Select Page

283 Deep & Fun Questions To Get To Know Someone [Big List]

283 Deep & Fun Questions To Get To Know Someone [Big List]

Are you looking for fun, deep, interesting personal questions to get to know someone better, for example during a date or with friends? Do you want to ask your friend original, exciting questions? In this article, you will find a nice question list with 223+ serious, profound and funny questions!

Below are the 283 most interesting questions you can ask. No mobile phone for a moment, but real attention to each other! With these questions, you can really get together and recall great memories, discuss the things that matter and dream together …

We start with the top 10 most interesting questions [Question set 1]

These questions give you an incredible amount of inspiration, positivity and opportunities for vulnerability. Impressive!

Question 1
What are you proud of? Name 10 things from the past year that you are proud of.

Question 2
What is something you wouldn’t say so quickly? Fill in: ‘ If you really knew me well, you would know about me that…’

Question 3
Fill in: ‘If I were really completely honest, I would say that …’ This is a question for ‘radical honesty’. What are the things you wouldn’t normally say? Things you would otherwise actually hide? For example, what are all your insecurities, fears and imperfections? What’s on your mind? What wants to be said? What do you need? What do you want? What do you feel like or don’t feel like?

Question 4
What kind of children did you play with when you grew up?

Question 5
What is the difference between your ideal self and your real self?

Question 6
What is the coolest topic you like to talk about? Or something you really want to tell people?

Question 7
What is going well (in your life)? What do you feel (most) grateful for in your life? What five things? Which persons? If you could thank one person – especially for this year – who would it be?

Question 8
Ask the wonder question . For example: ‘But so, suppose there was a wizard standing here and you could turn your life into anything you wanted, what would you do? What, who, where, why? ‘

Question 9
How do you envision your ideal life?  What kind of ideal planning of your working days and weekends are you working towards? What are your dreams? Go ‘ mastermind ‘ together and reflect , for example on all your life areas : career, health, family, relationships, relaxation, etc. This ensures the most distinctive, deep and beautiful conversations.

Question 10
What do you find most important in your life? In other words: what are your values? “What do you find important about …?” “Why are you doing what you are doing?” This question is part of the ‘logical levels’, a model with which you can send conversations into depth. Use the so-called ‘chunk technique’ to take questions step by step to go deeper through the logical levels:  ‘Also view the model with examples of the logical levels’ (click to get to the example questions) until you reach the highest level – mission – comes true.

“There are only four questions of value in life, Don Octavio. What is sacred? Of what is the spirit made? What is worth living for, and what is worth dying for? The answer to each is the same: only love.”
– Lord Byron

Use these fun questions about the personality of the other [Question set 2]

date questions

  • What is a crazy quality of yours? What is your most crazy property?
  • What do you normally never tell strangers about yourself?
  • How is your personality? Is it neat or untidy? Suppose you are packing your suitcase for a nice holiday. Do you roll, fold or throw everything in? Are you a folder or a prop?
  • Who is your favorite author / actor / musician / athlete?
  • Ask what the other likes about his / her hobby. Then try to trace that back to the personality or the emotions of the other.
  • Could You Live Without The Internet?
  • What is your ultimate vacation? Is it more active, relaxed, educational or social?
  • Have you ever broken anything? And what about rules?
  • Are you a cat person or a dog person? Or do you prefer to become a dragon trainer?
  • Are you happy with the person you are becoming?
  • What are you worried about and why?
  • Is the glass half full, or half empty?
  • Do you have bad habits?
  • Are you hiding something from someone?
  • Can you handle money well? In a responsible way?
  • Are you artistic and creative?
  • Have you ever cheated on a test?
  • Are you good at meeting new people and making new friends?
  • Before making a phone call, do you rehearse what you are going to say? Why?
  • What are the three things you can’t live without?
  • If you could change the way you were raised what would it be?
  • What are your secret talents?
  • What are your talents / specialties that make you unique?
  • What are your best and worst qualities?
  • If you could wake up tomorrow and suddenly gained an extra quality or skill, what would it be?
  • What gets you out of bed?
  • What is your favorite place and what can be found there?
  • Why is it a gift to have you as a friend?
  • What comment you have heard from someone else has stayed with you and will stay with you for a long time?
  • Ask the questions of the MBTI profiles. These tell a lot about a person’s personality.

