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

223 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 223 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 of the past year that you are proud of.

Question 2
What is something that you would not tell so quickly? Fill in the blanks: ” If you really knew me well, you would know about me that…”

Question 3
Fill in the blanks: “If I really were completely honest, I would say that …”

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 going well (in your life)? What do you feel (most) grateful for in your life?

Question 7
How do you see your ideal life? What is the ideal setup for your workdays and weekends?

Question 8
Ask the ‘what if question’. For example: ‘But suppose there was a wizard here and he could turn you into anything you want, what would you do? What, who, where, why?’

Question 9
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…?”

“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 person [Question set 2]

date questions
  • What is a crazy feature of you? What is your most crazy characteristic?
  • What do you normally never tell strangers about yourself?
  • What is your personality like? Is it neat or untidy? Suppose you pack your suitcase for a great holiday. Do you roll, fold or throw everything in?
  • Who is your favourite author / actor / musician / athlete?
  • Ask what the other person likes about his / her hobby. Then try to connect that back to the personality or emotions of the other person.
  • Could you live without the internet?
  • What is your ultimate vacation?
  • 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?
  • Are you artistic and creative?
  • Have you ever cheated on a test?
  • Are you good at meeting new people and making new friends?
  • Before you make 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?
  • If you could wake up tomorrow and you suddenly had an extra attribute or skill, what would that be?
  • What is your favourite place and what can you find there?
  • Why is it a gift to have you as a friend?
  • Which remark that you have heard from someone else has always stayed with you and will you remember for a long time?

Ask for joys, fears and desires [Question set 3]

deep questions
  • What do you most admire about yourself?
  • What is your biggest uncertainty?
  • What are you ashamed of?
  • What’s bothering you? What are you currently struggling with?
  • What do you always postpone, which you actually know is important to change?
  • What are your good qualities and traits?
  • What is your one characteristic about which people give you the most compliments?
  • 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, except for spiders?
  • What gives you (the most) stress? If a major concern could be taken away from you, what would it be?
  • What is your most favourite part of the day?
  • What is the most dangerous thing you have ever done?
  • Why do you think you are so beautiful?
  • What was the scariest moment in your life?

Exciting, (not too) deep philosophical questions to ask [Question set 4]

  • What is the most beautiful and / or most important lesson you have learned in your life?
  • Do you think that time goes faster as you get older?
  • What is something about yourself that you absolutely love and what is something that you wished to be different? Which part of yourself would you change if you could?
  • If you could go somewhere where you are absolutely anonymous and where everything you did could not become known to people you know, what would you want to do?
  • How do you view the world?
  • How can peace be established?
  • How do we get people closer to each other (creating community & peace)?
  • Complete the following sentence: the world would be much cooler if …
  • Would you also like me if I didn’t have arms?
  • Go to the Askreddit webpage together and answer the questions asked there.
  • If you could be an animal, what would you be?
  • Is this the best time of your life?
  • If you could only own 10 things, what would they be?
  • Do you believe that people can create happiness or that they just stumble upon 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 Santa Claus?
  • Are there aliens in parts of the universe?
  • What is love?
  • Do you believe there is a soulmate for every person?
  • If you could make 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 were born as the opposite sex? Why?
  • If you could only do one thing for the rest of your life, what would it be?
  • What are the three things you can’t live without?
  • If you knew that in a year’s time you would suddenly die, would you make a change in the way you live now? Why?
  • What role does love play in your life?

Ask these original questions about falling in love [Question set 5]

funny original questions

Time for the best sweet and sexy questions. Be extra careful about these questions. After all, it is generally not advisable 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 being in love because you are no longer in the middle of it but looking at it from a distance.

So use your feeling about how you ask these questions so that you don’t lose too much of the actual emotions of falling in love. Small hint: these questions are suitable for when you have known each other for a while and it is time to build up comfort by getting to know each other better.

