250 Questions to ask right now to understand anyone

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By: Naveen B

We are all curious to know what people are up to. Especially, those whom we like, admire and attract.

Sometimes we find it very difficult to break the ice and have a comfortable conversation. 

Initiating a discussion is an art of communication. But that shouldn’t be hard. There are different ways to create a first impression and build relationships. Mostly it begins by asking the right questions.

Questions are the simplest way to get to know someone. They provide a glimpse into the other person’s world and reveal the type of person they are. 

Even that applies to our own selves. The right questions to ask for self explore and discover true inner selves.

Have you ever asked yourself questions no matter how funny or no-brainers they are?

How often do we find ourselves speaking to someone without asking the basic questions that could get us to know them better?

We’re so preoccupied with our own lives and schedules, that it becomes difficult for us to find the time to ask these questions and start conversations that matter.

Elie Wiesel an American author and Nobel Laureate once observed: “People are united by questions. It is the answers that divide them.”

Many “answers”—in fact, they are just opinions pretended to be “truths”—seem to be dividing us more than ever these days. And yet, we still have a deep need and a powerful need to connect with others.

No wonder! If you are here means, by instinct, you feel exactly what this author has observed and concluded. 

We all ask questions. It’s what we do to get to know people, and sometimes it feels like the question is more important than the answer. We all need to ask questions to ourselves or to others in order to learn or to connect with others deeply.

So, why to wait, I have put some effort to write a huge list of questions to ask to get to know anyone you like.

Take your time and have a deep dive into these great questions that make you think.


Good questions to ask

Here is the list of good questions to ask a girl, a guy, your friends or someone you like.

  • Is nothing something?
  • Why do I sometimes feel lonely and that no one loves me?
  • How do you know if someone is a real friend?
  • How can I remain calm when I see so many bad things in the world?
  • What do you do when you are scared?
  • Why are there good days and why are there bad days?
  • Why does my mind occupy with deep questions?
  • Why do people make wars if everyone’s goal is to achieve peace?
  • I’m having a problem with someone, but I’m too shy to speak to this person. What do I do?
  • Why does the world exist?
  • How to love someone who likes different things than you?
  • What should you do if someone feels bad and you want to comfort that person and make him or her feel better?

Related: List of Deep Questions on life, love, relationships to ask your boyfriend, girlfriend or someone you care.


Funny questions to ask

Here is the list of hilarious and funny questions to ask. As kids, we are full of life, fun, and curiosity in our minds. The questions we ask are strange but deep. 

No matter how old we grow, some questions always bring a smile to our faces.

Enjoy reading these funny questions and you can ask these random funny questions to friends, to people you know, or to any girl or a guy and laugh your heart out.

  • Where do babies come from? Did I come out of the belly button? Did a stork bring me to earth? How did I get born?
  • Why does he have a penis, and I don’t?
  • When you grew up, did you want to be a mommy/daddy?
  • What we were doing when we didn’t born?
  • Why take a bath again, if you have taken it yesterday?
  • Why aren’t we in our parents’ wedding videos? Are we shooting their pictures and videos?
  • Do dead people watch us?
  • Does God use an iPhone or surf the internet when he gets bored?
  • Where do we go after we fall asleep?
  • Does money grow on trees?
  • If I eat my cereal, will I be a good soccer player?
  • Why do some people have brown (or white) skin? Why are some people fat and some people thin? Why does that person have different eyes?

Relationship questions to ask

A relationship is all about sharing personal issues and happy moments. Marriage is not an easy concept. However, it is rewarding if understanding people stay around us.

I have written a few relationship questions to ask a guy, or girlfriend, or a friend or partner committed relationship about the future, to improve the depth of the bond in order to make your life better. 

These are the list of family questions to ask about relationship problems and questions to ask about love.

  • Why are our most challenging relationships with the people with whom we are closest?
  • When a relationship ends, my feelings of sadness, anger, and jealousy last for weeks and even months. How can I turn the page on these painful feelings?
  • How can we ensure that our home lives remain peaceful even when the world outside is not?
  • A loving relationship should be made up of two equal partners. How can we ensure that the stronger of the two does not overpower the weaker one and swallow him or her?
  • How can we raise our children to be more mindful and compassionate?
  • Some people say that mothers who work outside of the home don’t take good care of their children. But what if a woman stays home and still doesn’t pay much attention to her children? How can we parent while still doing the other things in our life that require attention?
  • I had abusive parents and I’m still very angry with them. How can I avoid passing this anger on to my own children?
  • How can those of us who had a painful childhood get past our pain and learn to trust people again?
  • I’ve been caring for my elderly parents for several years. I love them, but it’s a financial and physical burden, and I’m finding it more and more difficult. What can I do?
  • I’ve been practicing compassionate listening but it is very difficult to listen to people who rant and rave. How long is it necessary to practice compassionate listening?
  • My mother-in-law is very critical. I try to be tolerant of her, but sometimes I get exasperated. What will change this?
  • My father and I had a difficult relationship. We could not talk or listen to each other, and now he is dead. Is it too late for us to find reconciliation?
  • How can we influence members of our family who aren’t interested in spiritual practice or teachings, but who spend a lot of time indoors watching television and eating unhealthy food? 