Use these thoughtful questions to show deep interest [Question set 3]

deep questions are considerate

The questions below are so simple that they are often too easily forgotten. The simplicity of these questions is precisely its strength. Make it a habit to ask these questions of the people around you so that you are really considerate and show deep interest.

  • What are you thinking about now?
  • How are you doing now?
  • What is it? Really tell me what’s up, it relieves.
  • Where does the other want to go?
  • What does this person need now?
  • Does this person really feel heard?
  • How is your day?
  • What have you experienced?
  • Are you also working on a specific goal?
  • How are you feeling today?
  • How are you?

It is also very useful to show real interest in business contacts – for example with customers.

  • What do you think of what we do?
  • How is my service going for you?
  • What motivated you to start with x?
  • Who inspired you to start with x / do x?
  • Could you share your experience?
  • How did you become successful? How did you get to where you are now?
  • What benefits did you want to get from it?
  • What are you still missing?
  • What are some of your unforeseen needs?
  • What drives your satisfaction?
  • What is holding back your satisfaction?
  • What do you think is unique about us?

Ask about joys, fears and desires [Question set 4]

nice questions

  • What do you admire most about yourself?
  • What is your biggest insecurity?
  • When were you last rejected?
  • What are your imperfections?
  • What are you ashamed of?
  • What’s wrong? What are you currently facing?
  • What are your weaknesses?
  • Do you have bad habits?
  • What do you keep procrastinating that you actually know is important to change?
  • What are your good qualities and qualities ?
  • What is the quality that people compliment you on the most ?
  • What are 3 things about you that you wouldn’t want me to know?
  • Are you  also  afraid of spiders? What is your biggest fear, other than spiders?
  • What causes you (the most) stress? If a major concern could be taken away from you, what would it be?
  • What is your favorite part of the day?
  • What’s the most dangerous thing you’ve ever done?
  • Why do you think you are so beautiful?
  • What was the scariest moment in your life?
  • Have you had to go through difficult times in your life?
  • Have you ever had to endure (mental) illnesses?

Exciting, (not too) deep philosophical questions to ask [Question set 5]

  • What is the most beautiful and / or most important lesson you have learned in your life?
  • What are the questions that concern you most recently?
  • What thoughts have been on your mind lately?
  • What are the emotions you have been feeling the most lately?
  • What makes you think that the above thoughts, questions and emotions arise?
  • Do you think time goes faster as you get older?
  • How old do you feel right now?
  • What’s something about yourself that you absolutely love and what’s something you wish you were different? What part of yourself would you change if you could?
  • If you could change just one thing about your life, what would it be?
  • How much do you consider yourself worth?
  • If you could go somewhere where no one knew who you were, and where everything you did couldn’t be known to people you know, what would you like to do?
  • How do you view the world?
  • How can there be peace?
  • How do we get people closer together (creating community & peace)?
  • Finish the sentence: the world would be much cooler if …
  • Would you like me even if I didn’t have arms?
  • Go to the Askreddit webpage together  and answer the questions asked there.
  • If you could be an animal, which one would you be?
  • Is this the best time of your life?
  • If you could only own 10 things, what would they be?
  • What do you believe in? What are you convinced of? What are you absolutely sure about?
  • Do you believe people can create happiness or they just happen to get it?
  • What would you do if you could wear an invisibility blanket?
  • If you won a few million in the lottery tomorrow, how would you spend it?
  • Do you still believe in Sinterklaas?
  • Are there any aliens in parts of the universe?
  • What is love ?
  • Do you believe there is a soul mate for every person?
  • If you could have 3 wishes what would they be and why?
  • Do you see yourself as a happy person?
  • Are you satisfied with the life you have?
  • What everyday things make you happy?
  • What things can we do in the coming week to be happier?
  • What is a (most) important event in your life?
  • Have you ever wished you could have been born the opposite sex? Why?
  • If you could only do 1 thing for the rest of your life, what would it be?
  • What are the three things you can’t live without?
  • If you knew you would suddenly die in a year, would you make a change in the way you live now? Why?
  • What role does love play in your life?