  • What qualities do you find attractive in boys / girls?
  • When was the last time you had a date?
  • When was the last time you fell in love?
  • What was the longest time it took someone to kiss you and what was the shortest time?
  • What is the most absurd thing you have 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 are the most important qualities in a man in your experience?
  • 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 someone?
  • Do you ever set up your friends for blind dates?
  • Are you stalking me?
  • Have you ever been rejected by a crush?
  • What is the funniest pickup line that has been applied to you?
  • Do you believe in love at first sight?
  • What is your interpretation of a romantic evening?

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

  • Teach me something interesting about what interests you!
  • Do you know what you want to get out of your life? (No? What are we doing here, are we in group 8 here? Is your mother coming down with cookies and milk?)
  • Do you currently have goals that are keeping you busy? What is your dream?
  • What are the 3 most important things in your life?
  • Which place in the world would you per se visit, no matter what?
  • 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?
  • Why do you do what you do?
  • What would you like to achieve in your life?
  • What is the greatest thing you have achieved in your life?
  • What makes you happy in life?
  • What are you obsessive about?

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

interesting questions
  • “What is your rule of thumb for success? “
  • “How would you tackle x?” For example: “What would you say to someone trying to commit suicide?”
  • “What do you do if you have a difficult day?”
  • “Name three strong points of mine?” This question also uses the power of compliments.

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 finds important to have in his / her environment.)
  • What is the meanest thing you’ve said to someone (who fancied you)?
  • When was the hardest moment when you tried not to smile?
  • Simpler version: When did you last laugh very hard?
  • What is the most embarrassing thing you’ve ever done?
  • What is the most embarrassing thing you’ve ever seen?
  • What is the worst experience in a restaurant that you have had?
  • What can really make you emotional?
  • What does your name mean?
  • What do your friends think of me?
  • Can you tell that someone is lying to you?
  • Have you ever taken the ultimate revenge on anyone?
  • Are you good at putting a smile on the faces of other people?
  • Have you ever stood up for someone you barely knew?

Original questions about the childhood of the other person [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 be as a child later?
  • What did you learn about men / women when you grew up?
  • What are 3 or 4 of your first childhood memories?
  • What is your most cherished memory?
  • Where did you grow up / Where do you come from? What was it like to grow up there, what was your favourite area there? What are your best memories of that?
  • Have you ever had an imaginary friend as a child?

Ask for 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?
  • What are they doing?
  • Are you alike?
  • Do you have a similar personality?
  • Describe your relationship with your parents?
  • What does a good friend mean to you?
  • Describe your best friend.
  • Are you a good friend?
  • Are you really missing someone right now? Who is that?
  • What do you like to do with friends in your free time?
  • Give me the names of 3 people you like the 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 the youth of most other people?

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 princes!
  • Why this study and not something else?
  • What has been keeping you busy lately?

Great questions about hobbies [Question set 12]

  • What is your favourite movie and why?
  • Is there a book or movie that has made a huge impact on you?
  • Are you reading? Which books would you bring to a deserted island?
  • What does your typical Saturday evening look like?
  • Cool people are a dying breed. What do you do for pleasure?
  • What do you like to do? Things that feed your spirit or in other words: your intuition.

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 that be?
  • What is your favourite candy?
  • Have you ever stolen anything from a store or from someone?
  • What are your favourite and least favourite dishes?
  • If you would write a piece in your diary about our meeting, what would you write?
  • Do you do crazy dances when nobody 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?
  • Are you still laughing with your teeth when you take a picture?
  • Do you have a recurring dream? What happens there?
  • Has anyone helped 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 one?
  • Do you enjoy being in nature?
  • Do you scream in rollercoasters?
  • Can you properly imitate others?
  • Do you keep a diary or something?
  • Tell me something interesting about yourself.
  • When did you last break 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?

