400 Questions To Get To Know Someone Deeply
Talking to someone new that you think you kinda like? Want to learn more about them and get to know them deeply? The best way to do that is by asking them questions.
One snag: The questions we often ask are a bit lame. We ask them, “So! If you could go anywhere right now, where would it be?”
Cliche alert 101!
And then when we’ve asked 2 questions and literally can’t think of anymore, we ask “So! … How was your day?”
It’s a nice question to ask someone, but it doesn’t give us an insight into who they are and whether or not we could actually like this person.
At Beauty and Tips, we put a lot of value into relationships building. We think that asking questions and actually listening to the answers is the best way to make new friends, partners and more. Let’s take a look at the 400 questions you can ask to get to know someone deeply.
If you’re currently involved in the dating scene and actively looking to date and get to know someone, the topic of dating is kinda important.
There are plenty of questions to ask, ranging from his dating preferences to what he likes to do on a first date, and they’ll give you a better insight into how you both feel about the weird and wonderful world of dating in general.
Would you date someone who used drugs, even soft ones?
It’s nice to know how someone you might be dating feels about drugs.
How important is it that someone shares your sense of humour?
Is intelligence a big factor you take into consideration when dating someone?
It most likely is, but who knows?
Are you a serial dater? Or are you more selective and pick your dates wisely?
Which answer would you prefer here?
Have you ever ended a relationship or has it always been the other person who called it quits?
This is an interesting question to ask because it gives you an insight into their tolerance levels. Are they willing to give things “another chance” to see how things pan out? Or do they nip things in the bud early and move on?
Are you a romantic person?
See above. Who wants to date someone who isn’t romantic?
“Nah, I’m not romantic. In the slightest.”
Would you date someone who was lazy?
If they would, it probably gives you an insight into how lazy they are.
Do you need someone in your life right now, or are you content enough by yourself?
Do they have a void that they want you to fill? Some people can’t cope with that kind of pressure, so it’s a good idea to find out what their needs are.
How do you prefer to meet new people? Online or in real life?
Maybe they’ve grown accustomed to this online dating thing, or maybe they’re still a traditionalist at heart.
Is chemistry important to you on a date?
Do looks come before personality or vice versa?
They’ll probably say that a good personality always wins.
When did you have your first kiss?
This could get them to tell a hilarious story.
Has online dating changed dating for the better or the worse?
It’s an interesting question that should inspire a bit of discussion.
Would it bother you if your partner went away for a few days without you?
Or do they have to be with their partner at all times?
How important is an active sex life in a relationship? Do you need it a few times a week?
Two people who get together generally need to be on the level where sex is concerned.
Is it okay to flirt with other people when you’re in a relationship?
If their answer to this is different from what yours would be, you might need to have a talk.
What’s your idea of the perfect first date?
Oh, this is a lovely question to ask! Let’s see how romantic they are!
Has there ever been someone you dated who you thought you could marry?
Or have they still never found “the one”?
Would you date someone who didn’t have a job?
Or do they need to be with someone who’s financially stable and “got it together”? Some people find it hard to shoulder all the financial burdens in a relationship by themselves.
Do very attractive people make you nervous?
Or are they naturally confident and comfortable around anyone? It’d be cool if they are.
Do you tend to date more than one person at the same time, or is your focus always on just one person?
Don’t ask this until you’ve been dating a while because it might put them off. But later on down the line it’s always good to know where you stand.
If the person you’re seeing was dating someone else at the same time as you, would you prefer to know?
See above. Transparency is good when you’re dating someone as it prevents misunderstandings and potential conflict.
What would be a dating deal breaker for you?
Find out what would make them stop dating you!
How important is chemistry on a first date? If it isn’t there, would you be willing to give it a second chance?
Most people wouldn’t but it’ll still be interesting to hear their answer so that you know where you stand.
Could you date someone who you disagree with politically?
This could be where it all comes to an end!
Do you enjoy debating politics on a first date?
Or do they prefer to chill and take it easy?
Is it a case of brains before beauty, or is it the other way round? Or do you need both?
Surely they need both – but, hey, we’re not judging!
When was the last time you got really drunk on a night out and came home late?
If it was literally “last night … and the night before … AND the night before that” you might be in trouble.
Where do you think is the best place to meet people of the opposite sex?
What is love to you?
It would be interesting to learn what their idea of love is.
Do you believe in true love?
Imagine if they said “no.” OMG.
Would you date someone just because they were rich?
Find out how superficial they are.
Do you like to take the lead in a relationship?
Or do they prefer to follow?
What quality above all others do you look for in a woman?
And do you have this quality?
Are you insecure in relationships?
It’s important that you know the answer to this before all their insecurities come spilling out.
When was the last good date you had?
And why didn’t it work out?
Do you like meeting new people?
Or do they hate people?
What do you consider to be a good first date?
Find out what you need to do to make this a success!
And what do you consider to be a bad first date?
Find out what you need to do to make this a disaster!
Do you get nervous before a first date?
If they say “hell no!” they’re literally not human.
Do you kiss on a first date?
Do you always text after a first date, even if it didn’t go well?
Or do they leave you to wonder what the heck happened and cry in existential misery by yourself?
How many dates do you think two people should have before they’re officially a couple?
