Best Friend Quiz
How well do your friends know you?
Never have I ever Play Now

Getting lots of one-word answers from your boyfriend? Well, if this feels familiar, we’re here to help.

It can be tricky to get your boyfriend talking. And even more complicated to start a deep conversation. Having though-provoking talks with him can deepen your relationship a lot, but what if he is really not that of a talkative person?

Sure, some guys love to talk about themselves and will chatter on for days. For this kind of guys, those questions will be great to help you learn a little more about him, get to know him better and find out what kind of person he is.

Either way, we are sure you will have a great conversation with these questions. So let’s get started!

Best questions to ask your boyfriend

1. What would be the ideal 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.

2. 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.

3. 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.

4. How often do you feel entirely 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.

5. 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.

6. 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.

7. 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.

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 really quick. We all have annoying habits, so feel free to share some of yours and give him a heads up.

9. 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.

10. 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.

11. 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.

12. What are the two most significant lessons you’ve learned from previous relationships?

So don’t get jealous of 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.

13. What gross and unhygienic things do people do that bother 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.

14. 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.

15. 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.

16. 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.

17. 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.

18. 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 a funny answer or a clever 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. 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.

20. 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.

21. 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.

22. 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 an entertaining one. You’ll probably get to hear an interesting story. And who doesn’t love a good story?

23. 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.

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.

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.

Fun questions to ask your boyfriend

  1. What silly thing do you take a lot of pride in?
  2. What product are you shocked that no one has made a better version of?
  3. What would change if it was socially acceptable to speak openly and frankly about anything?
  4. What chore do you dread most?
  5. What do people really need to chill out about?
  6. What era’s imagined future would you most want to live in? (i.e., 1950’s lots of curves, chrome, and everything shiny)
  7. Where is the craziest place you have danced?
  8. If you could have a remote control that controls any one type of machine, what would you have a remote for?
  9. What crazy things will you do if you ever become rich?
  10. What’s a lame joke you use on a regular basis?
  11. How often is your brain on autopilot?
  12. What’s the grossest thing you’ve drunk?
  13. If animals were as intelligent as humans, what types of jobs would certain animals be uniquely qualified for?
  14. What’s something you wish you had never learned how it was made or how it works?
  15. What great idea would you like to try if you had enough money?
  16. What should be the next advancement in shoes?
  17. Where and when did you let out your most inappropriate fart?
  18. Should TP hang over or under?
  19. 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?
  20. If you were an action figure, what would you come with, and what would your catchphrases be?
  21. If you were forced into a dance competition, what song would you choose to dance to?
  22. What inedible thing do you wish you could eat?
  23. How often do you go into a room and forget why you went into the room?
  24. What are some non-traditional toppings for ice cream that you think would be pretty awesome?
  25. What would you do first if you gained the ability to fly?
  26. What unnecessary products or services do you consider necessary?
  27. What’s the spiciest thing you’ve eaten?
  28. What’s the coolest thing scientists could uncover while searching the ocean?
  29. If you were given immortality, but there was one condition, what would stop you from accepting immortality?
  30. What’s the best “who would win in a fight A or B” you can come up with?
  31. What do you think aliens would actually look/be like?
  32. What names were ruined for you because you knew someone terrible with that name?
  33. What scrambles your brain every time you think about it?
  34. What’s the best conspiracy theory you can make up on the spot?
  35. If you could change your first name, what would be the most epic name you could choose?
  36. What are you a non-military veteran of?
  37. If you could make a candle with any scent, what type of scented candle would you make?
  38. What website doesn’t exist but should?
  39. What do you love least about the activity you love most?
  40. If you could switch genders for a length of time of your choosing, would you? And if so, how long?
  41. Why do you think we dream?
  42. 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.)
  43. What’s your dream car?
  44. What shortcut do you wish you could take?
  45. What’s legal but still feels illegal?
  46. Which fictional villain made you feel real hatred towards them?
  47. What’s your favorite waste of time?
  48. What would an amusement park filled with your biggest fears be like? What rides would it have?
  49. 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?
  50. If you could be the first person to do something, what would your achievement be?
  51. If you were in a high-speed chase, what song would you want blaring on the radio?
  52. What’s something you do one way even though it’s incredibly inefficient or nonsensical because that’s how you’ve always done it?
  53. How would the world change if health potions existed?
  54. If wars were abolished, what would be the most interesting way for countries to settle their differences?
  55. If you had a secret lair like Batman or Superman, what would it be like?
  56. What event from the past do you most want to see a recording of?
  57. If jobs/careers had slogans, what would be some of their slogans?
  58. What’s the most stress relieving thing you can get/do for less than 20$?
  59. What seldom works the way it should?
  60. What condiments do you refrigerate, and which do you leave in the cabinet/pantry?
  61. If you had complete genetic control over plants, what is the coolest looking tree you could make?
  62. What is the strongest animal you could win against with just your bare hands and feet?
  63. 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?
  64. What’s the last thing you Googled?
  65. What is the coolest flag in use?
  66. How well do you think you would do if you were lost in the woods for two weeks?
  67. How much is the correct amount of ice cream to put on an ice cream cone?
  68. Do fish have necks?
  69. If colors had a taste, what would each color taste like?
  70. What’s the funniest / strangest thing that someone has drunkenly confessed to you?
  71. What would an amusement park designed specifically to make you happy, be like?
  72. 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.)
  73. What’s the weirdest wrong number text or phone call you’ve gotten?
  74. If you started a cult, what kind of cult would you start?
  75. 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.)
  76. Which hairstyles fit with which personalities?

