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.
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!
List of questions to ask your boyfriend
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 like 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.
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.
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?
Who’s the black sheep in your family?
When was the last time you were really, really wrong about something?
How neurotic do you think you are?
What are you really OCD about?
What’s the silliest social issue people get up in arms about?
What social issue deserves more attention?
How well do you think you would do if you were lost in the woods for two weeks?
What’s the best way to travel?
What bridges have you burned?
What does the world need more of?
Is ignorance bliss?
Who or what is holding you back?
Where would be you perfect place to settle down?
What are the three most important things you learned from your parents?
What shortcut do you wish you could take?
What is the role of a wife?
When are you most comfortable?
What makes a person seem ignorant or intelligent?
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?
What’s your favorite waste of time?
What’s your dream car?
What’s the best advice you’ve ever been given?
What minor inconvenience bothers you way more than it should?
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.
Relationship red flags
If 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.
Snapshot of the previous 25 questions (not the extra questions)
And here is a printable PDF of all the questions.
Well I hoped that helped! If you need any more questions you ask, I’ve got more than enough!
More questions to ask your boyfriend…
- Questions to ask a guy – These are some great general questions to ask a guy. Solid conversation starters for any guy, including your boyfriend.
- Would you rather questions for your boyfriend or girlfriend – Some more questions to ask you boyfriend, this time they are would you rather questions!
- Questions to ask your girlfriend – Here is the companion article to this one. Even though it’s for girlfriends, there are still some solid questions that’ll work for boyfriends too. Also, make sure to check out the red flags at the bottom of the page.
- Personal questions to ask a guy – These questions are great for getting to know even more about your boyfriend.
- Funny questions to ask – If it’s getting a bit too serious, you might want to try these lighthearted and silly questions.