic but you can learn a lot about someone by finding out about their childhood.

Just remember to let him do the talking, don’t make assumptions, and never be negative about family. People get defensive real quick if you talk bad about their family.

Question 13: What do you most look forward to about getting old?

This question is a fun one to ask your boyfriend because you’ll either get funny answer or a serious answer about how he wants to live after he retires. Either way it’s a great question to ask.

Question 14: What is the biggest sign of weakness in a person?

This is a really interesting question to ask. Their answer will tell you a lot about how they see the world around them.

Basically whatever the sign of weakness is, that will be what he judges people most harshly for. And the opposite of that sign of weakness will be something he really admires and strives to be.

Question 15: What’s something you tried really hard to like but just couldn’t?

By seeing who pressured him into trying to like the thing, you can see who he tries to please. And you can also see how much he is willing to stand up to that person or group. Plus, you’ll learn more about what he likes and doesn’t like.

Question 16: What makes you different from most people?

A great question to ask your boyfriend that will show you how much they feel like they fit into society. If they mention a lot of things, they probably see themselves as an outcast. If they don’t have much to say, they probably think they fit pretty well into society. There’s nothing wrong with either one, but it’s good to know.

Question 17: What was the best mistake you’ve made? A mistake that turned out really well.

This one probably won’t tell you much about your boyfriend but it’s a fun question to ask. You’ll probably get to hear an interesting story. And who doesn’t love a good story?

Question 18: If money was no object, where would you live?

A great question for finding out how much you two match up. If you both want to live in similar places, that’s definitely a good sign. But if he wants to live out 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 something good to know if you plan on being together long term.

Question 19: Who was the most toxic person you’ve known?

We’ve all known people that 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 you both despise the same aspect in a person or maybe not. Either way, you’ll learn what types of behavior he despises.

Question 20: What were the last two books that you read?

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

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

Question 21: If you dropped everything and went on a road trip, where would you go?

This one is similar to the “where would you live” question above. But instead of finding out where your boyfriend wants to settle down, you can find out what type of vacation your boyfriend likes.

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

Question 22: What makes you nervous?

Getting nervous is a universal human trait. So why not find out what makes your boyfriend uncomfortable? There’s a good chance that one thing that makes him nervous is talking in front of a large group of people, but press him for more examples if you can.

Question 23: What makes you angrier than it should?

This is a really important question. Because you’ll want to know what makes them angry so you can avoid it. And if you can’t avoid making them angry, you might want to find a new boyfriend. This goes for you too, if you find yourself getting angry at them a lot, chances are that you might want to reconsider your relationship. Too much anger is toxic in relationships.

Question 24: What are the manliest and least manly things you have ever done?

This is a fun question that can lead to some great answers. You can also find out how seriously they take the concept of manliness and what that concept means to them.

Question 25: How do you feel about pets and animals?

This one is good to ask for the simple reason that if one of you hates animals and one of you loves them, that means that one of you is probably going to be upset if you two move in together. It’s some good general info to gather and can lead to a good conversation.

Extra questions to ask your boyfriend

Here are some more questions to ask your boyfriend that I think you’ll enjoy. No commentary on these. I just wanted to give you some more options if the questions above weren’t enough for you.