You may also like to read: 350+ Questions about love that make you think


Questions to ask yourself

Here is the list of deep questions to ask yourself every day or in the future to get know to yourself and find out who you are.

These are self-reflection questions that help you to discover your true self.  These personal questions are a bit spiritual and most important as they play a crucial role in your self-growth.

  • Who am I?
  • What are my top five personal and professional values?
  • How am I living outside of my values?
  • What do I fear the most?
  • What fears have actually come true in my life?
  • How do my close friends and family view me?
  • What are my greatest strengths and weaknesses?
  • What beliefs am I holding on to that are no longer true for me?
  • How am I living a lie or living inauthentically?
  • Do I have shame or guilt that needs to be resolved?
  • What am I doing to further my personal and/or spiritual growth?
Questions to ask a guy 250 Questions to ask right now to understand anyone

Questions to ask a guy or boys

Good questions to ask a guy you like or you just met to get to know him over text and ask his opinion about girls in general.

You can also ask personal or interesting questions such as his philosophy of life and start a deep conversation to break the ice. 

If you like his answers, there is the possibility of strengthening your bond in the future.

Read this list of questions to ask boys or a guy friend. You can ask just for fun or with deep meaning. If you are a fun type you can ask dirty or flirty questions too, just to know his reactions.

  • What is this life means to you?
  • What makes you, you?
  • Do you have friends?
  • Are you an extrovert or an introvert?
  • What’s your childhood favorite memory?
  • Do you have any childhood crushes?
  • What are your dreams and aspirations?
  • Have you ever kissed any girl?
  • What are your dreams and aspirations?
  • Do you believe in love at first sight?
  • What are your expectations of yourself and from the people you care about?
  • Why do you think life is so unfair?
  • What are your most pleasurable moments?
Questions to ask a girl 250 Questions to ask right now to understand anyone

Questions to ask a girl

List of interesting and good questions to ask a girl to get to know her better.

Make her smile, laugh, over chat or by text with flirty, funny questions, and strengthen your bond deeply genuinely. Just be thoughtful and at the same time romantic, girls truly love that.

  • How do you see your opposite gender?
  • How comfortable are you sharing your emotions and feelings to a guy you like?
  • Which characteristics do you love most in a man’s personality?
  • What is an ideal man according to you?
  • What’s the most influential book you ever read?
  • Who is your inspiration?
  • If an evil person and a good person are in danger, who would save if you have the opportunity? Explain with a reason.
  • How many chances do you give to a person who hurt you knowingly or unknowingly?
  • Have you ever door-slammed anyone? Why and why not?
  • What’s your dream job?
  • What are your thoughts on social media?
  • What are your favorite topics to talk about?

Questions to ask your crush

If you don’t know how to talk to your crush, just take a long breath and start the conversation by asking random questions. Try to ask a mix of deep, fun, and flirty questions.

Here is a great list of random questions to ask your crush.

  • What makes the moon shine brighter than your face?
  • What tips would you give to others to maintain such beauty and charm as you?
  • What’s the best way to convey that you love someone?
  • How many people proposed to you so far?
  • What qualities in a person make you attract them?
  • I really admire the way you express yourself and present your personality, What’s the secret behind such incredible talent of yours?
  • I think I have huge crush on you, would you mind sharing more about yourself. I am really fascinated by your brilliance, beauty, and kindness?
  • What kind of movies or genres of books do you love?
  • Do you have particularly any go-to person in your life? Hope he or she is an ideal person, would you mind introducing me to them? I am curious to learn from them too.
  • What’s something weird you find attractive?
  • What kind of people do you like, is it flirty, dirty, nasty, weird, thoughtful, or all of these qualities?
  • Would you accept my invitation for a cup of coffee, this evening? I would like to honor my time with you?

Personal questions to ask

List of personal questions to ask a guy or a girl to get to know them and bond a friendship.

  • What are the most important life lessons you have learned so far?
  • What is the best and worst piece of advice you ever got?
  • Who is the last person to who you are deeply connected but he or she doesn’t know?
  • Which book do you recommend to the people who are so reserved and deeply personal?
  • What is something people get wrong about you?
  • How do you approach a person who has completely opposite beliefs to you? How do you talk to them?
  • Who is the person you think has had the most profound effect on society in the last several decades?
  • What is your personal proudest accomplishment?
  • What happens when you die?
  • Do you fear death?

