250 Personal Questions To Ask for deep and meaningful conversation

By: Naveen B

We’ve all done it: We try to strike a conversation with someone new.

Either we talk about the weather, tell them about our job, or ask them questions directed towards their personality like “What’s your favorite color?”

This can be a great place to start building a connection with someone you just met. 

What if there were deeper questions you could ask on the first date or get to know someone better?  Questions that are deeper than that? The best way to get to know someone deeply is by asking personal questions.

Also read: 250+ Nonsense Questions to ask and think about (funny & weird)

Imagine you could discover someone’s innermost thoughts and feelings. Your words can have powerful effects on others.

The right words at the right time can change their lives for the better.

And that’s exactly what you want to accomplish when you’re dating, networking, connecting with clients and co-workers, or simply making friends build trust in your relationship.

To start a good conversation requires good persuasion skills and confidence to communicate your thoughts effectively.

Some people may shy away or simply do not find words to keep their conversation going. And then feel awkward and think, what do you say next?

Making conversation with someone is a great way to get to know them. It should be engaging and exciting. You might even spark a meaningful relationship.

But what questions should you ask? Do you stick with the mundane questions most people ask or do you try to dig deeper and find out why they think the things they do?

Here is the best list of personal questions to ask in many situations to different people you want to connect within your personal or professional life. Continue reading to build your communication and persuasion skills.

Related Trivia Questions: 300+ Deep Questions to ask on 50 topics

Personal Questions


Personal Questions to ask

List of best personal questions to ask to be the part of conversation starters world

What is one thing you would like to have changed parents’ life?

Do you think everything in life is so private and personal? Even the questions they ask themselves?

How healthy and important do you think one’s individuality is?

How much do you think your friends impacted your life?

Who is your favorite person to spend the rest of your life with?

Have you ever deeply changed someone’s life for the better?

Do you think we are all lonely people?

Can you briefly describe your personal life in a single sentence?

What often really hurts you?

What is the most influential advice you have ever received? And what changes had occurred in your personal life?

Who is the most innocent person in your life?

How many people you have door-slammed from your life so far?

Also read: 200+ Trap Questions on different topics


Deeply Personal Questions

List of deep personal questions which are deeply hard and intellectually stimulate you in your discussion.

When we die, how do we know that we are dead?

Do you have any memories of when you are in your mother’s womb?

How deep a thinker are you? 

What are universal values and what is your personal truth?

What personal questions do you want to ask a deep girl?

Do you prefer to feel deeply or ask deeper questions about everything?

How long can you make yourself stay alone without talking, seeing, or contacting anyone?

Who are you? Whom do you think you are?

Do you think too much or feel your emotions so deep?

What do you prefer to do when you are with yourself and not caring about world?

What’s your biggest dream in life?

Did you find your purpose and meaning in your life?

Who is the most insightful and deep person you have ever met in your life?

What’s the best and craziest idea you dream about?

Do you think you really exist now?

What does this life mean to you?


Personal Questions to ask a guy

List of dirty questions and uncomfortable and really personal questions to ask a guy.

Are you a guy who loves lonely life?

How do you find out who is the right girl or woman for a lifelong relationship?

Why do most guys are so bad, dirty, and flirty with girls?

If you had a chance would you live forever?

What makes you fall in love with a woman?

How patient are you with the pace of your life, goals, and uncertainty?

How many girls have you been dating so far?

What’s the most important life lesson you have ever learned the hard way?

Can you share the name of your childhood sweetheart?

Have you ever loved someone who is already in love with another?

Do you need people in your life in order to feel happy?

Also read: The best collection of Icebreaker Questions you’ll ever need


Weird personal questions

List of weird questions to ask. These are very interesting personal questions to keep you engage in the conversation for a long.

How often do you punish yourself brutally without any mercy?

What is the weird thing you ever tasted in your life?

Why do you like weird questions? Have you ever asked yourself in a funny way?

Do you like to be a god or a human forever?

What color is your undergarment? Hmm..! So, nasty and weird question?