Are they the kind of person who wait months before saying something is official, or do they like to move faster than that?
What are you looking for in your next relationship? Are you just looking for fun or do you want something more serious?
It’s really important that you find out if they’re looking for the same thing that you are.
Do you take chances on a person you fancy in a bar, or does the fear of rejection get the better of you?
Find out how confident they are in their chat-up lines.
Ah, politics. Let’s face it, politics are everywhere. We might hate it, but we can’t always ignore it.
When it comes to dating, politics are a sore subject. Is it dating etiquette to avoid politics on a first date? Or is it really important that we uncover someones political affiliations as soon as possible so we can make a better decision about them before we waste our time?
Be careful though – political discussions always get tense.
What do you think about guns?
Big, loaded question.
Are wars necessary?
See above. Like any of these political questions, only ask it if you’re ready for a big old debate.
Do you have a political affiliation?
Find out if it’s the same as yours.
Should cannabis be legal?
This could spark an interesting debate. Prepare for an argument!
What do you think about abortion?
This is where things might get heated if you both disagree …
Do you believe that we all have a duty to uphold the law?
Interesting question that could spark a debate.
What do you think of the death penalty?
How important is politics in your life?
For some people, politics IS life.
Do you respect everyone’s right to an opinion or do you think they should all agree with you?
It’d take a lot of balls for them to say that everyone should agree with them.
Where do you go for the latest political news stories? Which websites and media outlets?
Find out if they use websites and media outlets that you vehemently oppose.
Could you break up with someone if your political views were too different?
What do you think of homeless people?
When you get into a relationship with someone, it’s important that you like their personality!
The two of you don’t need to have matching personalities per say, but they have to be pretty similar.
Movies like Along Came Polly have, of course, show us that two very different personality types can complement one another and encourage each other to change and grow.
Are you an extrovert or an introvert?
Find out what personality type they are, and if it matches with yours.
Are you an exhibitionist?
Are you a kind person?
Or are they just kind to the people they know?
Do you try to live each day as though it’s your last?
Or are they more reserved?
Are you charitable?
Are you a confident person?
Confidence is pretty important when we’re looking for a life partner.
Are you a narcissist?
Would you keep dating them if they were a narcissist?
To be fair, if you feel the need to ask this question, it probably means that you’ve already got your answer.
Are you an optimist or a pessimist?
It’s important to know if you’re dating a positive or a negative person.
Are you an animal lover?
Especially if you are, this is a key question.
Do you prefer pets to people?
Of course they do!
Are you a vegetarian or vegan?
Are their lifestyle choices compatible with yours?
Are you a confident person?
This is a key question.
Do you like to host parties, or do you prefer being a guest who can hide in the background?
A good question that should you give an insight into how compatible they are with you.
What makes you feel safe?
Do you like hugs?
Imagine if they said No.
Are you of the motto “live for today for tomorrow we die” or are you more reserved?
Ask this question to discover whether they like to take big risks or not.
If there’s something I like that you’ve never tried before, would you be willing to give it a go?
This is a good question. Are they going to be brave enough to try a hobby of yours? And would you be disappointed if they’re not brave enough?
What do you do when you feel down?
How do they react when something has upset them?
Are you an angry person?
Before you get in too deep with someone, it might be a good idea to find out how temperamental they are.
Do social events make you anxious or do you like forward to them?
If they hate social events and you love them, is this going to work?
How often do you go to clubs?
We all like a club now and then, no?
Do you prefer nights in or nights out?
Again, a key question that will highlight how compatible they are with you.
Do you like to be seen out and about in public or do you prefer to keep yourself to yourself?
Are they a homebody basically?
Do you like to dance?
If you love to dance, this is a very important question.
How important is having space to you?
Space is important in any relationship – but is it important to them?
Could you live with someone else, or would you rather live alone?
How far can a relationship really go if they don’t want to live with you?
Do you believe that money brings happiness?
Let’s see how attached they are to material things.
Digging up their past must be done carefully – not forcefully with a shovel. Tread softly with these some of these questions and only ask them when the time is right.
“Should I even go snooping into their past at all?”
It’s not snooping – it’s being vigilante. The past can shape who we are today and it’s important that he hasn’t got any skeletons in his closet that leap out and surprise you at a later date. If there is something from this past that needs airing – be it an ex partner or a prison spell – now’s the time to give him the chance to air it.
Have you ever had an addiction that’s needed to be treated?
It’s important that you know their past.
Are there any ex partners that are still in your life?
It’s worth finding out who they still talk to from past relationships – and how much of a threat these people are to you.
Do you still have feelings for any ex partners?
Have you ever been to prison?
It’s important that you know key details like this about their past.
Is there anyone from your past who you’ve never forgiven?
Find out if there is something bitter from their past that’s lingering. If there’s something they haven’t forgiven, it could be affecting their day to day life.
Have you ever been in love?
Or have they never found “the one.”
When was the last time you cried during a movie?
A guy might not like to admit that he ever cried during a movie but it’s still a question worth asking!
What’s the most expensive item you’ve ever bought?
Find out how lavish he can really be with his money.
Have you ever been in therapy?
Only ask this when the time and context is right. It’s not a random question.
Have you ever gone teetotal? What was that like?
