200 Questions To Ask A Guy To Get To Know Him Better
Okay, we know that guys are from Mars and impossible to read, but if you want to stand a chance with the new man in your life it’s important that you take the time to get to know him better. In this bumper article, Beauty and Tips have got 200 questions for you to choose from that will give you a better insight into who he is.
We live in a fast-paced world where a hamburger is ordered and delivered to our table in minutes, a coffee can be made in seconds, and dates are available on tap. After a swipe and a few messages, you could be meeting a brand new guy within 24 hours of swiping.
And who cares if it doesn’t work out? With that kind of speed, you could date 4 different guys in a week! Eventually, you’re sure to meet someone you click with.
See, we now live in the digital age which is also the age of abundance. If a guy doesn’t grab our attention and capture our imaginations immediately, it’s okay because we’ll just move onto the next one. It’s no big deal.
However, many of us are doing ourselves a disservice and not giving each guy a chance. Safe in the knowledge that we’ve got lots of other matches we could be talking to instead, we don’t take the time to truly get to know anyone. We go on one date and decide he wasn’t right for us.
And why not?
“Oh, he didn’t like ham.”
“He prefers coffee over tea, hmmmm.”
“He loves his mom too much.”
“He doesn’t like Prosecco! Of really?!.”
It hardly helps if you don’t ask him the right questions. On the surface, he might not appear to be your type and that’s fine. But if you start asking the right questions, you might find out that there’s more to him than meets the eye.
The right questions give us the answers we need. They help us to decide whether a guy is the right one for us, or whether or not we need to move on as soon as possible. Questions save us time by revealing how compatible his values are with ours and whether or not this relationship has got legs.
(We also have a great and useful article that is quite similar: 400 questions to get to know someone deeply, you can read it here.)
Let’s take a look at 200 questions to ask a guy to get to know him better.
What’s The Longest Relationship You’ve Had?
This shouldn’t be the first ever question you ask a guy, and indeed it shouldn’t be one of the first. Ask it too soon and you start venturing into dangerous waters where he starts to think about his ex.
Which is the last thing you want him to do.
Discussing past relationships is usually out of bounds during the getting-to-know someone period but there comes a time when you do need to talk about the elephant in the room.
This is an important question because you do need to know how committed to relationships he is … and whether or not he’s just a player who gets cold feet.
If he’s never been in a relationship that’s lasted longer than a year, you should be on your guard. It shows that he’s never been emotionally mature enough to stay with them for long enough.
Either that, or he’s got issues.
If you’re looking for a long-term relationship, it’s a good idea to start dating someone who’s had at least one long-term relationship in the past, especially if he’s at least 30 years old.
Do You Like Hugs?
If he doesn’t like hugs, you should probably bail out right away.
I mean WTF.
What Were You Like As A Child?
Get him to open up about his experiences as a child and you’ll really start to get to know him better.
What is a major turn off for you?
Before you start dating him properly, you need to find out what majorly turns him off. Maybe he doesn’t like feminism, veganism or when women snore. Who knows?
What food do you always avoid?
Does he avoid fruit and veg or is he a health freak who won’t touch anything fun?
If so, try and tempt him with a donut WE’RE KIDDING DON’T BE MEAN.
What is a real man for you?
No doubt you’ve got your own definition of what a real man is, but it will be interesting to see how he defines one.
Would you go back in time if you could?
Let’s face it, we’d all love to go back in time – but which moment in history would he go back to?
When Was The Last Time You Did Something Spontaneous And What Was It?
Especially if you’re a spontaneous person yourself, you’ll want to date someone who doesn’t mind going with the flow. As such, this is a key question as it will reveal whether he’s the adventurous type who love a last minute thing, or whether he’s restrained and has to plan ahead.
It’s also a really fun question that can start a cool conversation. He’ll (hopefully) relate an interesting story that gives you a clearer picture of the life he’s lived and the things he’s done.
Let’s just hope his answer isn’t too out there and you have to pull your “are you for real?” face.
Do you believe in aliens?
Does he believe in any kind of conspiracy theory for that matter?
It would be kind of cool if he said that he does indeed believe in aliens and that – even better – he’s been abducted.
Wouldn’t that be a cool story for a first date?!
Would you live on the beach, in the city or in the country?
Is he a beach bum, a city slicker or a country bumpkin? Could he live by the ocean without any care in the world or does he need people?
Or maybe he wants to give it all up and live in the middle of no where?!
How important is work for you?
This is a key question because, for some guys, work is pretty much everything. And this kinda sucks for their girlfriends.
Find out how many hours he works and whether or not he has a good work/life balance. If he doesn’t, it might be time to call time on him already.
Are you naughty or nice?
Is he a devil or an angel?
What would you rather he was?!
What Is The Thing You’re Passionate Most About Right Now?
This is a really significant question because if he answers with something lame like “Not much, I’m just looking to get back into dating and make a girl the thing I’m most passionate about,” it tells you that his life lacks purpose and that he’s the clingy type.
Think about it: If he has no passions, you’re going to become his passion if you start dating him. And that wouldn’t be cool.
It’s important that a guy has passions – things he love to do, things that drive him, motivate him and give him meaning. It would be really cool if you share his passions but it’s fine if you don’t. His passions can be something he shares with you, teaches you about and so on.
There’s nothing like a guy who’s passionate about something, honestly.