Read this next:  This is how you deal with know-it-alls [5 Techniques]

Do you really want to know someone better? Ask about passions, ambitions and life mission [Question set 6]

  • What is your passion, what makes you excited?
  • Teach me something interesting about what you are passionate about!
  • What’s the reason you get up?
  • Why do you get up every day?
  • Why am I doing what I do?
  • What do you really want? If you weren’t scared?
  • Do you know what you want to get out of your life? (No? What are we doing here, are we in 8th grade here? Is your mother coming down with cookies and milk?)
  • Do you currently have goals that concern you? What is your dream?
  • What are the 3 most important things in your life?
  • Which place in the world would you visit anyway?
  • What does your bucket list look like?
  • What would your dream house look like?
  • What can or am I contributing to the greater whole? In other words: what is my mission? How big is my effect at the moment and how big can my effect be?
  • What would you like to achieve in your life?
  • What is the greatest achievement in your life?
  • What makes you happy in life? What makes you happy?
  • What are you obsessive about?
  • What do you really want? What does your best life look like?
  • When you daydream, what do you see yourself doing?
  • And what is stopping you? Also use the other questions of the outcome model.
  • Have a kind of ‘mini Mastermind session’ together. Click here for all related questions.
  • How do you envision an ideal family life? How are the roles and tasks divided?
  • Would you ever want children? How much? Why? When? How would you raise them? With what values?
  • What role would spiritual activities play in your family life? Would you open up your home to invite others to spiritual activities?
  • What level of prosperity do you strive for? What level would be acceptable to you? What standard of living are you used to?
  • What would you do if you didn’t have to think about time or money?
  • What would you do if you weren’t afraid?
  • What is the decision you are avoiding or delaying?
  • What are you now tolerating that actually needs to change so that you can move forward?
  • What do you secretly know that you should say ‘no’ to it?
  • What do you secretly know that you have to stop saying ‘yes’ to it?
  • What in your life is draining your energy and motivation right now?
  • What are three things you do regularly that don’t serve or support you?
  • In what way is the current situation completely perfect?

Ask for the advice and opinion of the other person [Question set 7]

interesting questions

  • “What is your rule of thumb for success?
  • “How do you feel about getting married? And cheating?”
  • Ask his / her opinion about something that is currently on your mind. It could be anything: “What is your opinion about fear of contamination?”
  • “How would you handle x?” For example, “What would you say to someone trying to commit suicide?”
  • “What do you do when you have a difficult day?”
  • “Can you name three of my strengths?” This also uses the power of compliments.
  • “What kind of vibes are you picking up from me?” “In other words: what feelings do you get from the energy that I radiate?”

Exciting questions about people, emotions, relationships and drama [Question set 8]

  • You can invite 5 people to dinner. Real or fictional people, from any place or time. Who do you invite and why? (This tells you a lot about what kind of people the other person thinks is important to have around them.)
  • What’s the meanest thing you’ve ever called a man?
  • When was the most difficult moment when you tried not to laugh?
  • Simpler version: When was the last time you laughed really hard? Bonus Tip: Anchor this happy feeling with yourself!
  • What’s the most embarrassing thing you’ve ever done?
  • What’s the most embarrassing thing you’ve ever seen?
  • What’s the worst restaurant experience you’ve had?
  • What can really move you?
  • What music hit you hard?
  • What made you cry?
  • When did you feel a tingling of happiness rushing through your body?
  • When did you enjoy peace and quiet?
  • What does your name mean?
  • What do your friends think of me?
  • Can you know someone is lying to you?
  • Have you ever gotten ultimate revenge on someone?
  • Are you good at putting a smile on other people’s faces?
  • Have you ever stood up for someone you barely knew?
  • How do you deal with disagreements and conflicts?
  • How do you express your emotions?
  • When was the last time you cried?
  • Do you easily get stressed? And what makes you stressed?
  • What irritates you easily? Who irritates you easily?
  • What kind of people are you allergic to? And with what kind of people?
  • Where do you add stress to your life?
  • How would you look at this in a month, a year, or ten years from now?