How seldom do you have the habit of taking bath?

Do you ever wash your hands after coming from the washroom?

Did you ever smell your own sweat? Have you tasted it? Did you like it?

How many people you have slept with so far?

Why are you so weird and socially awkward?

Have you ever realized your own ignorance?

Also read: 500+ Get to know you questions

Personal questions to ask a guy dirty

Here is a list of dirty questions to ask a guy. Very personal questions.

What is the most terrifying location ever where you enjoyed having s*x?

Have you ever peed in your pants during your adulthood?

When is the last time you did mast**bation?

Do you meet your ex-girlfriends regularly?

Why do men don’t have vagin*s?

What’s your favorite body part of women?

With how many girls had group s*x ever?

Did you ever have feelings toward your own siblings?

Which gender are you most attracted to?

What part of the women’s body makes men go crazy?

At what age do you lose your v*rginity?

Can you explain to me in detail, how you feel when you sleep with someone?

How long can you control your s*xual needs?

Also read: Deep Intellectual Questions to ask to get to know someone better


Personal Questions to ask a girl

List of personal questions to ask a girlfriend or a girl to spark a deep conversation.

What ignites your soul?

What does self-love mean to you personally?

What are your psychological vulnerabilities?

What do you think you do better than the rest of the girls?

Were your childhood life experiences blissful or completely suffering?

What is the one personality trait you carried throughout your life?

What’s your favorite memory of your teenage?

What is the hardest thing you have ever done so far?

Have you ever felt ashamed of being the way you are?

Did your parents ever worry about your future?

What do you do all the time in your free time?

What do you think about men and guys?

Do you have a secret crush on any person?

Who is the one person who understands you completely even without expressing yourself?

Do you believe in god?

What makes you move forward in life irrespective of its difficulties?

Related: 350+ Questions about love that makes you think.


Questions to ask guys about girls

List of questions to ask men about women. Personal questions to ask a guy about relationships to know him deeply. These list of questions to ask are very intimate and insanely deep.

What is the one best quality in a woman that makes her perfect?

As a guy what do you think about girls who are very open type?

Do girls and women are equally competent as men?

What is the most popular love language of girls as per your observation?

What is your opinion on relationship between younger men and older women; older men with younger girls?

What are the top sexiest features of girls?

Do girls are more intelligent and wiser than guys?

How long does it really take for guys to propose to girls?

How many types of girls are there in this world?

What is the one thing you believe about any girl that is absolutely true?

Who is your dream girl or ideal woman?

What is the perfect job for girls?

Why do you think that there are very less world women leaders when compared to men?

What’s your perspective on the world, is society controls women?

If you had a chance to open up what personal questions do you want to ask about girls?

Also read: 75+ Tricky Love Questions to ask your boyfriend or girlfriend

questions to ask to get to know someone 250 Personal Questions To Ask for deep and meaningful conversation

Personal Questions to ask to get to know someone

Personally, do you really want to know someone deeply? Then Try asking these deep questions which are really very personal that connect you with them and strengthen your bond.

Here is this list of personal questions to get to know someone.

What do you think people think of you? Do you really need to know what people talk about behind your back?

How far do you think you have come in your life’s journey?

Is life a lonely path? 

Personally, how many friends do you think are real to you?

Do have any second opinions on people you don’t like?

What makes others attracted to you?

Do you have more friends or enemies?

What is the most painful event in your life?

What’s your life story? Is it sad and inspiring; or happy and boring?

How do you respond to the people who betrayed your trust?

What connects you to the mother nature?

Do you believe in true love?

What makes a person achieve greatness in one’s life?

Also read: 900+ Questions to ask people (huge list of topics for deep conversation)


Personal Questions to ask friends

List of personal questions to ask your friends. Most personal questions that worthy to be asked in a debate or any conversation.

What do your friends find likable about you?

Which friend of yours genuinely care, support, and inspire you towards your goals and wishes you a huge success?

When you are in a worse situation, who came to rescue you and how?