Personal questions to ask your boyfriend

  1. How easily do you change your opinions?
  2. What would your very own personal hell be like?
  3. What makes you feel alive?
  4. What about your appearance would you change if you had the chance?
  5. When did you really try hard, I mean really whole assed it, and it still wasn’t enough?
  6. In what situations do you act least like yourself?
  7. What do you want to get out of life?
  8. How well do you think you can read others’ emotions?
  9. What makes you interesting?
  10. What creepy thing do you do on a regular basis?
  11. What’s the quickest way to make you angry?
  12. How do you fight off procrastination?
  13. What’s the worst dream you’ve ever had?
  14. What’s it like to be you?
  15. What’s the hardest truth you’ve come to grips with?
  16. How often do you get into arguments with people on the internet?
  17. Who or what is holding you back?
  18. What mundane task have you mastered?
  19. What quirks does your body have?
  20. What are you a snob about?
  21. What event made you mature as a person the most?
  22. What is the most alone you’ve ever been?
  23. What do you want to be written on your tombstone?
  24. What do you value most?
  25. How much of the bad stuff that happens to you is your fault?
  26. What’s on your bucket list?
  27. What makes you the happiest?
  28. What word describes you better than any other word?
  29. What would it look like if you fully lived up to your potential?
  30. What would you want your funeral to be like?
  31. How adventurous are you?
  32. What odd thing are you fascinated by?
  33. How lucky are you?
  34. How nurturing are you?
  35. If your life was a book, what would this chapter be called?
  36. How soft are you?
  37. What are you really obsessed about?
  38. When are you the most yourself?
  39. How curious are you?
  40. What steps would you have to take to achieve a dream you’ve had for a long time?
  41. What do you get overly emotional about?
  42. What are some incredibly common experiences that you’ve missed out on?
  43. How neurotic do you think you are?
  44. What about you scares you the most?
  45. What’s your jam?
  46. What sounds fills you with dread?
  47. Who makes you uncomfortable when you are around them?
  48. What brutally honest truth about yourself can you share with me?
  49. What do you fear about the future?

Questions about your boyfriend’s past {his-past-questions}

  1. What’s the most painful text you’ve ever received or sent?
  2. What’s the most uncomfortable thing you’ve had to tell someone?
  3. What were the turning points of your life?
  4. 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?
  5. When was the last time you were really, really wrong about something?
  6. What’s the strangest thing you’ve seen happen at a job you’ve had?
  7. What did you do when you were younger that you still cringe when you think about it?
  8. What’s the riskiest thing you’ve ever done?
  9. What bridges have you burned?
  10. What is your most beautiful memory?
  11. What did you do in the past that people keep bringing up over and over and over again?
  12. What unique games or activities did you play as a child?
  13. What event in your past has come back to haunt you?
  14. What’s the most memorable call you’ve taken or made?
  15. What was your worst injury as a child?
  16. What’s your worst vomiting story?
  17. Who have you purposely cut out of your life?
  18. What’s the most memorable vacation you’ve taken?
  19. What movie title best describes your life so far?
  20. What do you wish you had/hadn’t said?
  21. What was the cleverest thing you did as a child?
  22. Where is the most interesting abandoned place you’ve been to?
  23. When was a time you threw caution to the wind and just went for it?
  24. What have you stolen?
  25. If you could go back and change just one decision you made, what decision would you change?
  26. Where are some places that you’ve been that you’ll never be able to go back to?
  27. What’s the coldest you’ve ever been?
  28. What’s something that has changed you for the better and something that has changed you for the worse?
  29. How much have you changed in 5 years?
  30. Who is the nicest person you’ve ever met?
  31. What are some things you hid from your parents?
  32. What was the most awkward moment you had at school?
  33. What’s the most American thing you’ve ever done? (Regardless of whether are American or not.)
  34. What story that involves you has probably been told by most people?
  35. What’s the most famous you’ve been?
  36. What were some of your favorite childhood books?

Questions about the people in your boyfriend’s life

  1. Who in your life has the most positive outlook on life?
  2. How often do you talk to your extended family?
  3. What secret is someone keeping from you, but you already know all about it?
  4. What was your closest friendship that fell apart?
  5. How well do your family members get along?
  6. Who’s the most difficult person you must deal with on a regular basis?
  7. Who do you know is full of unfounded confidence in their opinions?
  8. What happened to your best friend from elementary school?
  9. What’s the most awkward thing someone has said to you?
  10. What plausible new rumor can you come up with on the spot about a celebrity or friend in your circle of friends?
  11. When was a time that you thought you knew someone, but they turned out to be an entirely different person?
  12. Who in your life is most likely to be a serial killer?
  13. What are some scandals that happened in your circle of friends?
  14. What stupid things have you convinced friends to do?
  15. Who’s the black sheep in your family?
  16. What are the three most important things you learned from your parents?