What Movie Would You Have Loved To Be In?
We love this question because it’s super duper fun.
Guys love it too because it gives them the chance to fantasise about playing their favourite action hero in a film.
And hey, maybe he’ll say that he would have loved to have played Jack in Titanic who sacrifices himself for Rose. Aww. In which case, you know you’ve got a keeper.
On the other hand, he might say that he would have loved to play The Joker in The Dark Knight who kills lots of people.
What are you absolutely rubbish at?
Come on, this is an AMAZING question.
What cartoon would you still watch now if it was on TV?
Whatever he answers, he definitely still watches it every day.
Who do you get along with most?
Does he gel with a friend, a family member or perhaps a colleague?
Do you still speak to your exes?
Tricky question to ask but kinda important. So ask it but only when the time is right.
What do other people think of your fashion choices?
He might think he looks smooth – but does anyone share his opinion?
Do You Ever Do Random Acts of Kindness, and if So, What?
Could you imagine if he answered, “No, I owe the world nothing” to this question? Psycho.
Let’s hope he commits random acts of kindness and let’s hope they’re really sweet.
Otherwise, you’ve got a mean man on your hands.
What Do You Fear The Most?
Like some of the other questions on this list, this one shouldn’t be asked too soon. Why? Because it means you guys are talking about negative things too soon.
It’s still an important question to ask, of course. Not only are you showing him that you’re interested in him and want to get to know him better, but you’re also furthering the conversation and – if possible – you might be able to show him how his fears are holding him back.
Plus, you need to find out as soon as possible if he’s as scared as spiders as you are. If he is, he’s definitely not boyfriend material.
(we’re kidding – although, who’s going to get rid of all the arachnids?)
What’s the best gig you’ve ever been to?
Even if he doesn’t go to too many gigs now, he will have been to a few gigs in the past. So take him on a trip down memory lane and see what music he was into when he was younger.
And pray that his tastes aren’t too cheesy!
Have you ever been in a fight?
Are you dating a lover or a fighter? Is he one for a brawl or does he prefer to play the peace maker?
How important is it that girls are funny?
Some guys love it when girls are hilarious, but there are some guys who literally need their girlfriend to be funny.
If he’s one of them and you’re not funny at all RIP you.
Would you tell a friend if they were out of line?
Does he stand up to his friends and tell them when they’re out of order? Or does he say nothing because he doesn’t want to fall out with his buddies?
Are you a night owl?
Is he up until the wee hours or does he like to go to bed early?
And if he stays up late, what is he doing?
Do you believe in reincarnation?
Imagine if you guys had met in a past life?!
Find out how “out there” his spiritual beliefs are and whether or not they’re compatible with yours.
What’s Your Family Like?
Again, you don’t want to ask this rather personal question too soon as it might seem as though you’re coming on too strong and already want to meet his family.
However, lots of people share the same values as their family. To get a better understanding of who he is as a person, it’s a good idea to find out what his family is like.
If you’re a family-oriented person, this is a super important question because you’ll also find out if his family sounds like the kind of family you and your parents would get along with, and you’ll also find out if he even still sees his family.
What would you spend more time doing if you had lots more free time?
And don’t say “train spotting”, dude.
Would you like to be a millionaire?
Or is money not important to him?
Do people laugh at your jokes?
Don’t ask this immediately after he’s just told you a joke.
Did you do well at school?
Or was he a rebel who never even went to class?
Would you go into space if you could?
Or is he happy here on earth where it rains all the time?
What’s The Stupidest Thing You’ve Done?
Look, we’ve all done stupid things so it’s not like you’re going to judge him for whatever he’s done.
Maybe he tore his clothes off and ran across a football field naked.
Maybe he pressed the “emergency fire” button on an airplane once.
Or maybe he lost his passport in Thailand and created a fake one.
Or maybe he’ll confess his true sins to you.
Either way, this is a fun but serious question that will get him to open up a bit more to you. Which is exactly what you need at some point.
What Are Your Bad Habits?
Very few people are going to want to give away a list of their bad habits when they’re trying to get know someone new. This is why it’s important that you tell him at least one of your bad habits first. Show him that you have no problem with sharing some of the gross (okay don’t make them too gross) things you do.
And then ask him for some of his bad habits.
Remember, once you’ve asked this question there’s no going back. If he answers “I snore and talk in my sleep all the time,” or “I EAT FOOD WITH MY HANDS” you can’t stare at your phone screen for an hour before never texting him back ever again. After all, he put his neck on the line for you.
Ask the question only if you dare.
Otherwise, wait until you guys actually start dating for real and find out the natural way.
What did you want to be when you were a kid?
Don’t all small boys want to be firemen or sports heroes?
What did you used to love doing but would never do now?
Gotta be beer pong.
Unless he still does that every night.
What instrument would you love to learn how to play?
If you could bring a celebrity back from the dead, who would it be?
Gotta be Michael Jackson!
Is There Anything From Your Past That You’d Do Differently?
We all have a past. We’ve all done things that have made us proud and things that make us wince.
But you know what? Not all of us have regrets. Some of us look back on our mistakes and see them as life lessons. Would we do things differently? Some of us definitely would (why on earth did we turn up to a first date wearing a Cher leotard?!) but others know that each mistake we made was a lesson that taught us how not to do things in the future.