Original questions about the youth years of the other [Question set 9]

  • How were you as a child?
  • How would you describe yourself when you were 5-12 years old?
  • Who was your greatest idol as a child?
  • What did you want to become as a child?
  • What did you learn about men / women growing up?
  • What are 3 or 4 of your first childhood memories?
  • What is your most cherished memory?
  • Where did you grow up / Where are you from? What was it like growing up there, what was your favorite area there? What are your best memories of that?
  • Have you ever had an imaginary friend as a child?

Ask about family and friends [Question set 10]

funny questions date

  • Do you have brothers and sisters? How much?
  • What are their names?
  • How old are they?
  • Wat are they doing?
  • Do you look alike?
  • Do you have a similar character?
  • Do you describe relationship with your parents?
  • What does a good friend mean to you?
  • Describe your best friend.
  • Are you a good friend?
  • Do you miss someone very much right now? Who is that?
  • What do you like to do with friends in your spare time?
  • Give me the names of 3 people you like most in your life and why?
  • What do you value most in friendship?
  • Who in your family was so good at inspiring you to be so kind and open?
  • How warm and close is your family? Was your childhood happier than most other people’s childhoods?
  • What’s your partner’s best and worst quality? This question is extra fun if his / her partner is also there.

You can also ask original questions about work or study [Question set 11]

  • Where do you work? Do you have cool colleagues?
  • What would your dream job be if money wasn’t an issue?
  • What do you want to be when you’ve grown up? Don’t say princess!
  • Why this study and not something else?
  • What has really been on your mind lately?

Fun questions about hobbies [Question set 12]

  • What is your favorite thing or activity in the world?
  • What is your favorite movie and why?
  • Is there a book or movie that has made a huge impact on you?
  • Are you reading? Which books would you take to a deserted island?
  • What is your typical Saturday night like?
  • Cool people are a dying breed. What do you do for fun?
  • What do you like to do? These things feed your spirit, or your intuition. In this article you will find more such questions.

Other funny questions with positive emotions [Question set 13]

get to know someone better

  • If you could only have 1 dish for the rest of your life, what would it be?
  • What is your favorite candy?
  • Have you ever stolen something from a store or someone?
  • What are your favorite and least favorite foods?
  • If you were to write an entry in your diary about our meeting, what would you write?
  • Do you do crazy dances when no one is watching?
  • Describe your perfect day!
  • How did you become the person you are today?
  • Are you good at computer games?
  • Can you share 3 good points about me?
  • Can you fake accents?
  • How do I smell?
  • Do you still smile with your teeth when a picture of you is taken?
  • Do you have a recurring dream? What happens in it?
  • Did someone help you figure out how you were going to ask me on a first date?
  • Do many people underestimate or overestimate you?
  • Have you ever been addicted to a game? Which?
  • Do you enjoy being in nature?
  • Do you scream in rollercoasters?
  • Can you imitate others well?
  • Do you keep a diary or something?
  • Tell me something interesting about yourself.
  • When was the last time you broke the rules / did you do something impulsive?
  • What are 3 reasons why you want to get to know me? What are 3 reasons why I would like to get to know you?