You may also like to read: Huge list of Questions 50+ topics that make you think better

Questions to ask people

Generally, we can’t read people’s minds exactly. So we just assume about their personality.

We may be right or wrong in our judgments, in order to avoid such conflicts – in psychology, there is a concept that when you don’t know what people are up to, then you have to persuade them by asking questions consciously.

Read this list of deep, interesting, random, and good questions to ask people to get to know them which may help you to improve your cognitive and critical thinking skills.

Do you mostly see the glass as half empty or half full?

What are the most passionate things about this life that make you feel alive?

What are your personal powers?

What can we learn from a 3-year-old child?

How do we know who are our enemies and friends?

Why do people suffer and struggle in life?

Do we all need a reason to wake up?

Do we all have a purpose in life?

Who is the happiest couple in the world?

What is enlightenment? Have you ever achieved that state? Why, why not?

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Questions to ask friends

Friends are the only buddies whether it is boys or girls, they know our darkest secrets and weakest strengths. 

Apart from having fun, sometimes we have to be serious in life to get to know more about ourselves in order to excel in any career path. In every group at least there will be one friend who sees beyond. 

You can approach and ask questions to your friends to give feedback and to know yourself better. At the same time, you can ask them questions to know their true potential.

Here is the list of questions to ask your friends.

  • What do you think are the true qualities of friendship?
  • What is the best approach to deal with misunderstandings or conflicts between friends?
  • What do you see in me as a person that creates respect and trust for me?
  • Do you think we become a great business partner?
  • How is our friendship different from others as far as your experience with me?
  • Do you have any suggestions or advice for me to improve my personality (weaknesses or strengths)?
  • Will you ever forgive a person who unknowingly or knowingly hurts you?
  • Who do you think understands you more, a family or friends?
  • Why do smart or intelligent people have very few or no friends at all?
  • Which relationship is more important to you friendship or love?
  • Can a male and a female ever be friends for their whole life?

Interesting questions to ask

List of interesting questions to ask someone.

  • Why do you want to feel good all the time?
  • Why is there something rather than nothing?
  • Is every human being seriously depressed personally?
  • Are we all alone in this vast cosmos?
  • How to solve life’s problems with the right mindset?
  • What is to be a great leader?
  • Does every person on this earth is beautiful?
  • What if we do not believe in ourselves?
  • Is everything connected to everything else?
  • What makes life worth living?
  • Why do people suicide?

Random questions to ask

List of random questions to ask someone you know or when you get bored and have fun for a while by taking a break in your busy schedule.

  • What do great scientists and philosophers think about the most?
  • Who is the wisest woman or man on this earth?
  • How can one completely trust someone?
  • What random things come to your mind when you are alone? 
  • Have you ever stared at a stranger so that he or she lost control and punched you in the face?
  • Other than gentleness what is that you most attracted to?
  • What would you do if you become an animal for a day?
  • Do babies bear with wings?
  • Do you consider yourself as intelligent or stupid and childish who annoys your neighbors?
  • What do you think that people think of you as general? Does it matter? if not, why?

Questions to ask to get to know someone

In this list, you’ll find some of the most natural and thoughtful questions to ask to get to know someone new and build a connection with them.

  • Do you think of yourself special or average person?
  • How often do you wander about everything in your head?
  • How many friends do you have?
  • What will you do when you see a helpless person?
  • Do you like to travel or just choose to enjoy your own company in your room?
  • How do you describe the beauty and what does it means to you?
  • What do you see in a person that makes you attracted to them?
  • Will you ever be single or committed?
  • What are your thoughts about this life and the world in general?
  • Do ever felt like no one understands you?
  • Are you a happy person or do you feel it is okay to have suffering in life?

Stupid questions to ask

List of stupid questions to ask just to make the conversation funny.

  • How honest are you? Would you prove it without doing anything?
  • What makes an animal, animal, and a human also animal?
  • Have you ever kissed your own face in the mirror? Why did you do that? 
  • Why do stupid people become so popular so easily than genius people? Meaning that the majority of the world is stupid and foolish?
  • Why don’t buffaloes bear to elephants?
  • Do babies poop in their mother’s womb when they are eating delicious food?
  • Do you think I am stupid for writing these stupid questions?
  • Why do people laugh at stupid things?
  • Do ghosts have tails and humans have no brains?

Questions to ask your girlfriend

  • What was your first opinion about me when you first saw me?
  • Do feel jealous if I talk to other girls? If so, what would you advise me to respond when they genuinely needed my help?
  • How to be happy and peaceful in a relationship? Can you be my cozy love of life?
  • What’s your favorite place to visit on this planet?
  • Do you think we make a beautiful couple together?
  • What do good parents want their children to be?
  • What are your instincts on lying, cheating, and abusing?
  • I feel most of the girls are food lovers, what’s your favorite dish?
  • What’s your love language?
  • Have you ever witnessed the greatest love in your real life?