Achievements and mistakes are what make us who we are. So prepare for your guy to give you a really boring answer along these lines!
That said, he might also tell you a few things that he’d do differently if he was given a second chance.
Let’s just hope his mistakes weren’t too bad …
Are your parents proud of you?
Aww, let’s hope so.
Which actor should play you in a movie?
His answer is probably going to be hilarious.
That’s what they all say, dear.
What one thing would make your life better?
Would it be cool or weird if he said dating you?
What Is Your Best Physical Feature?
Do you know what guys LOVE to talk about?
Football? Well, of course.
Beer? That goes without saying.
But what they really love to talk about is themselves.
Girls are the same. Who doesn’t want to talk about themselves? Get a guy onto his favourite subject – himself – and he could literally chat for hours, especially if you keep on plying him with questions about himself.
So go ahead – ask him what he thinks is his best physical feature. He’ll absolutely revel in the question and let you know that he loves his eyes and that his lips are just darling.
Then there are his arms that he doesn’t mind, while people always seem to compliment him on his hair.
Etc etc etc!
How Do You React When Things Don’t Go Your Way?
This is a great question that gives you a powerful insight into what kind of person he is. Does he stay calm under pressure? Does he look for solutions or does he focus on the problem?
We are not defined by what happens to us but by how we respond to what happens to us. Pay close attention to his answer because it will give you a massive insight into what his character is.
For example, if you’re a goal oriented person, the last thing you’ll want is to date a guy who kicks and screams when things don’t go his way.
The best answer a guy could give here is that they take a time-out to calm down, breathe and look at the situation anew so that they can find a better answer. Either that, or they take the time to change their biochemistry .. or simply call it quits for the day and do something that makes them happy.
Would You Rather Go Deaf Or Blind?
This always seems like a silly question but you’ll be amazed at some of the intelligent, thoughtful answers that people come up with.
Ask him this and he’ll either come up with an intelligent, thoughtful answer of his own, or he’ll make you laugh with something funny.
For example, maybe he’ll say he’d rather go deaf because if he goes blind he won’t be able to see all the crumbs on his shirt.
Or maybe he’s just not as funny as us.
What’s The Toughest Thing You’ve Had To Deal With Mentally?
This is a great question, but like other questions on this list it’s one that needs to be asked a little bit later on. It’s too emotionally involving of a question to ask on the first date.
Whatever answer he gives, he’s going to be mentally transported back to what was a difficult, emotional time for him, so you need to be prepared to support him through his answer. If he struggles, don’t be afraid to hold his hand or hug him.
People have dealt with many tough things in their lives, from bereavement to losing their jobs.
Be prepared for him discussing a past relationship, too.
Do You Like Your Job?
It would seem that most people don’t like their jobs, but who knows? Maybe you’ll strike it lucky and meet a guy who happens to love his.
Either way, even when we absolutely hate our jobs we seem to like talking about them. It gives us a chance to have a good moan!
And when you start talking about jobs and careers, you can steer the conversation towards ambitions, hopes and dreams.
If you could read peoples’ minds, would you?
Is he going to be really creepy and admit that he totally would? Or does he respect peoples’ right to privacy?!
Are you goal oriented?
Does he believe in setting goals and achieving things in life, or does he prefer to just go with the flow and see where it gets him?
Have you ever cheated on an exam?
Let’s hope he has.
What?! It’d make for a great story! Especially if he got caught. What happened next?!
Do people describe you as a caring person?
Okay, you’ve heard him talk about himself, but in order to get a better idea of what he’s all about you need to find out what other people think of him.
If you were to change your name, what would you choose?
Is he going to pick something absolutely ridiculous like Prometheus, or something as low key as Brian?
His answer will give you a further insight into his personality.
Do you leave tips at a restaurant?
Or does he keep all his spare cash to himself?
What’s the biggest lie you’ve ever told?
Come on, he’s definitely told a few lies in his life. What was the biggest one?
Do You Believe In God?
Do people still ask this question? They sure do.
Does this question still matter? It depends how important it is to you. Some people won’t date a person who’s totally ruled out the possibility of God, while others would never date a religious person – and especially not a religious nut.
Some, however, can take it or leave it. They might believe in a God of some kind but it doesn’t matter if their partner does or doesn’t.
Either way, the question can lead you down a path of theological and philosophical discussion. If you want that, go for it.
On the other hand, if you want to avoid that kind of stuff, it’s best if you don’t ask this question.
What Is Something You’re Good At?
As we’ve already mentioned, guys love to talk about themselves. So as well as getting him to talk about his best physical features, ask him what he’s talented at.
We’re attracted to men with talents, so find out where he’s skilled. Maybe he’s a bit of an artist, or maybe he’s got a secret gift for sculpting.
Or maybe he’s just an excellent judge of character. In which case, watch out!
What Are Your Friends Like?
If the two of you are going to be dating properly, you may as well take the time now to find out what his friends are like. After all, you’ll be meeting them soon enough and you’ll need to be prepared!
This is also a key question because it helps to give you a further insight into what he’s like as a person. We judge people by the company we keep. If he describes his friends as a bit misogynistic and a bit loud and weird, you need to be on your guard.
On the other hand, if he describes his friends as kind, loyal and generally amazing person then awesome!
Are you content right now?
Is he content with what he has in life right now, or is he itching to take off on another adventure?
Is he comfortable or does he want more out of life?