Ask these original questions about falling in love [Question set 14]

funny original questions

Time for the best sweet and sexy questions. Be extra vigilant with these questions. It is generally inadvisable to go ‘meta’ about falling in love. ‘Meta’ means that you are going to talk ‘about’ something that you are actually  doing  . If you  talk about  falling in love while you are experiencing falling in love with someone, it can greatly diminish the mysterious feeling of falling in love because you are no longer in the middle of it but start looking at it from a distance.

So feel well in which way you ask these questions so that you do not get too out of the emotion of your own meeting. Little hint: These questions are great for when you’ve known each other for a while and it’s time to build comfort by getting to know each other better. There are also some pretty tough questions.

  • What traits do you find attractive in boys / girls?
  • What does your ideal partner look like?  What wishes should he / she meet?” If you meet it yourself, there is a match!
  • When was the last time you went on a date ?
  • When was the last time you fell in love?
  • What was the longest time it took a boy to kiss you and what was the shortest time?
  • What kind of clothes do you find sexy about a man? Just say the masculine equivalent of a visible thong in women.
  • What’s the most absurd thing you’ve ever done to impress a crush?
  • What are your turn-offs and turn-ons?
  • How was your first kiss?
  • Who should make the first move : the man or the woman?
  • What do you think are the most important qualities in a man?
  • What can get you totally impressed?
  • Are you too shy to ask someone out?
  • Are you obsessed with me?
  • Are you a kissable person?
  • Have you ever cheated on you?
  • Do you ever set your friends up for blind dates?
  • Are you stalking me?
  • Have you ever been rejected by a crush?
  • What’s the funniest pick up trick done on you?
  • Do you believe in love at first sight?
  • What is your interpretation of a romantic evening?
  • How do you express your love and affection ?
  • What have you learned from previous relationships? How would you approach things differently now?
  • What’s your best sexual experience ?
  • When was the last time you had really really good sex?
  • What do you like in bed?
  • Are you sweet / soft or dark in bed?
  • When did you go all out and lose all inhibitions?
  • What was the most exciting place you had sex? Where would you ever want to do it?
  • If you weren’t judged, what freaky weird sex idea do you have that wouldn’t tell you?
  • What’s the sexiest thing you’ve done for a boyfriend / girlfriend?
  • Suppose your dream man / dream woman comes in here. How would you seduce him / her?

Crazy questions: Dilemma on Tuesday [Question set 15]

Use the following dilemmas from the Dutch book: Dilemma on Tuesday . There are also a lot of ‘awkward questions’ (embarrassing questions). By the way, this book with ‘this or that questions’ is highly recommended!

  • Would you rather live in a world where giant friendly gummy bears roam or in a world where hoverboards are widely available in stores?
  • Do you prefer legs as long as your fingers or fingers as long as your legs?
  • If you had to choose between being drawn to watermelons and having an orgasm every time you hear the word pancake, which one would you choose?
  • Would you rather give up on the internet or your friends and family?
  • Would you rather change sex every time you sneeze, or not be able to tell the difference between a muffin and a baby?
  • For women: would you rather have breasts on your back or no breasts at all?
  • Would you rather discover the cure for cancer or end earth hunger?
  • Would you rather be happy in an unhappy world or unhappy in a happy world?
  • Would you rather have the ability to lift 45 kg telekinetically, or 4,500 kg physically?
  • Would you rather have the ability to speak any language fluently, or masterfully play any instrument?
  • Would you rather sing the song “Sexy Back” every time you talk to someone of the opposite sex, or sing the song “Africa” ​​every time you talk to a black person?
  • Would you rather have someone poke you constantly for the rest of your life or you never get touched by anyone again?
  • Would you rather be the smartest or the most stupid person on the planet? In both scenarios, you maintain the same level of intelligence that you have now.
  • Would you rather have a magic hat that you can put on everyone with the words ‘my lord / my wife’, or would you rather have the ability to run 5x faster when you stretch your arms behind your back and make airplane noises?
  • Would you rather be able to rewind 60 minutes every day, or freeze for 60 minutes every day?
  • Would you rather receive 100,000 and have your beauty doubled, or receive 10 million and have your beauty cut in half?
  • Would you rather win 500,000 or would you rather win a billion but then you will never be able to use the internet again?
  • Everything you say is dubbed in German – or – you are always chased on the street by a barrel organ.
  • Your body skin is croquette crust – or – there’s always a dwarf walking next to you saying you’re lying.
  • No one ever laughs at what you say – or – you always laugh when someone cries.
  • Everyone hears what you think – or – you hear what everyone thinks
  • You can play all instruments – or – you can speak all languages.
  • Would you rather have the ability to know if someone is lying to you (this only works if that person is talking to you directly and you don’t know the exact truth – just that that person is lying) or do you want to have the ability to tell everyone’s sexual preferences and know deepest, darkest sexual fantasies (as long as this person is in your field of vision)?
  • There are cameras all over the house and the livestream is on – or – you develop an allergy to your friends and family.
  • You live on the 94th floor flat with no lift – of – all your digital communication needs via handwritten letter.
  • Either find the love of your life and have no friends – or have lots of friends but never fall in love.

