25 Questions to Start Interesting, Deep Conversations

Questions about the past

The past creates us in the present, which is why it is so important. Yes, people change, but not as quickly as we would like. Therefore, the one who betrayed once will repeat it again. Questions about the past will help you understand your friend and trace the connection between his present and past.

Childhood

Have you ever kept a diary?
Did you like going to kindergarten? What did you dislike the most?
Was it easy to study at school?
What changed you as a teenager?
Who was your first love?
Do you communicate with your classmates and school friends?
Do you have Brother or sister? Are you a good communicator?
If you were asked to change something about your childhood, what would you choose?
What did you dream of becoming as a child?
What were your hobbies, what sections and clubs did you attend?

Biography

What was the best period in your life?
What was the worst period in your life?
Have you ever lost someone close to you?
When did you feel the biggest adrenaline rush?
Which of your parents are you closer to and why?
What are you most grateful for?
What did your last relationship teach you?
What is your biggest regret in life?

drunk guest

Have you started a new job and need to establish relationships with your team, but don’t know where to start the conversation? We offer a list of 100 questions that will help you get to know a person better.

Who is your hero?
If you could live anywhere, where would it be?
What are you most afraid of?
What's your favorite family vacation?
What would you like to change about yourself if you could?
What really makes you angry?
What motivates you to work hard?
What do you enjoy most about your job?
What are you most unhappy about in your job?
What is your greatest achievement?
What is your child's greatest achievement?
What is your favorite book?
What makes you laugh the most?
What was the last movie you went to? What do you think of him?
What did you want to be when you were little?
What does your child want to be when he grows up?
If you could choose to do anything during the day, what would it be?
What is your favorite game or sport?
Would you rather: ride a bike, ride a horse, drive a car?
What song would you sing karaoke all night?
What two radio stations do you listen to most often in the car?
What would you rather do: wash the dishes, mow the lawn, clean the bathroom, or vacuum the house?
If you could hire an assistant, what would you do? For help with cleaning, cooking, or working in the garden?
If you could only eat one dish for the rest of your life, what would it be?
Who is your favorite author?
Have you ever had nicknames? Which?
Do you like or don't like surprises? Why or why not?
In the evening, would you rather play, visit relatives, watch a movie or read?
Would you rather vacation in Hawaii or Alaska, and why?
What would you like more: winning the lottery or having the perfect job? And why?
Who would you send to a desert island?
If there was no money, what would you do all day?
If you could go back in time, what year would you go to?
How would your friends describe you?
What are your hobbies?
What's the best gift you've ever received?
What's the worst gift you've ever received?
Aside from the essentials, what's the one thing you still can't live without all day?
List two problems with keeping pets.
Where do you see yourself in five years?
How many pairs of shoes do you have?
If you were a super hero, what super powers would you have?
What would you do if you won the lottery?
What type of public transport do you prefer? (plane, train, bus, car, etc.)
What is your favorite pet?
If you could go back in time to change one thing, what would it be?
If you could have lunch with any 4 people, who would they be?
How many pillows do you sleep on?
How long have you been awake at most (and why)?
What's the tallest building you've climbed?
Would you choose intelligence or looks?
How often do you buy clothes?
Have you ever had a secret admirer?
What is your favorite holiday?
What's the bravest thing you've ever done?
What's the last thing you recorded on TV?
What was the last book you read?
What's your favorite foreign food?
Are you a clean or dirty person?
If they made a film about your life, who would play you? Which actor?
How long does it take you to get ready in the morning?
What kitchen appliance do you use every day?
What's your favorite fast food?
What's your favorite family recipe?
Do you love or hate roller coasters?
What's your favorite family tradition?
What is your favorite childhood memory?
What is your favorite film?
How old were you when you found out Santa didn't exist? How do you know?
Is your glass half full or half empty?
What's the craziest thing you've done in the name of love?
What three items would you take with you to a desert island?
What was your favorite subject at school?
What's the most unusual dish you've eaten?
Do you collect anything?
Is there anything you would like to bring back into fashion?
Are you an introvert or an extrovert?
Which five senses do you consider the most powerful?
Have you ever had a surprise party? (that was a real surprise)
Do you have any famous relatives?
What do you do to keep fit?
Does your family have a motto?
If you were the ruler of your country, what would be the first law you would introduce?
Who was your favorite teacher at school and why?
What three things do you think are most important to do every day?
If you heard a warning, what would you respond?
Do you have a song that seems to be sung about you?
Which celebrity would you have a cup of coffee with?
Who was your first love?
What's the most interesting thing you can see from your office or kitchen window?
On a scale of 1-10, how funny are your jokes?
Where do you see yourself in 10 years?
What was your first job?
If you could join any music group, past or present, which one would you want to join?
How many languages do you know?
What is your favorite family holiday, traditions?
Who is the smartest person you know?
What animal do you identify with?
What thing would you never do again?
Who knows you best?