If you could have one super power, which one would it be?
Ah, the old super power question. He’ll be expecting this.
Just make sure his super power doesn’t outdo yours!
When did you have your first kiss?
Is he a Romeo who had his first kiss in high school?
Or did he have to wait until college?
Or – OW – is he still waiting?
This is a great question that could inspire a hilarious answer.
Do you ever return products that aren’t good enough?
Is he the kind of person who won’t stand for shoddy service? Or does he keep quiet because he doesn’t want to create any hassle?
Do you stand up for what’s right?
How he answers this could have a pretty big bearing on how you feel about him. After all, women want a man who’s going to stand up and be counted, as opposed to a boy who hides away and doesn’t take responsibility or accountability.
After all, what will he do if you’re the victim of a verbal attack in public? Is he going to defend your honour or hope things blow over as soon as possible?
Do You Make More Good Decisions Than Bad Ones?
Oh, you’re really putting him on the spot with this one.
Does he judge situations well or terribly?
Does he know what his values are so that he always makes the right call? Or does he have zero values, which is why he’s always making bad decisions?
His answer to this needn’t be a deal breaker, but if he’s the kind of guy who keeps making bad decisions, you’ll be wandering why. What you’d really like is a guy who makes more good decisions than bad ones.
What Do You Do At The Weekends?
Because you need to know if he’ll be going fishing or taking you out for a walk and a meal.
This is important!
Weekends are that time of the week when we get to spend more time with the person we’re dating. If that person prefers to devote time to strange hobbies than see us, or if they’re a total sports nut, then we need to know as soon as possible.
If weekends are important to you but mean nothing to him, it could be a deal breaker.
What Lifts Your Mood?
This question gives you huge insight into what makes him tick. Does cheesy eighties music bring his mood right back up? Or does he have to book a holiday to America to make him feel better?
Or maybe he gorges on pizza and burger?
Or perhaps – just perhaps – seeing his girl is enough to pick him up instantly.
If so – aww.
When Did You Last Cry?
If he answers this with “I never cry, baby,” he’s lying.
All men cry at some point. It’s in them. They’re as vulnerable as us. It’s just that they show it a lot less.
Pop this question to him. If he looks away when he says “Girl, I never cry,” he’s totally lying!
On the other hand, if he bares his soul and tells you he cried four times in the last week then, um.
Do You Want Kids?
Again, like a few of the questions on this list, this isn’t a question you should be asking right away. Leave it for a few weeks.
That said, if you want kids yourself, you don’t want to leave this question too long. After all, you don’t want to waste your time with someone who never wants kids. It’s an important question and you need to know his answer. But just make sure you get your timing right because, even though he might want kids, if you ask this too soon you’ll scare him off.
What One Thing Do You Want To Do Before You Die?
It’s hardly a morbid question gets you both thinking about death. Rather, this question is designed to get him to open up about the things that matter the most to him.
What is his overriding ambition? What is his biggest goal? Is it to see the his favourite team in the Super Bowl? Or does he have loftier ambitions?
Perhaps he wants to go to space or complete get a Masters?
It’s a big question that will reveal a lot about the man you’re dating.
Can You Cook?
Basically, can you cook or are you going to burn my house down if I let you make toast?
A few years back, we’d wager that most men couldn’t cook. These days, however? Things are a lot different and men are more adept in the kitchen than they ever used to be.
Is this really an important question? Maybe not but it gives you an insight into the man and whether he’s taken the time to acquire a pretty damn useful life skill.
Moreover, if he can cook just think about all the amazing dishes he might make for you!
And if he can’t cook, well, yes, it might mean that you’ll be taking care of all the meals 🙁
What’s Your Guilty Pleasure Food-Wise?
Is he a burger and fries kinda guy, or does he indulge in ice cream late at night?
Or maybe he sometimes has donuts for breakfast when no one’s looking.
Find out what foods he loves to gorge on and see if you need to be more embarrassed than him.
Then plan ice cream nights under the sheets …
Come on, you were always planning that.
Are You A Morning Person?
This is kinda of an important question if you happen to be a morning person. If it turns out that he never gets up earlier than noon unless he has to, whereas you prefer to rise before the sun, it’s probably not going to work out.
Plus, you can gauge how goal-oriented someone is by how early (or late) they get up. If they could literally stay in bed all day long, it hardly screams ambition.
If You Wrote a Book About Your Life What Would You Title It?
This is sure to provide a comical answer and should go someway to revealing how he feels about his life so far!
It might also reveal his arrogant side, especially if he coins a title such as “I Am Awesome” without a trace of irony …
Where Do You See Yourself In 5 Years?
True, even some ambitious people don’t plan 5 years ahead because they know the world is constantly changing and they need to adapt. But it’s still an interesting question that can go some way to revealing how compatible you guys are.
For example, if he says he sees himself in America in 5 years time and you HATE America, this relationship thing is probably not going to work.
Neither will it work if he says he thinks he’ll be dead in 5 years.
Do You Believe In Ghosts?
It’s a good question because it gives you an insight into how spiritual or mystical he is.
Or whether he simply believes that when we die, we die and that’s it. There is no afterlife, no ghosts and nothing supernatural.
Seriously, though, he might regale you with tall tales of that time he heard footsteps upstairs when no one else was in the house except him …
Do You Ever Tell Lies?
What is this, an interrogation?!