Questions to ask your boyfriend

Try asking these questions to your boyfriend in order to get much clarity about him and his perceptions. If you need more about a man check these deep questions to ask a guy.

  • What’s your opinion on s#x before marriage?
  • How do you handle the most difficult situations in life?
  • What’s the best approach to lead a beautiful and better life?
  • What’s your philosophy on living a peaceful life?
  • Are you a spiritual or scientific guy or both?
  • What do you believe in the most?
  • What are your thoughts on being single and to be in a committed relationship?
  • What are your values, morals, and ethics in your life and how do you reflect on them?
  • Why do you think people divorce even after they love truly?
  • What is love mean to you?
  • What’s your ideal relationship partner?

Questions to ask before marriage

  • Is it comfortable for you to have s#x before marriage, or shall we wait until marriage? 
  • Do you think we are ready for the next step in our relationship?
  • How to convince our both parents that we are perfect for each other? Do you have any best idea or approach to make our love successful in marriage?
  • What’s your opinion on breakups and divorce? How to stay together and avoid conflicts in the future?
  • What are your emotional triggers, what can we both do to comfort each other during our existential crisis?
  • Shall we plan for children soon after we get married or shall spend time together to get to know each other better?
  • How many children do you think it’s best to be planned?
  • Can you sacrifice your life for the people you care about or for your family?
  • Do you think am I your ideal partner?
  • How to make each other better in our personal, relation and professional lives

Serious questions to ask your boyfriend

  • Are you ready for marriage or are you secretly being forced into it?
  • What are your views about arranged marriage?
  • How is your relationship with your parents?
  • What do you think about faith and religion and spirituality and science? Which do you believe in more? And share your views on each one of them?
  • What are your financial plans for the future?
  • What qualities do you value about yourself most?
  • How do you conflict or fight when they come up?
  • What qualities do you value most in other people?
  • Who do you miss the most in your life?
  • What was the most painful event in your life that changed your perspective about life?
  • What is the most serious secret that you never disclosed to anyone yet and are you comfortable to share with me?
  • Do you think we are really perfect for each other?

Weird questions to ask

Here is the list of weird questions to ask that make you think.

  • Would you like to be a human or an alien?
  • Why do hippies have a unique sense of happiness in life?
  • What do you do most of the time when no one watches you?
  • If you don’t want to see any humans anymore, where do you live the rest of your life all alone?
  • Why do you live, when you are going to die anyway?
  • What you can’t do without starting a fight?
  • When will teleportation happen?
  • How many ants will make an elephant?
  • Have you ever told your parents that you are adopted?
  • Does it take 18 months for twins to be born?

Dirty questions to ask

  • Did you keep any cute or dirty names for your private parts?
  • What do you think about when you feel so h#rny?
  • What kind of fantasies do you have about s#x and girls?
  • Would you consider friends with benefits?
  • When is the first time you felt that you are mature enough to have s#x?
  • Do you like lip biters?
  • What do you like to be called during nooky?
  • What is the wildest thing you’ve done er#tically?
  • Would you rather kiss or cuddle?

Get to know me questions

Questions to ask about self to get to know how your future self will be. Here is the list of moral questions for yourself.

  • Am I willing to be seen as naïve?
  • What is the best way to relieve my suffering and the suffering of my friends and family?
  • Am I comfortable raising questions with no immediate answers?
  • Some of us have done terrible things in our past and continue to suffer guilt over how we’ve harmed others. Is it possible to move past this kind of pain? 
  • Am I willing to move away from what I know?
  • How can I forgive people who have hurt me, without condoning them or absolving them of responsibility for their behavior? 
  • Am I open to admitting I might be wrong?
  • Am I willing to slow down and consider?
  • Am I becoming who I am supposed to be?

Deep questions to ask

Deep questions to ask a girl, your boyfriend or yourself to expand your mind and perspectives about life and love. Here is the list of deep questions, immerse in them to find yourself.

  • So far, what are your deepest thoughts about life?
  • How deep do you feel about everything when you get hurt so much by the person you once loved?
  • Will you choose silence or death?
  • Can’t we live without suffering?
  • When does everything make to everyone?
  • Why do no one rarely understands everyone?
  • What makes life beautiful and painful at the same time?
  • Is it ok for you to live alone forever?
  • Where is everyone?
  • What are you seeking anyway?

You may also like to read:

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250+ Personal questions to ask for deep and meaningful conversation.

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Question vector created by pikisuperstar – Freepik

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Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

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