And why did he decide to try it?
Have you ever been on a road trip?
And if he has, let him open up to you about it. It could make for a great story!
Have you ever nearly died?
Bet you’d love to know their story!
What’s the best job you’ve ever had?
Get him to reminisce about some good times!
Are you over all your ex partners?
Ask this question when you’ve already been talking about ex partners. Don’t randomly bring it up!
Is there anything from your past that haunts you?
Careful – this question could make them emotional.
Are you a nostalgic person?
Would you say that you live in the past, the present or the future?
Would you say that our past shapes who we are?
Have you ever been bullied?
And have you ever bullied someone else? If you have, how does that make you feel now?
How old were you when you had your first girlfriend?
Do you try to look forward at all times?
What’s the most hurt you’ve ever felt?
What’s the biggest setback you’ve ever encountered? And how did you work to overcome it?
Family is a really important topic, especially if you’re very family oriented. It’s important that you learn what his relationship is like with his family, including whether or not he has any plans to start one of his own.
Do you want kids?
It’s important to have these kinds of talks .
How important is family to you?
If Family is important to you, you might need to find out if it’s important to them, too.
Does family come before anything else?
Do you like children?
Ha! Imagine if they didn’t but you really do?
Is your family rich, poor or okay financially?
Is this an essential question?
Well, it kinda is.
Think about it – if their family is poor, they might also be burdened with the financial fallout. Often, you’ll find someone bailing out their family who are struggling to get it together financially. Is that something you could cope with?
How important is it that your partners family and yours get along?
Or do they not mind a good old family feud?
Has any of your family broken the law in a pretty big way?
And if so, what did they do? Is the family over it now?
Are you a family-oriented person? If not, why not?
For some of us, it’s really important that our partner is family oriented. After all, we want to visit their mom and dad, and raise our future kids in a proper family.
Do you love your mom?
All boys love their mom, right?
When did you first move out of your parents house?
Or do they still live there omg?
How The Feel About Themselves
How he feels about himself will give you a greater understanding about what he’s really like as a person. Is he secure or insecure? Does he like himself or loathe himself?
What’s your best physical feature?
Find out how they feel about their appearance – and see if you agree with it!
What do you like the most about yourself?
Guys like talking about themselves, after all.
What do you hate the most about yourself?
Okay, guys like to talk about themselves, but they probably don’t like talking about their weak points. Which is why you need to get them to open up at some point with a question like this.
Do you take pride in your appearance?
Would you date someone who didn’t?
How important is fashion in your life?
Fun question! Find out if you’re dating a fashionista or a scruff.
Do you like to look good?
Or do they not care?
Do you buy branded clothing?
How much money do you spend on clothes?
It’s good to know if their relationship with money is anything like yours or not.
Are you happy with your appearance?
Most people aren’t, but it will get them talking.
If there’s one thing you could change about your appearance, what would it be?
Bet he wants to look like Jake Gyllenhaal.
If there’s a movie star you wish you looked like, who would it be?
See above! Ha!
Who would play you in a movie?
Jake again …
The Philosophical Stuff
It’s 11pm. The two of you have polished off a few glasses of wine. The night is theoretically coming to an end but you’ve just noticed that he has a collection of Descartes’ best works on his shelves.
So now it’s time to break out the philosophical questions!
Have you written your will?
Bit morbid but an interesting question.
Do you believe in God?
Would it matter to you if their beliefs were incompatible with your?
Do you wish there was an afterlife or would you rather prefer this was all there is and will be?
Now you’re getting very deep and philosophical …
Are you scared of getting old?
The two of you can console each other about ageing and grey hairs etc.
Do you worry that one day you won’t look as good as you do now?
OMG do you want to make them cry?
What is your life philosophy?
A person’s life philosophy is pretty much what dictates their every subsequent decision. So it’s kinda important.
What are your thoughts on the afterlife? Do you think it exists?
This could lead to a pretty cool debate and inspire some in-depth discussion.
What are your thoughts on religion? Are you of the “live and let live” philosophy, or do you think all religions are bad?
See above. Things could get tense here, though!
Does dying scare you?
This is a deep question that should be asked only when the time and context is right.
Health and Wellbeing
Health and wellbeing is kinda important – to some people.
If someone cares about their health and wellbeing, as well as that of their partner, it means that they’re planning on being in this in the long term.
If, on the other hand, they take much more of a “take it or leave it” attitude to health and wellbeing, you have to question how much they really care about anything, right?
Would you say you’re healthy?
How important is health to you?
Is it your main priority, bruh?
How important is it that your partner is healthy?
Surely it’s essential? Or are they gonna be a “I don’t really care about you” type?
Do you look after yourself?
If you look after yourself, this is a pretty key question?
Do you go to the gym?
And if they don’t, do they at least exercise at home?
Do you eat well?
Or do they eat so much junk that they’re literally making themselves sick?
Do you meditate?
Meditation is a great way to clear our mind. It allows us the chance to focus better and eliminate the small stuff that’s clogging our brains up. If they meditate, you can be pretty sure that they’re healthy of both mind and body.
Are you a spiritual person?
And if so, what does spirituality even mean to them?
Do you smoke?
If you don’t know the answer to this already, you might want to get asking it.