Not a necessary question and you should only ask it in the right context.
For example, don’t ask it if he already thinks you’re having trust issues with him. It could hit a nerve!
Other than that, all the strongest and healthiest relationships are built on honesty and for many people this is an important question.
Do all people lie? Maybe. Is he going to admit he’s told lies in the past? Or is he going to tell you how much of an angel he is? Hmm.
What’s The Best Thing About Being You?
Ask him this question and sit back while he brags about himself for 10 minutes or more.
“Oh, you know, there are many great things about being me.”
Either that or he’ll be incredibly humble.
Either way, you’ll (apparently) find out how truly amazing he is – or at least thinks he is.
If You Could Be A Kid Again, Would You?
Oh, sorry. Thought you were asking us.
This great question will (hopefully) provide a very measured response by the guy. Perhaps he enjoyed being a chid but would never go back because he’s always moving forward in life, or perhaps he absolutely would go back in time and be a kid again because he’s basically a big kid now anyway.
Do You Take Risks And If So, What Kind?
Ideally, you want to know if you’ve got a risk taker on your hands or if he’s the kind of guy who plays it safe.
Moreover, if he is a risk taker, you’ve got a right to know what kind of risk taker. Does he take risks with his career, his investments, his finances, his dates or what?
If he takes risks with his cash it might be a red flag.
However, he answers it you’ll know a bit more about how compatible you guys are.
What’s Your Political Leaning?
This is definitely not a necessary question for everyone and we know that some people do all they can to avoid all talk of politics, especially with the people they’re dating. If this is you, it’s totally fine – you can skip this question.
However, some of you will be dying to know what his political leaning is, and if you’re not the type who easily gets drawn into a vicious political argument, you should go ahead and pop this loaded question.
Truth be told, if his political interests are very different to yours, at least you’ve found out sooner rather than later, right?
Do You Have A Best Friend?
Best friends are awesome. Perhaps you think this is a silly, redundant question – after all, doesn’t everyone have a best friend?!
Possibly, but it’s still a good question to ask because it will inspire conversations about all your friends.
“Ah, I remember the time me and (insert best friend here) went to a party dressed as Peter Pan and Captain Hook because we thought it was a fancy dress party. It turned out that it wasn’t and we looked absolutely ridiculous …”
What Do You Think Is True That Other People Think Is Crazy?
This is a good question but it might take him a while to think of an answer.
A possible answer to this might be “everyone can get rich in 2018 if they try hard enough.”
However he answers, you’ll discover how much he’s prepared to go against the grain and not follow the crowd with his thoughts.
Are You A Worrier?
Some people are worriers, some aren’t. Ask him this question and find out how anxious he gets, or if he takes everything in his stride.
Then decide what answer you like the best.
Ask follow up questions, too. If he worries a lot, why does he worry? If he literally never worries about anything, why not?
Do You Watch The News?
Remember when you were called a dunce because you never watched the news?
Watching the news is kinda important if you want to keep up with current affairs but it definitely doesn’t make you smarter. If he doesn’t watch the news, it might be because he’s focused on other things that matter more to him, such as personal development, or he might just hate all the negativity.
Or he might have realised that he can’t change the news, so why give it so much time and attention?
Are You A Confident Person?
If you’ve been dating or talking to him for a little while, you should know by now whether he’s a confident person or not.
Then again, all you can base your judgements off are what you’ve seen. To all intents and purpose, he might appear to be a really confident person, but it could all be an act. Ask him this question to see how he sees himself in the world. Is he super confident? Or does he fake it?
Or maybe he just plays to his strengths as much as he can?
What Would You NOT Do For A Million Dollars?
Oh, great question. Does he have scruples? Or has he no shame?
Would he run through a pig sty naked for cash? Or has he got some dignity?
It’s a fun question that could raise some pretty serious points.
Plus, you might find out if he’s prepared to cross a moral line for money.
What Personality Trait Do You Hate The Most In People?
Let’s face it, there’s every possibility that he’s going to spend all day answering this question!
It could be that he hates stubbornness, hypocrisy, lying, anger issues …
However, get him to pick just one and ask him why he hates it so much.
What Personality Trait Do You Hate The Most In People?
What, in his opinion, makes people magic? What draws him to them? What fundamental personality trait does he look for in his friends, family and women?
Does he love a sense of humour? Humility? Kindness? A willingness to forgive and forget?
Once again, make sure he doesn’t give you a billion answers. Get him to stick to just one.
What For You Is Unforgivable?
We all have something we could never forgive. Some of us won’t forgive a cheating spouse. Others won’t forgive lying to our face.
But we’re all different. Some will forgive cheating but won’t forgive reneging on a promise.
Ask him what’s irredeemable in his eyes. What is the one thing someone must NEVER do if they want to keep him around?
He’ll most likely explain his answer, taking you into his past with him and inspiring discussion about what’s forgivable and what isn’t.
What’s the most ridiculous thing you’ve ever done?
Find out just how crazy this dude can be!
Have you ever been arrested?
Time to find out if he’s a guy you can introduce to grandma.
Are you an introvert or extrovert? Or a bit of both?
What sucks the most about getting older?
What do you miss the most about childhood?
What’s A Good Year To You?
Awesome question! Is he the kind of guy who’s happy as long as he’s got his health, gets to have a holiday, enjoys a few nights out with the lads and has a girlfriend to come home to?