Fun questions to ask your boyfriend

What’s the funniest / strangest thing that someone has drunkenly confessed to you?
How often is your brain on autopilot?
How often do you go into a room and forget why you went into the room?
What is the strongest animal you could win against with just your bare hands and feet?
Which fictional villain made you feel real hatred towards them?
If when you died, you got put into a room for eternity with people who died the same way, how would you want to die?
What would an amusement park filled with your biggest fears be like? What rides would it have?
What would an amusement park designed specifically to make you happy, be like?
What’s something you wish you had never learned how it was made or how it works?
What names were ruined for you because you knew someone terrible with that name?
If you could have a remote control that controls any one type of machine, what would you have a remote for?
What’s something you do one way even though it’s incredibly inefficient or nonsensical because that’s how you’ve always done it?
What’s the coolest thing scientists could uncover while searching the ocean?
What do you think aliens would actually look/be like?
What website doesn’t exist but should?
If jobs/careers had slogans what would be some of their slogans?
What’s the most stress relieving thing you can get/do for less than 20$?
What do people really need to chill out about?
What’s the grossest thing you’ve drunk?
If someone let you put whatever you wanted on a billboard in the center of your town or city, what would you put on the billboard?
Which hairstyles fit with which personalities?
What scrambles your brain every time you think about it?
If colors had a taste, what would each color taste like?
If you had complete genetic control over plants, what is the coolest looking tree you could make?
What inedible thing do you wish you could eat?
What condiments do you refrigerate and which do you leave in the cabinet/pantry?
What’s the spiciest thing you’ve eaten?
What unnecessary products or services do you consider necessary?
Where is the craziest place you have danced?
What are some non-traditional toppings for ice cream that you think would be pretty awesome?
What silly thing do you take a lot of pride in?
What’s the best conspiracy theory you can make up on the spot?
How much is the correct amount of ice cream to put on an ice cream cone?
Should TP hang over or under?
If animals were as intelligent as humans, what types 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 come up with?
If you could speak to everyone in your country at the same time, what sentence could you say that would make the most amount of people instantly hate you?
If you were forced into a dance competition, what song would you choose to dance to?
You have unlimited wishes but every time you make a wish what you love most is erased from the world. How many wishes do you make and what do you wish for? (No, you can’t wish not to have things erased from the world.)
What crazy things will you do if you ever become rich?
How would the world change if health potions existed?
What’s the last thing you Googled?
What’s a lame joke you use on a regular basis?
What’s the weirdest wrong number text or phone call you’ve gotten?
If you were given immortality, but there was one condition, what would stop 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 switch genders for a length of time of your choosing, would you? And if so, how long?
What event from the past do you most want to see a recording of?
What great idea would you like to try if you had enough money?
If you were in a high-speed chase, what song would you want blaring on the radio?
If you started a cult, what kind of cult would you start?
What are you a non-military veteran of?
What chore do you dread most?
If wars were abolished, what would be the most interesting way for countries to settle their differences?
What’s legal but still feels illegal?
What seldom works the way it should?
What should be the next advancement in shoes?
What product are you shocked that no one has made a better version of?
If you could make a candle with any scent, what type of scented candle would you make?
If you could place a curse on your worst enemy so that one everyday household item would at random intervals let out a blood-curdling scream, what item of theirs would you curse? (The curse would transfer to a new version of that item if they bought a replacement.)
What would you do first if you gained the ability to fly?
Where and when did you let out your most inappropriate fart?
What era’s imagined future would you most want to live in? (i.e. 1950’s lots of curves, chrome, and everything 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 coolest to see live if their band name literally described the band? (i.e. 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 love least about the activity you love most?
If you were an action figure, what would you come with and what would your catch phrases be?
If could be the first person to do something, what would your achievement be?
How well do you think you would do if you were lost in the woods for two weeks?
What shortcut do you wish you could take?
What’s your favorite waste of time?
What’s your dream car?
Personal questions to ask your boyfriend

What brutally honest truth about yourself can you share with me?
What about you scares you the most?
How much of the bad stuff that happens to you is your fault?
What’s it like to be you?
When did you really try hard, I mean really whole assed it, and it still wasn’t enough?
When are you the most yourself?
If your life was a book, what would this chapter be called?
What do you fear about the future?
What mundane task have you mastered?
What creepy or cringey thing do you do on a regular basis?
What are some incredibly common experiences that you’ve missed out on?
What’s the worst dream you’ve ever had?
What do you get overly emotional about?
What’s the quickest way to make you angry?
What event made you mature as a person the most?
What’s on your bucket list?
What’s the hardest truth you’ve come to grips with?
What would you want your funeral to be like?
What would your very own personal hell be like?
How soft are you?
What quirks does your body have?
What steps would you have to take to achieve a dream you’ve had for a long time?
What are you a snob about?
What makes you the happiest?
What do you want to be written on your tombstone?
What would it look like if you fully lived up to your potential?
How curious are you?
How lucky are you?
What’s your jam?
How do you fight off procrastination?
What odd thing are you fascinated by?
What about your appearance would you change if you had the chance?
How easily do you change your opinions?
How nurturing are you?
What is the most alone you’ve ever been?
What makes you feel alive?
How well do you think you can read others’ emotions?
What makes you interesting?
Who makes you uncomfortable when you are around them?
In what situations do you act least like yourself?
What do you value most?
What sounds fills you with dread?
What word describes you better than any other word?
How neurotic do you think you are?
What are you really obsessed about?
Who or what is holding you back?
How often do you get into arguments with people on the internet?
How adventurous are you?
What do you want to get out of life?
Questions about your boyfriend’s past

What were the turning points of your life?
What’s the most painful text you’ve ever received or sent?
What event in your past has come back to haunt you?
What are some things you hid from your parents?
If you could go back and change just one decision you made, what decision would you change?
What was the most awkward moment you had at school?
What was the cleverest thing you did as a child?
What unique games or activities did you play as a child?
What’s the strangest thing you’ve seen happen at a job you’ve had?
What was your worst injury as a child?
What’s the most famous you’ve been?
If your whole life was recorded, but you could only choose an hour of footage to watch, what scenes would you go back and watch?
What have you stolen?
What’s the coldest you’ve ever been?
When was a time you threw caution to the wind and just went for it?
What’s the most memorable call you’ve taken or made?
Where are some places that you’ve been that you’ll never be able to go back to?
What movie title best describes your life so far?
What’s something that has changed you for the better and something that has changed you for the worse?
Who have you purposely cut out of your life?
What did you do in the past that people keep bringing up over and over and over again?
Who is the nicest person you’ve ever met?
Where is the most interesting abandoned place you’ve 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 cringe 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 has probably been told by the most people?
What’s your worst vomiting story?
What’s the most American thing you’ve ever done? (Regardless of whether are American or not.)
What’s the riskiest thing you’ve ever done?
When was the last time you were really, really wrong about something?
What bridges have you burned?
What’s the most uncomfortable thing you’ve had to tell someone?
What’s the most memorable vacation you’ve taken?
Questions about the people in your boyfriend’s life