How big a part in your life does alcohol play?
Do they drink to be social? Or are they a lone drinker who drinks at home each night? A persons relationship with alcohol can tell you a lot about them.
What would you do if you thought you were ill?
Would they go to the doctor? Or do they not care?
Finances – like politics – can be a bit of a minefield. Let’s face it, our own personal finances are, well, personal. But if you feel that your relationship with him is starting to progress, you need to broach the subject of finances eventually.
Why? Well, you need to know how financially stable they are. It’s key to the long term success of any relationship.
How much do you have in savings?
It’s important that you find out how financially stable someone is before you get into a long term relationship with them.
Do you spend more than you save? Or do you save more than you spend?
Are you careful with money?
Or do they blow their WHOLE pay-check within 24 hours?
Are you doing well financially? If not, why do you think that is?
It’s a loaded question. If they’re doing well or badly, this question will give you an insight into how good they are at making decisions.
Do you like spending money? Or are you more of a saver?
Spending is fun, but sensible people – the kind you can see yourself having a long-term relationship with – are very good at saving money, too.
Do you have any investments?
The thing is, even if he does have investments, that doesn’t necessarily make him smart. After all, they could be very bad investments!
Do you gamble?
Gambling isn’t bad per say – but it depends how much someone gambles.
How important is money to you?
Do they place a lot of value in money?
Where does work fit into your life? Is it just something you do because you have to pay the bills, or do you happen to love it?
One thing you’ll need to consider is if you could date a potential workaholic.
Because who doesn’t love a good holiday?!
If you’re going to start dating someone – short or long term – you need to agree on holidays right from the start. If you’re the kind of person who wants to go on safari or see museums, while he just wants to get mega drunk, you’re hardly going to have the holiday of a lifetime, are you?
How many holidays a year do you like to have?
Are they the kind of person who practically lives for holidays?
How important is it to you that you have at least one holiday a year?
Do they need to get away or do they not mind if they have to stay at home? This is a pretty key question if holidays are an essential part of your year.
What kind of holiday do you prefer? Safari? Beach? Culture?
Find out if the type of holiday they prefer is the same as yours.
Do you crave lots of sunshine or do you prefer cold weather?
Ask this question to see if you both like the same seasons – or if you’ll be miserable in the winter and they’ll be loving life!
What’s the best place you’ve ever visited?
This question will invite them to tell you an awesome story of one of the best times in their life.
Do you like to travel?
Good question if travelling is one of your hobbies.
How often do you travel?
Do you prefer to travel alone, or with other people, such as a partner?
Kinda important that you find out now if they’re the sort of person who travels alone a lot out of choice.
How much money do you spend on holidays?
Do they break the bank each year for a holiday?
Do you like to get drunk on holidays? Or are you a chance to kick back, relax and take in a new city and a new atmosphere?
Find out what they like to do on holiday so that there are no nasty surprises when you go away with them.
Do you see work as something just to help pay for holidays? Or is your job so good that it’s almost like you’re on holiday all the time?
Some people happen to love work so much that they don’t even think about holidays. Find out if you have a workaholic on your hands.
Are there any religious holidays you celebrate?
Ask this question to find out if there are any religious holidays you’ll be expected to start celebrating if you get with them.
Do you celebrate your birthday or is it not so important to you anymore?
The funny thing about birthdays is that they can dwindle in importance as we get older.
If you could live anywhere, where would it be?
It would be nice to know if their dream destination is the same as yours.
How important is music in your life?
Do they spend a lot of time and money on it?
What virtues do you like the most?
What’s your favourite season?
Wouldn’t it be nice to meet someone who loves winter just as much as you do?
Can you cook?
Wouldn’t it be nice to meet someone who can cook for you?!
Are you happy with where you are in life right now? Or do you want more?
This is a pretty deep question that should elicit a well-thought out response.
What was your childhood like?
Oh, you can’t beat a good childhood question!
If you could go back to any time in your life, when would it be and why?
Taking them on a trip down memory lane is a good idea because it will make them feel all warm and fuzzy inside.
Do you have a current passport?
Kinda important if you wanted to take off to Italy with them next week.
Has anyone hurt you in the past?
Make sure to ask this at the right time. Otherwise, you’re just opening up wounds unncessarily.
Have you hurt anyone in the past?
Do you have a best friend?
Aww, get them to talk about their bestie and all the adventures they’ve been on together!s
How important are friends in your life?
Hopefully they’ll be pretty important, right?
What are your biggest priorities right now?
Aside from you, of course.
If you could only do one thing for a day, what would it be?
Hopefully not “sit around and watch sports with nachos.”
How important is it that your friends and your partner get along?
For a lot of people, it’s usually very important.
What would make you instantly break up with someone?
What one thing would they not forgive? Just so you know!
Are you always there for your friends?
Or are they the kind of person who goes missing when people need them the most?
Do you have time for strangers in need?
Please say “yes.”
Or you a movie or a TV show person?
It’s important to know if you’ll be watching movie marathons or TV box sets with this person.
If you could be someone else for the rest of your life, would you?
Imagine if they said “I want to be you.” Awkward.
Do you like yourself?
This question could open up a whole can of worms, so be prepared.
Do you believe that it’s okay to make mistakes as long as we learn from them?