Crazy questions: Dilemma’s… [Question set 14]

Use the following dilemmas from the Dutch book: Dilemma on Tuesday. There are also many ‘awkward questions’ (embarrassing questions). This book with ‘this or that questions’ is highly recommended, if only it also existed in English… But luckily I translated some of them here:

  • Would you rather live in a world where giant, friendly gummy bears roam freely or in a world where hoverboards are available everywhere 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 attracted to watermelons, and getting an orgasm every time you hear the word pancake, what would you choose?
  • Would you rather give up the internet or your friends and family?
  • Would you rather change your sex every time you sneeze or not see 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 medicine for cancer or end the hunger on earth?
  • Would you rather be happy in an unhappy world or unhappy in a happy world?
  • Would you rather have the skill to lift 45 kg telekinetically, or 4,500 kilos physically?
  • Would you rather have the ability to speak every language fluently, or to master each instrument?
  • Would you prefer to sing the song ‘Sexy Back’ any time you talk to someone of the opposite sex, or sing the song ‘Africa’ any time you talk to a black person?
  • Would you prefer that someone would constantly poke you for the rest of your life or that you will never be touched by anyone again?
  • Would you rather be the smartest or the most stupid person on earth? In both scenarios, you maintain the same level of intelligence that you have now.
  • Would you rather have the opportunity to rewind 60 minutes every day, or to freeze time for 60 minutes every day?
  • Would you rather receive 100,000 and get your beauty doubled, or receive 1 million and get your beauty cut in half?
  • Would you rather win 500,000 or would you rather win a billion but then you can never use the internet again?
  • Your body skin is made of croquette crust – or – there is always a dwarf next to you who says that you are lying.
  • No one ever laughs at what you say – or – you always have to 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) or do you want to have the ability to know everyone’s sexual preferences and know the deepest, darkest sexual fantasies (as long as this person is in your field of vision)?
  • There are cameras everywhere in the house and the live stream is on for the whole world to see – or – you develop an allergy for your friends and family.
  • You live on the 94th floor flat with no elevator – or – all your digital communication needs to go via handwritten letters.
  • Find the love of your life and have no friends – or have many friends but never fall in love.

Questions Game: The Truth Game (Truth Questions: Excellent for a Date!)

original questions date

This game ensures that you have a common thread to talk about so that when an awkward silence is threatening to appear, you can go to the following question:

‘I’m going to ask you 3 questions and you will 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 changed 1 thing about yourself, what would it be?
  • What’s the last time you felt jealous?
  • How many friends have you had?
  • Would you like to kiss me?

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

I’m sure you recognize this: one question after the other, and that gives you both an unpleasant feeling. Fortunately, there are three solutions for this:

  • This is the most elegant trick: alternate questions with statements, or even better: ‘ask’ your question in statement form. In stead of: ‘What kind of work do you do?’ you say: ‘I bet you’re a teacher.’
  • Use the technique of ‘language softeners’. This is an excellent remedy for interview mode. You don’t say: ‘What kind of work do you do?’ but you add a softener: ‘I wonder what kind of work you do…’
  • Before you ask the question, you can ask an introductory question: ‘Can I ask you something crazy?’

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

Perhaps you recognize it: I have been on first dates where – from scratch – the woman started asking such a typical ‘date question’. I thought it was funny, but it really brought me and her out of our natural flow, and with it the whole date. That is the disadvantage of these types of questions.

Still, I encourage you to (re)read this article with interesting questions. This is because these types of questions build towards a deep connection, so it is certainly worth knowing a little about how you can send your conversation, date or relationship into depth.

Read all these questions and then let hem go! They will naturally occur to you if the situation demands it. During a date, the intention is to have a nice vibe without having to think about all kinds of things. If you want to remember a number of questions per se, keep it to a maximum of 1 or 2 questions.

This was the interesting and deep questions list!

This was an extensive article, didn’t you think? These were all fun, interesting questions that you can use to get to know someone. For example during a date!

Use these original questions, for instance, with your boyfriend or girlfriend. Have fun with this question list full of serious and funny questions. Do you know any more fun and deep questions to ask? Add your additions to the comments!

About The Author


Hello! Thanks for reading my articles. Happiness is my big subject. 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!

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Who is Happy Rubin?

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Dear reader, thank you so much for dropping by on this curious happiness blog. I want to inspire you to get the best out of your life. Being happy and following your heart are my subjects.

Have fun with reading!