Translation: drunk guest

Questions about love, family and friendship

It is a similar view of family values and friendship that determines the longevity of a relationship. These questions will open your eyes to many nuances that you didn’t even know about.

Man and woman

What is a stumbling block for you in a relationship?
Could you take back someone who committed treason?
Would you share your password with your partner?
When do you think a person is ready to get married?
How will you react if your parents don't like your chosen one?
Do you usually stay friends with your exes?
When was the last time you broke someone's heart?
Could you move for love?
What do you think about online dating and Tinder?
Do you think quarrels are sometimes necessary or should there always be an idyll?

Love and money

Can you fall in love with a very fat person if he is rich?
How do you feel about relationships for money?
Are you ready to support your soulmate?
Should both people in a couple earn the same amount or is it not important?
Should the budget be shared or does everyone pay only their own expenses?
What is better: “heaven in a hut” or a marriage of convenience?
A comfortable life or true love – what will you choose?
Is it possible to start a family if both are unsteady on their feet?
Will you be comfortable if the chosen one is much richer than you?

Love and children

What kind of parent do you think you will be?
How do you feel about abortion?
How much does it cost to have a child?
How many children do you want?
Can you raise someone else's child?
Will you live with an unloved person just because of the child?

Love and sex

How do you feel about explicit messages with photos?
What is acceptable for you in intimacy?
Are you ready to support what your chosen one offers, if you haven’t tried it before?
Have you ever been in a loveless relationship?
Do you believe in love or do you think it's just attraction?

Your relationship

Who is the person you can talk to about literally anything?
Could you tell me if you killed a person?
Who would you invite with you if you decided to do something illegal?
What sometimes irritates you about me?
What's your favorite way to spend time with me?
Is it easy for you to communicate with me, do you get emotional relief?
What do you think we have in common?
Do you like my friends?
Do you want us to be friends for life?

Questions about remote work

How do you prefer to work: at home or in the office? Why? Would you like to combine remote work and office work and, if so, how?
What is the most challenging thing about working remotely for you? And the simplest thing?
Do you have your own “office” (separate workplace) at home?
Will you show us your “remote” workplace?
Where do you most often work from home? At your desk? At the kitchen table? On the balcony? On the couch? In your favorite chair?
Let's be honest, how often do you work while lying in bed?
What does your morning routine look like when you work from home and don't have to get ready to go to the office?
What is your top life hack to avoid distractions while working from home?
How do you stay productive and motivated while working remotely?
What does your remote work outfit look like? Do you wear Hawaiian shorts under a dress shirt because you still can't see the bottom on a video call?
How many cups of coffee/tea do you drink per day?
Are you a morning person or a night owl? When is it most convenient to work and is it possible to organize a convenient schedule remotely?
How do you think we can improve our calls?
Do you like to drink caffeinated drinks (tea, coffee, cola) while working?
What good movie or TV series have you watched lately?
Which book do you think is the best you have read and why?
What do you consider the best professional literature?
If you could learn one new hard skill soon, what would it be?
If you could develop one new soft skill any time soon, what would it be?
Do you like to play sports? What sport do you like best?
If you could write a book, what genre would you choose? Fantasy? Thriller? Novel? Historical fiction? Professional literature?

Typical questions

These are common questions you might ask during your first meeting. There is nothing deep or aggressive about them, they are simple, quite cheerful and curious.