Or do they believe that mistakes are a sign of failure?
Do you give any of your earnings to charity?
How important is it that your partner is kind and considerate?
Or do they not care about that sort of thing?
Would you be willing to commit a crime for someone you loved?
Now, this is interesting.
How tolerant are you?
Or does their patience soon run thin?
Are you open minded?
Or do they think that everyone should subscribe to their world view? Are they open for trying new things?
Do you forgive easily?
Or does it take a long time for them to move on from something?
What’s the worst thing someone could do to you that you wouldn’t – under any circumstances – forgive?
Apart from, you know, murder.
Have you ever broken the law but got away with it?
Ha! Cheeky question that could provoke a funny response.
What do you value the most in a partner?
What values do they like the most in a woman? Kindness, empathy, compassion?
Do you believe in always telling the truth? Or are there occasions when it’s okay to lie?
It’ll be interesting to see what their answer is to this. Is it ever okay to tell a lie? Really?
Have you ever been arrested but not sent to jail?
Find out more about their past with this one.
Have you ever been in a fight?
Or are they more of a lover than a fighter?
What’s your biggest regret in life?
This could get emotional, so be prepared!
Have you ever fought with your best friend?
Have you ever hit a woman?
OMG see above.
Would you hit a woman in self-defence?
And how would you feel if they said yes?
When was the last time you lost your temper?
Find out how often they lose their rag.
What makes you angry more than anything else?
This could be anything, from politics to people slowing down in the street.
Do you believe in killing someone for a good reason – for example, if they’ve hurt your family?
Bit morbid but worthy question that will give you an insight to their principles.
How important is revenge? Or should we keep calm and let bygone’s be bygone’s?
Do you watch the news?
Or do they prefer to let the world take care of itself?
Are you a culture vulture?
Do they like to visit galleries and museums?
Do you read?
Or have they never read a book in their life?
Do you like to learn?
Or does learning belong in school?
Did you go to college?
Or is he self-taught?
Do you have a degree?
Find out how educated they are.
Do you think college education is just a waste of time?
Some people think it’s a waste of time and money.
How important is it that your partner is smart?
And then make sure that they know you’re super smart.
Are you well-read and knowledgeable, or are you more street-smart?
Do you like to have stimulating, intellectual conversations?
How amazing would it be to find a partner who does?
What’s your idea of fun?
Let’s hope it’s the same as yours!
What do you like to do at weekends? Do you prefer to lounge around the house all day, or do you like to make the most of your time off work and do stuff?
This is a lifestyle question. If what they like to do at the weekend is very different to what you like to do, this might not work out.
Are you the type of person who could spend all day in bed with your partner filling out crossword puzzles?
It’d be awesome if they are, right?
How good are you at communicating?
Communication is the bedrock of all good relationships. Make sure that they’re good at communicating before you get with them.
What hobbies do you have?
A fun question that will give you an insight into what they do in their day to day lives when they’re not at work.
Is it important that your partner has a few hobbies?
Or would they rather you sat around and did nothing?
Do you like to share your hobbies with your partner or do you like to keep them separate?
This will give you a good idea as to whether or not they’re going to involve you in what they do or keep you totally separate.
How much money do your hobbies cost?
Find out how much of their wage is going on their hobbies. Maybe they have an expensive hobby – such as go-karting – or maybe they have a really inexpensive one, such as reading.
How much time do you spend on your hobbies, and would you consider spending less time on them if you entered a new relationship?
It’s important that you find out as soon as possible if you’re dating someone whose whole life is consumed by their hobbies. And if it is, are they willing to cut down on their hobbies if they entered into a new relationship?
How important is food in your life?
Let’s hope it’s very important, huh? 😀
Do you eat well or do you have lots of bad habits?
By bad habits, you mean junk food, cakes and sugar.
Can you cook?
Cooking is a pretty useful life skill to have. Maybe it says a lot about someone when they can or can’t cook?
Is it okay to eat junk food now and then?
If they say “yes” you just know they eat junk food a lot 😀
Do you consume a lot of sugar?
It’s important that you find out what their relationship with sugar is. Anyone who consumes an excess amount is putting themselves at risk of developing a long term debilitating disease, such as diabetes.
Are you a health freak when it comes to food?
And will they expect you to be a health freak, too?
Could you date someone who had different eating preferences and values to you – for example, a meat eater, vegetarian or vegan?
This will give you an insight into their tolerance levels.
Do you like to eat out often?
Find out if they’ll be treating you to lots of restaurant dates, or if the two of you will be ordering takeout food all the time.
Would you go to a restaurant on a first date?
What cuisine is your favourite?
Wouldn’t it be cool if you both liked the same thing?
Do you share food? Or are you like Joey from Friends in that you keep all your food to yourself?
Find out how selfish they are at the dinner table.
Do you think women should cook and men should just eat?
This question will give you a better insight into whether they are a traditionalist or a progressive.
What do you think of vegetarianism and veganism?
Careful – things could get nasty here!
How much money do you spend on food a week?
Ask this question to gain a better insight into their finances and where their cash is going. Food is important but find out if they’re not overspending.
Are you a morning person or are you more of a night owl?