Or is he more goal oriented? Does he have to achieve new things and do better than he did last year before he considers a year to be “good”?
His answer will certainly be interesting and it will give you a massive insight into whether you’re with a guy who likes to get up and do stuff, or who’s content to be happy providing he’s got everything he needs – love, good company and his health.
Have You Fallen Out With Friends In The Past?
Okay, sure, we’ve all argued with our friends in the past. But what you’re asking him here is whether his arguments have led to a complete break in the friendship. Has he lost friends in the pas due to bitter arguments? Or there people he never speaks to anymore?
How Do You Handle Negative People?
Does he keep them hanging around? Or does he move past them and forwards, onto bigger and better things?
Does he talk to them and tell them they need to be more positive? Does he absorb their negative?
Is he a negative person himself?
This is a key question because most people will agree that they need to move on from negative people as soon as possible. If we keep them around too long, their negativity could start to infect us.
What Keeps You Awake At Night?
It’s a purely hypothetical question because – as we all know – guys are always asleep at night! As soon as their heads hit the pillow, that’s it; they’re gone, snoring the night away.
However, this question is purely to gain a bigger insight into what they care about the most right now.
Or perhaps it will give you an insight into what they’re worried about the most right now.
Does climate change keep them up at night? World poverty? Bills?
Or does the Super Bowl this weekend keep them awake more than anything?
Hey, no big deal if sports and entertainment is what keeps him awake more than world peace. If he’s a fun guy who hasn’t got the time to take the world’s issues on his shoulders that’s his choice.
Where Do You Wish You Were Born?
Lots of people have been born somewhere and wished they’d have been born somewhere else. Usually it’s down to climate, opportunity or because we wished we could have followed in the footsteps of our hero.
Perhaps he wishes he’d have been born in Hollywood or maybe he would have loved to have been born in a Greek island. Ask him this question and find out!
And if he says he wishes he could have been born somewhere like North Korea, then, Ok …
If You Died Today What Would Your Greatest Achievement Be?
Okay, no one really wants to think of themselves literally dying today but it’s still an interesting question that will give you an insight into how successful he thinks his life has been so far.
He might treat the question with self-deprecating humour, in which case it’s totally fine.
On the other hand, your question might make him realise that he’s achieved nothing so far.
In which case, be prepared for the tears.
Hey, we did warn you.
What’s A Relationship Deal Breaker For You?
We all have relationship deal breakers, so why not find out what his are so that you know what you’re dealing with?
Guys tend to keep things close to their chest during the early stages of dating. They might let things slide that, ordinarily, they don’t like.
Then, as time passes, they’ll bring it up. And you’ll be all like “why didn’t you tell me sooner?”
Find out as soon as possible what his relationship deal breakers are so that you don’t run the risk of wasting your time with a guy who doesn’t like women who sing in the shower (what is the deal with not liking that?!).
Who Are You Closest To?
Imagine if he says “my dog” …??
How CUTE would that be?
Seriously, though, this is a good question. If he’s close to his parents, you know you’ve got a winner.
Then again, you don’t want him to be too close to his mom. We know what moms are like when their boy gets a new girl!
What do you hope to accomplish this year?
Besides dating you, of course?!
Seriously, it would be cool if he had goals, dreams and ambitions.
Have you ever seriously offended someone?
Either by mistake or on purpose?
Do you believe in soul mates?
Or are you literally not romantic at all?
What makes you happiest?
Find out what makes him smile more than anything else.
Have You Ever Nearly Died?
Woah! Bit morbid much?
Not really. This actually opens the way for him to tell you a truly amazing, heroic story about the time he charged into a house fire to rescue four kids and their mom before dashing out just before the flames got him.
Or not. Instead, perhaps he’ll tell you about the time a cat nipped his finger and he thought he might die.
Does Growing Old Bother You?
Amazingly, growing old doesn’t bother some people. They go with the flow. They’re too sure of themselves and confident in their own skin to be bothered by something as “minor” as the ageing process.
Some people, however, get really bothered by the idea of growing old. If he’s the type of guy who panics at the sight of a grey hair, you could have a lot of fun with this question.
“You know, when I first saw you I thought you were older than you are …”
What’s your favourite ice cream?
This is probably the most important question on this list.
What do people think is weird but you don’t?
Only ask this question if you can live with the answer.
Which countries have you been to?
Let’s see how much he likes to get out and about.
What’s the most useless skill you’ve got?
This is going to be funny.
Do you like to inspire people?
Or does he literally not care what others do?
How long have you been looking for love?
Kind of a personal question so it’s better to wait a while before asking it.
139. Do you believe in true love?
Is he going to give you the answer you crave? Or is he going to send you home in tears by declaring that “TRUE LOVE DOES NOT EXIST”?
Would you love to be famous?
Or does the idea of fame repel him?
And if he does want to be famous, what does he want to be famous for?
If you could remove a law, what would it be?
Ooooh basically, what crime does he wish he could get away with?
Let’s just hope his answer isn’t too scary!
What used to scare you that you now do all the time?
What have you been meaning to do forever but still not done?
And why hasn’t he done it yet?
What’s The Most You’ve Ever Spent On One Thing?
This question will give you a major insight into his spending habits. Does he splash out on frankly ridiculous things when he’s got too much cash in his pocket?