How well do your family members get along?
What are some scandals that happened in your circle of friends?
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 friends to do?
What plausible new rumor can you come up with on the spot about a celebrity or friend in your circle of friends?
What’s the most awkward thing someone has said to you?
What happened to your best friend from elementary school?
How often do you talk to your extended family?
Who do you know is full of unfounded confidence about their opinions?
Who’s the black sheep in your family?
What are the three most important things you learned from your parents?
What secret is someone keeping from you, but you already know all about it?
When was a time that you thought you knew someone, but they turned out to be an entirely different person?
Who in your life is most likely to be a serial killer?
Who’s the most difficult person you must deal with on a regular basis?
Relationship questions to ask your boyfriend

What does a day in the life of a couple with a super healthy relationship look like?
What’s the best marriage or relationship advice you’ve gotten?
What’s your number one rule in a relationship?
What do you think is the best and worst thing about having you as an SO?
Besides cheating, what can an SO do that would make you end a relationship?
What is something (beside appearance) that a person can do to become instantly more attractive to you?
What is the role of a wife?
What’s the best and worst things about being in a long-term relationship?
What did you learn about relationships from watching your mother and father?
Who in your life has the healthiest relationship with their SO?
How serious should it get before a married couple goes to a marriage counselor?
Where do you get your ideas about what a good relationship is?
How much work should a couple put into having a strong relationship?
Questions to ask about your boyfriend’s worldview

What group of people do you find it impossible to take seriously?
What’s the most disturbing thing you’ve come to accept?
When was the last time you felt your perception of reality shift in a major way?
Who around you has a belief that they hold onto, even though it’s easily proven to be wrong? What’s their belief and how do they rationalize it?
What can someone say that always makes you cringe?
When is it better to act first and ask for forgiveness later?
What are you surprised a lot of people don’t know how to do?
If you see money on the ground, where is the line between you picking it up and you not picking it up?
What’s something small that makes a big difference?
What do you wish someone had told you, so you didn’t have to learn the hard way?
What’s the most frustrating thing you encounter daily?
Who is the closest to being a perfect human?
What was the biggest lie your teachers told you when you were in school?
What is something you tried that doesn’t live up to the hype even though other people seem to be crazy about it for some reason?
What is the dumbest thing that a lot of people believe?
What would be the most useful mandatory 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 makes you feel old?
What is the saddest story you know from history?
What is considered normal and is accepted but really shouldn’t be?
What are some of your personal tips on how to live a remarkable life?
What is the worst emotion?
What do people most often take for granted?
What quote are you sick and tired of hearing?
What would your child have to do for you to disown them?
What was the most intriguing internet mystery you’ve come across?
What’s something that wasn’t as bad as you thought it would be and what is something that was way worse than you expected it to be?
What off-handed comment a parent made has stuck with you through the years?
What’s the biggest waste of money?
What do you need advice about?
Who do you aspire to be more like?
What do you find yourself getting into arguments 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 now is mostly associated with poverty?
What’s the most annoying question you get asked on a regular basis?
What do you think is the best period of a person’s life?
What do you think has gotten too socially acceptable?
What’s the pettiest thing you’ve seen someone do?
What’s the most worthwhile thing a person can spend their time on?
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 one time and then became a diehard fan of?
What have you boycotted?
Where are some places that got much better or much worse due to technological advances?
What industry is in denial about being obsolete?
What’s the silliest social issue people get up in arms about?
What social issue deserves more attention?
What’s the best way to travel?
What does the world need more of?
Is ignorance bliss?
Where would your perfect place to settle down be?
What makes a person seem ignorant or intelligent?
What’s the best advice you’ve ever been given?
What minor inconvenience bothers you way more than it should?
What advice do you think future you would give current you?
What did you see online that still haunts you?
What lie do you wish you never learned the truth of?
What would be the worst text to wake up and see?
Entertainment questions to ask your boyfriend

What movie changed how you looked at the world?
What scene from a movie traumatized you when you were a child?
What are the best and worst effects of social media becoming popular?
What is the most obscure entertainment you really enjoy?
Which side character in a piece of fiction or game was more interesting than the main character?
What game have you put the most hours into?
What is the cheesiest movie that you still love watching?
What’s a song you can’t stand listening to?
What movie are you always up for watching again?
What can you add to any movie to make it better?
What do most movies/tv shows get wrong?
What was the worst ending of a movie you’ve seen?
Who would be the best fictional character to have as a best friend?
What TV show went on for too long or is still going on should have been canceling long ago?
What’s your favorite relatively unknown YouTube channel?
If you had to start a podcast, what would your podcast be about?
What shows intro do you always watch all the way through?
What’s your favorite gif?
What music videos made a strong impression on you?
What movie did you watch but still have no idea what it’s about?
What old movie plots just wouldn’t work today because of modern technology?
What TV or movie trope never actually happens in real life?
Who were the most villainous hero and the most heroic villain?
How do you find new shows/music?
What’s the weirdest piece of media you’ve seen or heard?
What’s the best documentary you’ve watched?