This is a key question to ask if you’re a morning person or more of a night owl yourself. It’s hardly going to work if they go to bed at 10pm while you’re just coming alive at that point.
Are you spontaneous or do you have to plan everything in advance?
Find out how calculated – or how much of a “control freak” – they are.
If I gave you a million dollars right now, what would you do with it?
This question will give you an insight into what’s important to them. Will they blow it all immediately on a yacht? Or will they make smart decisions?
Who is your favourite person in the whole world?
Aww find out who matters to them more than anyone else. It could be their mum, their dad – or you?! OMG.
Are you an affectionate person?
If you like affection from a partner, this is a pretty important question to be asking.
Do you open up easily to people or does it take you some time?
This question will give you some insight into the reasons why they’ve not opened up to you yet – if that’s the case!
Are you a trustful person?
Trust is so important in any long-term relationship. If someone isn’t trustful, there’s always a reason and it goes back to their past.
Have you ever been in love?
Most people have, and it could help the two of you bond if you talk about past relationships that, for one reason or another, didn’t work out.
What makes you happier more than anything else?
Find out what this is and then, at a later date when you want to lift their mood, you can do what makes them happy!
What’s your greatest strength?
Learn more about how they feel about themselves with this question.
What’s your greatest weakness?
Do you enjoy making other people happy?
Imagine if they didn’t?
How do you react when something has annoyed you? Do you get angry? Or do you take the time to cool down before reacting?
This is a key question because there are arguments in any relationship, and there will be times when they’ll get annoyed around you. Find out how they’ll react in such situations.
Would you date someone who’s really messy?
Or do they prefer people to neat, tidy and organised all the time?
Do you like sports?
And if they do, how important are sports to them? Do they watch them ALL the time?
How important is it that your partner gives you space?
There’s probably only one answer they can surely give to this question: “very important.”
What do you think of feminism?
This is a key question if feminism is important to you.
What’s your relationship like with your parents? Do you see them often?
It’s always a good sign if someone’s relationship with their parents is strong. If it isn’t, perhaps you could find out why. There’s usually a good reason.
What makes you feel insecure?
Find out what – if anything – makes them less confidence.
And what makes you feel secure?
Find out what – if anything – makes them gain confidence.
What’s your biggest turn on?
Just so you know.
What’s your biggest turn off?
If you could reincarnate as the opposite sex, would you?
It’s a fun question, but as they expand on it their answer could get interesting.
Are you an anxious person?
If someone is an anxious person, it’s really important that you find this out as soon as possible so that you don’t do anything that could trigger their anxiety.
Have you ever been on medication for mental health problems?
It’s not the most light-hearted question ever, but it’s still a key question to ask as you learn more about them and their past.
Do you think depression is a state of mind or a genuine illness?
It’s a provocative question that could inspire a very provocative answer.
Are you into personal development and self improvement?
It’s always a good sign when someone is into improving and bettering themselves.
How important is it to you that your partner is fit and healthy?
If it’s important, it shows that they care about you and your wellbeing.
What was the last good book you read?
Perhaps they can give you a recommendation and then you can both discuss it?
Do you still think about your ex partner?
It’s a good idea to find out if the person you’re dating is still hung up on someone from their past. If they are, should they really be dating you?
Have you ever lived with someone? What was it like?
This could fetch up some interesting anecdotes, but they might also say “yeah I have … never again!”
Have you ever lived abroad?
If they have, get them to tell you some cool stories!
What’s something that makes you feel really nervous?
Or do they have nerves of steel and literally never ever get nervous about anything?
When you’re in a relationship, does your partner always come first, no matter what?
It’s all about priorities. If you’re going to be down in the pecking order – below football and video games – it’s not a good sign.
Have you ever loved someone so much that you’ve thought “I could die for them”?
How do you divide labour in the home?
This question will give you a major insight into what life will be like if you move in with them. Will they be expecting you to do all the work at home, or will it be shared out fairly?
What’s your idea of equality?
Are they loving the fact that women are treated almost as equals now? Or does it bother them?
What do you think of Donald Trump?
Do politics even matter?
“Do politics even matter, bruh?”
What’s your biggest passion in life at the moment?
Find out what motivates them more than anything else right now.
And let’s hope the answer isn’t “dating.”
If you were to die tomorrow, would you say that you’ve had a good life?
This question will give you a massive insight into whether they’re a positive or a negative person. It’s all about perception. If they say they’ve had a rubbish life, you can be sure that’s largely down to their mindset. Remember, we pick and choose highlights and lowlights from our past and we can either focus on the good or the bad.
How do you want people to remember you? Say it in one word.
What scares you the most?
All guys – even if they won’t admit it at first – are scared of something. Get him to open up about what scares him the most – even if it’s spiders!
What makes you sadder more than anything else?
Find out where his emotional buttons lie. What makes his heart weep? Is it animal cruelty? A sad film?
Would you date someone of a different race to you?
This is a potentially provocative question but it’s well worth asking if you’re a little unsure about certain beliefs that he has.
Do you like texting and calling your partner often, or do you prefer to catch up in person?
Some people like to text a lot, while other people prefer to just catch up in person. It’s important that you find out what they prefer as soon as possible so that you know what each other’s expectations are. If they’re texting you all the time and you’re not comfortable with that, you need to let them know.