Relationship questions to ask your boyfriend

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

Questions to ask about your boyfriend’s worldview

  1. What did you reluctantly try one time and then became a die-hard fan of?
  2. What have you boycotted?
  3. What would your child have to do for you to disown them?
  4. What is the worst emotion?
  5. What is the saddest story you know from history?
  6. What lie do you wish you never learned the truth of?
  7. Where would your perfect place to settle down be?
  8. What do people most often take for granted?
  9. Where are some places that got much better or much worse due to technological advances?
  10. What quote are you sick and tired of hearing?
  11. 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?
  12. What are you surprised a lot of people don’t know how to do?
  13. 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?
  14. What would be the worst text to wake up and see?
  15. Who is the closest to being a perfect human?
  16. What do you need advice about?
  17. Is ignorance bliss?
  18. When is it better to act first and ask for forgiveness later?
  19. What’s the best way to travel?
  20. What’s something small that makes a big difference?
  21. What used to be only for the rich but now is mostly associated with poverty?
  22. What was the biggest lie your teachers told you when you were in school?
  23. What would be the most useful mandatory class to add to public schools?
  24. What do you wish someone had told you, so you didn’t have to learn the hard way?
  25. What is the dumbest thing that a lot of people believe?
  26. What do you find yourself getting into arguments about most often?
  27. What behavior makes you think someone has a lot of class?
  28. What’s the prettiest thing you’ve seen someone do?
  29. What does the world need more of?
  30. What makes you feel old?
  31. If you found out you were wanted for a murder you didn’t commit, would you turn yourself in?
  32. What’s the silliest social issue people get up in arms about?
  33. 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?
  34. If you see money on the ground, where is the line between you picking it up and you not picking it up?
  35. What do you think has gotten too socially acceptable?
  36. What are some of your personal tips on how to live a remarkable life?
  37. What’s the most worthwhile thing a person can spend their time on?
  38. Who do you aspire to be more like?
  39. What did you see online that still haunts you?
  40. What’s the most frustrating thing you encounter daily?
  41. What’s the most disturbing thing you’ve come to accept?
  42. What makes a person seem ignorant or intelligent?
  43. What off-handed comment a parent made has stuck with you through the years?
  44. What do you wish you could stop doing?
  45. What can someone say that always makes you cringe?
  46. What minor inconvenience bothers you way more than it should?
  47. What’s the biggest waste of money?
  48. What bad experience should everyone have to go through?
  49. What is considered normal and is accepted but really shouldn’t be?
  50. What was the most intriguing internet mystery you’ve come across?
  51. What’s the most annoying question you get asked on a regular basis?
  52. What social issue deserves more attention?
  53. When was the last time you felt your perception of reality shift in a major way?
  54. When in history was the best time to be alive?
  55. What do you think is the best period of a person’s life?
  56. What’s the best advice you’ve ever been given?
  57. What advice do you think the future you would give current you?
  58. What group of people do you find it impossible to take seriously?
  59. What do you think will cease to exist during your lifetime?
  60. What industry is in denial about being obsolete?

Entertainment questions to ask your boyfriend

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

So that’s the end of the list of questions, but I’ve got a little bonus for you! Below are some things you want to watch out for, relationship red flags.

Boyfriend red flags

If you notice any of these in your boyfriend, it’s a big red flag. Don’t ignore it. You need to seriously consider whether you want to continue the relationship. I would actually just recommend breaking it off if you notice any of these. Better some pain now than a lot of pain later and a messy divorce/breakup.

His failures are always someone/something else’s fault.

Usually, this type of person can’t see that they are the cause of their own troubles, that they could have avoided their troubles by taking action, or that they can actually fix their problems. Because they don’t see themselves at fault for anything, they don’t see any reason to improve or change.

He’s mean to animals or people for no reason or because it’s funny.

This probably means they have a serious cruel streak in them. And they will be cruel to you too if they haven’t started already. I’ve never seen a person become less cruel, so don’t expect your boyfriend to. Just get out now while you still have a chance.

He lies a lot about insignificant things and doesn’t admit he lied when confronted with evidence.

Not normal lies to avoid trouble. That’s pretty common. I’m talking about weird lies for no reason. Like telling you about an uncle, they don’t actually have or lying about how they got a particular shirt for no reason.

Seriously, just run. I’ve run into this several times. The small lies are the ones you found out about. There are bigger lies. And you have no idea what is a lie and what is the truth.

Everyone else can’t see what you can, they can’t see how great of a guy he is.

Yeah, you probably can’t see the forest for the trees. We’ve all been there. You are in love, so you gloss over their faults. But if everyone around you doesn’t like your boyfriend or tries 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, like you were someone else looking at him and how he acts. And don’t make excuses for any truths you see.

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Conversation Starters & Icebreakers

The PsyCat Games magazine topic conversation starters & icebreakers is dedicated to the best questions to start a great and interesting conversation for girls and guys. You can also use those questions for your first date or even a reunion with your friends at a party.