Game mode: The Truth Game (Truth questions: great for a date!)

original questions date

This game ensures that you have a common thread to talk about things so that, when it comes to a halt, you can go to the next question:

‘I’m going to ask you 3 questions and you are going to ask me 3 questions. All 3 questions must be answered. By the way, you cannot copy a question.

Here are some sample questions to get you started:

  • Tell me a secret.
  • If you could change 1 thing about yourself, what would it be?
  • When was the last time you felt jealous?
  • How many boyfriends have you had?
  • Would you like to kiss me?

Afraid of ‘interview mode’? Tips to avoid this while asking date questions …

You know it: one question after another, and that gives you a hard character, without you having intended it that way. Fortunately, there are three solutions to this:

  • This is the most elegant trick: alternate questions with statements, or even better: ask your question in statement form. You can find examples and additional explanation of this technique in the article with flirting tips.
  • Use the technique: language softeners. This is an excellent remedy for interview mode. You can find all about it in the accompanying article on language softeners .
  • Before asking the question, you can ask an introductory question: Can I ask you something crazy?

The secret to these fun questions: don’t memorize them for your date!

The questions in this article are ideal for dates – especially dates arranged through a good dating site . However, there is a small downside to asking questions.

You might recognize it: I’ve been on first dates where the woman started asking such a typical ‘date question’ out of nowhere. I thought it was funny, but it really took her out of her natural flow, and with that the entire date. So that’s the disadvantage of these kinds of questions.

Still, I encourage you to read this article with interesting questions. These types of questions build towards a deep connection, so it is certainly worth knowing a little how to send your date or relationship in depth .

Read through all these questions and then let them go! They will naturally come to mind when the situation calls for it. During a date, the intention is to have a good vibing without having to think about all kinds of things. If you want to remember a number of them, stick to a maximum of 1 or 2 questions.

The best questions for getting to know someone… aren’t questions at all

Do you want to get to know someone? Most information about the other person is obtained through …

  • Looking the other in the eye.
  • A hug.
  • Shaking the hand.

How someone does the above things reveals the most about the other.

This was the interesting questionnaire! My other articles are just as long and useful!

This was an extensive article, didn’t you think? My other articles are just as extensive and valuable!

So take a look at… my other super comprehensive and helpful articles on dating and relationships . You will find the best tips and advice to learn more about this topic, such as this article with 70+ flirting tips.

Have fun together with all these deep questions!

These were all the fun, interesting questions you can use to get to know someone. For example during a date! Use these original questions for your boyfriend or girlfriend. Have fun with this questionnaire full of serious and funny questions. Do you know more fun questions to ask? Add your suggestions in the comments!

About The Author


Hello! Thanks for reading these articles. My intention is to make happiness as simple and clear as posssible. By the way, excuse my English. I am not a native English speaker since I live in Amsterdam. Much appreciated if you use the comments to make suggestions on my grammar. See ya in another blogpost!