Would you describe yourself as a needy person or are you quite independent?
If you can’t deal with needy people, this is probably a question you need to be asking as soon as possible.
Are you a jealous person?
If jealousy is also something you can’t deal with, air this question as soon as you can.
Do you like to make other people happy?
Making people happy can be seen as a good thing, but if it’s literally someone’s mission in life, it usually means they have some issues of their own that need resolving.
Do people tell you that you’ve had a positive effect on their lives?
Aww, wouldn’t it be awesome if you found out that you were seeing someone who had a positive effect on peoples lives?
Do you like to get out and about often or are you more of a homebody?
This is a good question to ask so that you can see if the two of you are compatible “socially”.
What is your idea of a relaxing day where you do “nothing”?
Let’s hope it’s the same as yours!
Or maybe they don’t like to have days where they do “nothing”?
Do you like art?
It’s probably only a question if you’re into art yourself. Otherwise, you can leave it out.
How important is it that your next partner shares the same interests as you?
Some people think it’s super important, while others prefer to keep hobbies separate. Hey, each to their own, right?
Where do you see yourself in 5 years time?
This is a pretty intense question that will have them reflecting. Do they even have a 5 year plan? If you’re the top of person who likes to plan ahead and they’re not, it doesn’t mean that you’re incompatible, of course.
Are you where you wanted to be 5 years ago?
This is another solid question that should see them pause for a bit of reflection.
Do you like to set goals or do you prefer to go with the flow?
Are they a goal setter, or are they very much an “what will be will be” person.
Are you an ambitious, driven person?
Or are they content to – to put it politely – remain average?
How important is it to you that your partner is ambitious?
If they’re an ambitious person themselves, it’s likely that they’ll want the same drive in their partner.
Would it bother you if your partner was making more money than you and had a better job?
Ha, good question. A lot of men might be bothered by this – but some definitely won’t be.
Have you ever considered giving up your career to go and travel the world for a year (or longer)?
Most people have – but are most people willing to take that risk?
Would you ever change career again?
Or are they now settled? And if they would change career, do they have anything in mind?
If you were to start your own business, do you have any idea what it might be?
Many of us think we’ve got at least one business idea in us. Find out how original, creative and inspiring their idea is!
What was the last good deed you did, and why did you do it?
Find out what charity means to them? Did they help an old lady across the road, give money to homeless people?
Are you looking for love?
What are they in this for?
What’s your biggest regret?
This question can open up old wounds but it’s a good way to get them talking.
What motivates you to get out of bed in the morning?
What is the one thing that’s driving them forward at the moment?
Are you an active doer who makes things happen, or do you wait for life to happen to you?
This is an important question to ask in order to see how compatible they are with you. If you’re a doer, it’s going to be hard to date a passive person.
What does romance mean to you?
Is it a candlelit dinner?
Or is it sharing their X-box game with you?
What’s the best compliment you’ve ever received?
Most often, we remember what the best compliments we’ve ever received are. Find out theirs.
What do you get complimented on the most?
This will give you an insight into their real personality. If someone is always telling them they’re a good listener, it means that they’re a good listener.
Do you like to give out compliments often, or are they things that need to be earned?
Are they the kind of person who’s going to be complimenting you all the time? Or will you need to work hard for those? 😀
How would you and your partner cope with stress in a relationship? How would you handle it together?
This is a really good relationship question that gives you a little insight into how things would look if the two of you got together in the long term.
Have you ever been in debt? If so, how did you get out of it?
If they got out of debt, that’s really resourceful of them. Find out how they did it.
Do you like children?
If you want children but they’re not even child-friendly, this could be a massive deal breaker.
Are you a cat or a dog person?
Most guys are dog people. Let’s see if it turns out that he’s actually a crazy cat man!
How do you deal with fights in a relationship? What’s your method of diffusing the situation before it gets out of hand?
This question will give you a glimpse into what life would be like with him. All couples fight. How would the two of you defuse things? What is his method? Does he have one?
Would you expect your partner to make changes in their life to suit you?
It’s important that you find out as soon as possible that he expects you to make changes to suit him.
Have you ever had to make changes for someone? How did you deal with that?
Let’s see how flexible, selfless – or selfish – he is.
What is your relationship with money? Do you like it, or do you take a “money isn’t everything” attitude?
For some, money isn’t everything. Others, on the other hand, know that they need to make more money to live a good life. Find out how he really feels about money.
Do you like to be alone sometimes, even when you’re in a relationship with someone?
Or does he need you to be by his side at all times?
Are you an open or a closed book?
In other words, will he be sharing everything with you or keeping some things a secret?
If there is someone from your past who you would love to see again, who is it and why?
Aww, who are they missing?
Whoever it is, encourage them to get in touch with that person!
What’s your biggest fear about the future?
Find out what’s on their mind about the future – and then see if you can help allay those fears.
What’s the longest relationship you’ve been in?
If their longest relationship was less than 6 months, it can be a sign that they’ve never had the emotional maturity needed to deal with a long-term, committed relationship. And that can be a bad sign.
Are you open to marriage?
If you are, you need to ask this question before it’s a bit too late.
Do you enjoy being alone, or is it something you try to avoid as much as you can?