Or is he super frugal and the most expensive thing he’s ever bought is a microwave?
In which case – boring!
What do you prefer, experiences or possessions?
If you could have a celebrity friend, who would it be?
We’d go with The Rock.
What’s your favourite sitcom?
If you both love the same sitcom, just imagine how great it will be to watch together in bed. Aww. Cute.
Do you root for movie heroes or villains?
How important are your principles to you?
Or can they be swapped for others?
What Did You Used To Hate That You Now Love?
Let’s face it, we’ve all been wrong about something (except Beauty and Tips, of course).
There have been things we’ve been super suspicious of and even downright hated, only to then later try them and realise that, actually, we kinda over them!
This could be anything – food, alcoholic beverage, Leonardo Di Caprio!
Find out how open minded he is to change and admitting that he was wrong by asking him this question.
Do You Like To Read And If So, What Are Your Favourite Books?
Nope, not every guy likes to read. If you love to read but he never reads, you don’t need to hold it against him or judge him too fast, of course. There are lots of smart, interesting people who just never get the time to read, or who don’t get stimulated by a book.
On the other hand, if he loves to read, ask him what his favourite books are and hopefully it will inspire a riveting discussion.
What Do You Do In The Morning?
Is he a morning person? Does he have a morning routine?
Does he make breakfast and would he make you an amazing breakfast, too?
These are important questions that you need to know the answer to!
What’s the biggest mistake you’ve made?
Is he man enough to own up to his biggest blooper?
What does being a friend mean to you?
This question will reveal more about his values and give an insight into how he treats others.
Do you have any phobias?
Pray to God that he isn’t scared of spiders. Otherwise, you’ll need to move onto the next man who’ll get rid of spiders for you!
Do you mostly say “yes” or “no” to people?
How selfless or selfish is he? Does he value his time or is he always helping others?
Do you like shopping?
His answer to this question had better be a big fat “yes!!!”
Do you ever get angry?
It’s fine if he gets angry now and then, and it doesn’t mean he’s a total psycho.
On the other hand, if he answers “all the time” you should probably be a bit wary.
What’s the best decision you ever made?
Again, this is another great question that will get him to talk about himself and the things he’s done.
What’s the worst decision you’ve ever made?
Eek! Has he ever married the wrong person, for example?
What can a girl do to make you walk out on her immediately?
Just so you know!
What’s your perfect weekend?
We hope it isn’t burgers, beers, basketball and buddies.
If you won $1,000,000 how much would you give to charity?
Just watch him try to impress you with this one:
“I’d give half to charity because I’m such a nice guy.”
What sports do you like?
What would you do if he says he likes all the sports?
Do you have any weird habits?
Bad habits are one thing weird habits are just plain odd. Make sure you find out what they are!
Do you cry much?
And if so, how much? Please don’t say every day.
Do you sweat the small stuff?
Or does he take it all in his stride?
Do you think there should be more hours in a day?
And what would you do with those extra hours?
We’d all sleep, wouldn’t we?!
How important is football to you?
How much time do you spend on Facebook?
Imagine if he shames your FB habits by saying he doesn’t even have a Facebook?
Who is your celebrity crush?
Always a fun question.
Until he answers Joan Collins.
What makes you angrier than it really should?
It’s gotta be when the person in front of you suddenly stops walking.
What’s your favourite animal?
Let’s hope he’s an animal lover.
Imagine if he said “None.”
What’s the meanest thing you’ve ever done?
Let’s just hope he hasn’t been too mean.
Do you believe in ghosts?
If he literally goes pale and stares at you silently after you’ve asked this question, you know he’s had a horrifying experience with ghosts.
Do you judge people?
And if so, what does he judge them on?
When it comes to dating, do you have a type?
Most guys do – let’s find out what his type is.
Which song do you sing in the shower?
Come on, we know guys sings in the shower. We just wanna know what songs!
Do you want to die young or old?
Interesting insight into how he feels about growing old.
What’s your ideal date night?
Is he a restaurant man? Or does his date night involve taking his women to another city altogether?
Are you good at fixing things?
It’s important that you know how practical he is … or whether you’ll have to fix HIS car!
What’s the first thing you think of in the morning?
What do you think about homeless people?
What’s the most selfless thing you’ve ever done?
Find out how big his heart is.
What was your best year so far?
Which year does he look back on fondly, and why?
If you could be the same age forever, what would it be?
Gotta be 21, right?
Do you think taxes are too high or too low?
Oh, getting all political.
What would you do if someone was being racist on the bus?
Would he intervene or keep quiet?
What do you do when you come up against a problem?
Does he get angry and frustrated and call it quits? Or does he keep a level head and work out a solution?
His answer to this question will give you an insight into his temperament and how he deals with setbacks.
And let’s face it, no one really wants to date someone who can’t handle setbacks. It’s not what happens to us that matters – it’s how we respond to things that matters.
How do you react to compliments?
Different people react differently to compliments. Although you’d think everyone would be happy to be complimented, some people genuinely don’t know how to react – or they react badly.
For future reference, find out how he reacts to compliments.
What’s the worst thing a girl has ever done to you?
Has she lied to him, cheated on him … attacked him?
It’s a slightly nosy question and not necessary but it’s well worth asking if you two are to grow together.
Do you collect anything?
Now’s the moment he’s going to reveal his secret collection of teddy bears in his bedroom.
Hey, you asked for it!