Where did you/are you studying?
Do you like to travel?
What was your favorite subject at school?
...What's your least favorite subject?
Do you play any musical instruments?
What genre of films do you like?
Do you like sweets?
Are you into sports?
What did you spend your first salary on?
Do you like extreme sports?
What is your favorite season?
What's the craziest thing you've done while drunk?
What is your favorite foreign country?
Do you like your job?
Have you ever had a really bad partner/boss?
Do you like watching horror films?
Do you know any foreign languages?
Tell me about your family. Who are they? Are there any brothers/sisters?
What do you like best? City or village?
Have you ever thought about moving to another city or country?
Whom you studied?
When was the last time you were on vacation?
Can you tell me about the worst teacher you ever had?
When was your first kiss?
What's your favorite cuisine?

Questions with a touch of philosophy

What's the best advice you've ever received?
What do you think are the most amazing scientific discoveries?
What are you dreaming about?
If you were to compete in a Miss/Mr World type competition, what would you enter in the talent competition?
What would you title your autobiography?
Imagine being very rich and no longer having to work. What would you do?
If you had to delete all but 3 apps from your smartphone, which ones would you keep and why?
What is your favorite magical or mythological animal?
Who is your favorite fairy tale character? Would you like to be in his/her place?
Tell us about your dream house/apartment.
Imagine that you are about to sail around the world. What would you name your ship and why?

Funny Questions

The zombie apocalypse is coming, assemble a team of three people. Why did you choose these people?
Which emoji/sticker do you use most often?
Tell us about your worst/inappropriate outfit?
What about the worst haircut?
Who was your favorite actor/actress growing up?
Are you compared to any celebrities? With whom?
If you could bring back any fashion trend, what would it be?
What type of transport do you like most?
Imagine hosting your own late-night talk show. Who would you invite as your first guest?
Imagine that a film is being made based on your biography. What genre would it be and who would play you?
Do you want to become famous? In what area?
Do you like to sing karaoke? What's your favorite song?
What food did you hate as a child? How do you feel about this now?
If you had to eat one thing for the rest of your life, what would it be?
Imagine that you have a choice: to remain on a desert island alone or with your worst enemy. Which would you choose and why?
If aliens flew to Earth tomorrow and asked you to fly with them, would you agree?
60s, 70s, 80s, 90s: which decade do you love most and why?
What's your favorite thing you bought this year?

“If only” questions

If you could talk to any fairy tale/movie character, who would you choose and why?
If you could live in any country for a year, which would you choose and why?
If you could commit any crime and get away with it, what would you do and why?
If you could see any movie again for the first time, what would it be and why?
If you could live in any country, where would you live?
If you could choose two famous people to have dinner with, who would you choose?
If you could be an animal, what would you be and why?
If you could trade places with anyone in the world, who would it be and why?
If you were going to change your name, what would you call yourself?
If you had a personal assistant, what would you delegate to him?
If you could instantly become an expert at anything, what would it be?
If you were guaranteed anything (other than money), what would you choose?
If you had to teach one subject, what would it be?
If you could learn any language (other than English) instantly, what would it be?
If you could become immortal, at what age would you stop aging and why?
If you were on a reality show, which show would you choose and why?
If you could eliminate one thing from your daily routine, what would it be and why?
If you could go to Mars, would you go? Why yes, why not?
If you could teleport right now, where would you be teleported to and why?
If you could write a book that was guaranteed to become a bestseller, what would you write about?

Basic life areas and trust

First, let's look at those that can help you determine whether you should seriously date this person. Or your ideals are too far, and you should look for another person. These questions examine the basics of worldviews and personal beliefs.

“Do you want to have children?”
“If yes, how much?”
“Do you think both partners should build a career?”
“What kind of future do you dream of?”
“Have you ever lived with anyone?”
“Tell me about your first love?”
“Do you believe in God or a higher power?”
“How do you feel about your family and friends?”
“Do you like pets?”
“How important is your job to you?”

“Tell me about your biggest life goals.”
“What really irritates you and can make you angry?”
“Are you an evil person or a good one, what do you think?”
“What would you prefer - call or write?”
“How do you like to celebrate holidays?”
“What city would you like to live in?”