Alone time is important for a lot of people, but some people just don’t like it. If you love alone time but they don’t, you need to make it clear that they’ll need to respect your desire to be by yourself from time to time.
Who is your biggest hero?
Their hero will give you an insight into who they are as a person, and what they aspire to be.
Who has had the biggest impact on your life? And why?
See above. To find out more about a person, take a look at their heroes and the people who have had the biggest impact on them.
Who is most important to you right now?
It would be way too cute if it was you.
What do people notice first about you (apart from the way you look)?
It’ll be interesting to find out how others perceive them. What is it that people always notice first about them?
What’s your fondest memory?
What do they remember from their past that makes them smile? Ask them this question to elicit happy emotions within them.
What do you think the future holds for mankind? Are we heading in a good or bad direction?
“I think we’re all doomed.”
What would disgust you if a potential partner did it?
Just so you know.
What bad habits do you have?
Let’s face it, he probably snores.
Or leaves the toilet seat up.
Or forgets to flush.
Do you cry often? If so – or if not – when was the last time you cried?
Guys generally don’t cry often, and if they do it’s usually always sports-related.
Apart from the rent and bills, what do you spend money on the most?
This could make for some pretty interesting answers.
How much money do you need to make/having in savings before you can feel comfortable?
And what number makes him feel very uncomfortable?
What one essential quality must a partner have?
Let’s hope you have it!
What could make you jealous (even if you are not a typically jealous person)?
Come on, there has to be SOMETHING that makes even the most un-jealous person on the planet jealous.
What’s more important to you: That a partner is sexy or has a good sense of humour?
Oh, this is a good question! Most guys will probably choose a wicked sense of humour, though.
Name an occasion in the past when you felt really vulnerable
Let him open up to you here – but make sure the timing is right. Don’t ask this question randomly.
Do you think a relationship can still work if one person is religious and the other isn’t?
This is a potentially volatile question but it will give you a good insight into how keen he is to make a relationship work.
What’s your favourite part of a woman’s body?
It’s a fun, flirtatious question that’s good to ask any potential partner you might have.
What’s the most romantic thing you’ve ever done for a woman?
Find out how romantic he is! If he once surprised a woman with a cruise that very same day, you just know he’s probably gonna do something like this for you, too.
Would you describe yourself as a gentleman?
Or does he think chivalry is dead?
Do you think a relationship can work even if both people are looking for two different things?
Our thoughts are that it probably can’t – but you’re not asking us, are you?!
Does anything scare you?
Or is he a proper man who literally never gets scared by anything?
Is there anything you wouldn’t try?
Or is he one of those guys who is up for anything and everything?
Are you a monogamous person?
This is a key question because you need to know where a potential partner stands on this kind of thing?
If your new partner was in debt, would you shoulder it too and say “this is our debt now”?
Or is he gonna let you tackle it all by yourself?
When you need to calm down, what do you tend to do?
Find out how he reacts when things aren’t going his way.
Where do your talents lie?
What will his talents prove useful for if the two of you got into a relationship?
Do you speak any other languages?
Find out how smart he is!
What’s more important to you, security or freedom?
If I were to take away ALL of your possessions but left you with one, what would you want it to be?
The answer will be mighty revealing.
If you could pick between having money and having happiness, what would you take?
This is a pretty interesting question, but to impress you, he’s probably going to choose happiness. Ha.
Has life panned out how you thought it would?
Or did they think it would be better than this?
Or perhaps their life has turned out even better than they could ever have imagined?
Can you cook?
Or will they be expecting you to cook all the time omg?
Do you prefer to stay in swanky, posh hotels, or are you happy with a hostel?
Find out if they’ll be taking you to the very best places – or making you slum it!
Do you consider yourself to be a big drinker?
Let’s hope not!
Are sports a big part of your life?
And if they are, would they be willing to tone down their obsession now that you’re here?
What does music mean to you? Is it something casual or are you heavily into it?
Some people literally obsess over music. Others can take it or leave it.
What’s your favourite quote?
A persons favourite quote can give you a massive insight into how they look at life.
“Don’t be sad that it’s over – smiled that it happened.”
– Dr. Seuss
If you could be a certain age again, what age would you be? And why?
This will inspire a pretty cool answer as he reminisces about the best age of his life.
Just watch out for potential anecdotes about a “mental” lads holiday he once went on.
What does a lazy day mean to you?
Let’s hope he doesn’t have a lazy day every day?
If I wanted to spend an entire day under the duvet with you, would you be up for that?
Or would he get bored and start to feel lazy?
What do you think of negative people? Do you hang around them or do you cut them from your life?
How good is he at eliminating negativity from his life and focusing on the positives?
What’s the most irrational fear you have?
Let’s face it – it’s spiders, isn’t it?
What keeps you awake at night?
Every now and then, something comes along that keeps us awake at night. People get trigged by different things, from tax bills to cats that haven’t returned home yet. Find out what makes him anxious the most.
Are you a judgemental person?
We really hope he isn’t. That would suck!
If you were President for a day, what’s the first thing you’d do?
Let’s hope he doesn’t say anything totally insane here.
So here were the questions to help you get to know another person more deeply. We hope this was useful and you won’t have those awkward moments of silence on your dates any more.