What would you do with a million dollars?
This question will give you a better insight into what he’s like with money. Would he blow it all at once on something ridiculous? Would he invest it? Would he treat his mom to something nice?!
Do you like surprises?
Or do they annoy him?
If they annoy him, he sounds a bit miserable to us!
No offence if you like him.
What do you do to calm down?
Does he take long walks, perhaps?
Are you creative?
If you’re a creative person yourself, it isn’t essential that he’s creative too – but it can certainly help with compatibility.
Fellow creatives just “get” each other more than non-creatives do.
Find out if he’s a creative person, and if he is, ask what his creative outlet is.
Do you like to party?
Or is he happier with a cup of tea and Netflix?
Is he a party animal who stays out late at the weekends or does he prefer to cuddle up next to his girl in bed?
These are key questions.
Do you listen to your heart or your head?
This question will help you learn whether he’s impulsive and instinctive, or whether he’s rational and takes his time over his decisions.
Lots of guys let their hearts rule their heads, but does this mean they make the best decisions? It’s a big question.
What word describes you best?
This will give you a major insight into what he thinks is his most defining quality. Is he mr honest, mr ambitious, mr fun … or mr lazy?
Let’s just hope he isn’t mr football.
Are you open to marriage?
Again, like a number of questions on this list, this one isn’t a question you should be asking too soon. The timing has to be perfect. Ask it to soon and it will scare him off.
On the other hand, you also don’t want to ask it too late. If you do, you run the risk of getting too emotionally involved with a guy who ultimately doesn’t want what you want in the long run.
What’s the best book you’ve ever read?
Some guys don’t read at all, but surely all guys have read a book at some point in their lives.
Especially if he’s a keen reader, this is a good question to ask as the least it will do is inspire a discussion.
And maybe you’ll get an awesome book recommendation out of it!
What is your biggest strength?
Is it his courage or his ability to stay focused when things are going wrong around him?
Or perhaps it’s his listening skills or his knack for being able to communicate with everyone like a pro?
What is your biggest weakness?
Big question because it isn’t easy for men to even admit they have a weakness, let alone actually talk about it!
Get him to open up with this question and see how he really feels about himself. Does he fall in love too fast? Or maybe he gets stressed far too quickly?
If you could turn back time and do something again, what would it be?
Basically, what was SO fun that he would jump at the chance to do it all over again?
We’ve all had those winning life moments that we wish we could replay over and over again. Find out what his is and get him into a positive frame of mind as he jumps back in time.
Do you like roller coasters?
If he doesn’t, it’s game over, right?
Do you believe women deserve equal rights to men?
He must surely know there’s only one right answer to this if he wants to keep dating you.
Do you forgive easily?
Some forgive easily, others don’t.
Some, in fact, don’t forgive at all.
The problem with not forgiving is that we’re also punishing ourselves because we’re not allowing ourselves to move on.
Ask this question to find out how understanding he is that people make mistakes.
Because let’s face it, there’s going to come a time when you lose his football tickets or walk across the TV just as his team score a goal.
What’s your biggest pet peeve?
What can he not stand? What rubs him up so badly that he wants to tear his hair out?
Let’s just hope it isn’t girls who take too long to get ready.
What’s the most embarrassing thing you’ve ever done?
This should invite a funny answer!
The thing is, once he’s answered this, he’s definitely going to ask you the same question. So be prepared!!
What fictional character are you most like?
It’s an interesting question but there’s a chance he’s going to pick a character you’ve never heard of.
There’s also a slight chance he’s going to pick The Terminator or Bruce Willis’ character in Die Hard.
Hey, he’s a guy.
Imagine if he picks James Bond?
“ … Really?”
Do you believe in luck?
Or does he believe in fate?
Or does he believe in nothing at all?
Maybe he believes that we all create our own luck, good or bad?
Either way, it’s an interesting question that should inspire a pretty good discussion about how the choices we make impact who we are as people.
What would be your perfect career?
This gives you a huge insight into what he’d really love to do with his life. What is his dream job?
More to the point, why isn’t he doing his dream job right now?
Do you get jealous?
This is a key question that you can ask anytime. If he’s the jealous type who can’t bear the thought that another man could be looking at his goal let alone talking to her, you need to find out as soon as possible.
On the other hand, how would you feel if he says he literally never gets jealous at all? Surely we’d like our man to feel a bit jealous if we were hanging with another guy? Doesn’t it mean he really likes us and doesn’t want to lose us?
If you could live for a day as a woman, would you?
And what would he do as a woman?
Expect his answer to get a bit weird. We’ve warned you!
What’s the perfect night in for you?
Is he the kind of guy who wants to crack a bottle of wine out and chill to some movies with his girl?
Or does he prefer beer, buddies and baseball?
What does love mean to you?
This question will give you a huge insight into how compatible you guys are. What does love mean to him?
How important is it that your girlfriend challenges you?
Is he looking to be mentally challenged in a relationship? Or does he want a sycophant who’s going to agree with everything he says?
This question will give you an insight into how big his ego is, and whether or not he’s open to having his ideas and opinions challenged by women.
What’s the nicest thing someone has ever said to you?
When people say something super nice to us, we tend to remember it. Find out which compliment sticks out in his mind.
Then decide whether or not you’d agree with it!
We also have an article about 400 questions to get to know someone deeply, you can read it here.