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. Show
This article is also available en español. 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. 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! And if these 300 questions aren’t enough we’ve also got questions for couples and questions to ask a guy. TABLE OF CONTENTS
Best questions to ask your boyfriend1. 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. 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 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. 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 real 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 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. 13. 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. 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 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. 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 a fun question to ask. 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
More fun questions: You can also try our fun questions to ask a guy page or our fun questions page. Personal questions to ask your boyfriend
More personal questions: Check out our personal questions to ask a guy or these personal questions. Questions about your boyfriend’s past
We also have a page of topics to talk about that has a section on personal history. Questions about the people in your boyfriend’s life
Relationship questions to ask your boyfriend
Questions to ask about your boyfriend’s worldview
Entertainment questions to ask your boyfriend
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 flagsIf you notice anyone 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 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. What topics you can talk with your boyfriend?Personal Conversation Topics and Questions. When do you feel most confident?. What is your favorite thing about yourself?. Tell me about a time you did something that was outside of your comfort zone.. What do you want people to remember you for when you're gone?. What's your biggest fear?. What do you want out of life?. How do you keep a conversation going with your boyfriend?Get Into A Healthy Debate.. Ask About Their Day.. Make Plans For The Future.. Talk About The Past.. Play The Question Game.. Tell Each Other Exactly How You Feel.. Share Random Thoughts.. Talk About Physical Intimacy.. How can I talk to my boyfriend without boring?Start off a conversation by telling your boyfriend what's on your mind or mention something interesting you've learned recently. Add interesting details to the conversation. Ask questions to keep the conversation going, and always listen closely to what he has to say.
What can I talk about with my boyfriend over call?Try to find some conversation starters to help fill the space. Ask him things such as how his day was, if anything interesting happened, or talk about your experiences, such as favorite vacations, places to visit, foods to try together, childhood memories, etc. You guys still have a lot to learn about each other.
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