What is the definition of friendship on your own words and realization?

How do you make someone believe in you and trust you completely?

What is the most unforgettable thing about your whole relationship bond?

Under what circumstances would you betray your own close friend?

Will you sacrifice your own life to save your best friend? Why and if not, why?

Do you choose your friends or family members or anyone to be simple or complex in their personality?

At what age do you want to marry and plan to have babies and settle in life?

Also read: 1000+ Truth or dare questions game for your next party (Good Clean and Dirty edition for friends, family, teens, couples very funny)

Personal Questions to ask your boyfriend

List of personal questions to ask your boyfriend or your girlfriend to strengthen your existing relationship and bond.

How do you measure your love towards me?

What is your first impression of me when you first saw me?

As a boyfriend do you have power on me for whatever I do?

What is your favorite s*xual fantasy?

What makes you trust me?

What are five things about me are appealing to you?

Who is a person you regret having intimate relationship with?

What are your expectations of our relationship?

How have you ever cheated on me?

Do you have any secret crush on other women or girls?

Do you think we both are ideal couples and made for each other?

What’s your darkest desire?

What is the one thing that you are afraid to ask me?

What can I do to make you happy, pleasurable and peaceful?

What kind of thoughts comes to your mind when you kiss me?

If one thing that you want a change in me, what is it?

Also read: Dating Questions 101: Conversation starters topics for online, first & second date nights

Funny Personal Questions

List of funny personal questions that make you smile, laugh, and make you serious for sure.

What is the funny thing about you people like to adore?

Personally, do you think are you a fun kind of person or boring to live with?

Have you ever tasted your own (personal) stuff?

If you were a dog which brand of biscuits you love to eat?

While you are asleep and if you are in your favorite dream world, would you ever want to wake up?

Which side of your body looks ugly and which side of your face looks like dumb?

If you want to sue anyone’s life, who would it be?

Would you marry a person whom you hated all your life?

Will you ditch a person after you used them completely?

What kind of monster are you?

Also read: 200+ Questions for couples to strengthen your bond

Personal Questions to ask someone

List personal questions about life.

Have you ever been into a Television reality show?

What is your favorite movie of all time?

What kind of childhood games you still play?

What are the 10 most crucial things you could do to better your life if you exerted the greatest self-discipline?

What is your strangest possession in your personal and deep philosophical life?

What is the one odd thing you like about yourself?

Have you ever attached to someone emotionally, physically and spiritually? 

At what age do you want to die in your life?

What is the most difficult but honest thing you carry with you?

Do you believe in pre-destiny?

What is your waking call?

Also read: 31 Deep questions to ask your boyfriend (Be evolved after this conversation with him)

Good Personal Questions

List of good personal questions to start a conversation.

Does your lifestyle constitute any profound values that your kids can feel proud of?

What is one piece of great wise quote you would share with any newborn child?

What makes a personal life choice can bring fruitful or devastating results?

Would you like to direct a story or movie on your personal life?

What type of music do you love the most?

What one existing novel or movie reflects your personal life?

Do you love to read or write or none?

Do you consider yourself a mature person or a completely confused person?

Are you a nature person or a tech person who want everything to be digitalized?

What is your greatest hobby to pass your time in the most passionate and efficient way?

Do you think you are wasting your entire life?

Also read: 250+ Conversation starters for Tinder (With best topics, openers, questions and tips)

Deep Personal Questions to ask a guy

Here is a great list of important questions to ask a guy to know him personally.

Mostly do you want to work with men or women?

What is the dumbest thing you ever did in your life?

What is the deep and scariest secret of your personality ?

What is one thing that people misunderstand about you?

What is your own judgement about yourself?

Do you have any deeply rooted morals, ethics and beliefs? What are they and do you follow them?

Are you a happy person or the deepest sad human?

What is the ultimate philosophy of your life?

What are the deep questions you want to ask but never shared with anyone?

What is the ugliest truth about yourself that you never want to share even with your girlfriend or partner?

How s*xually active you are?

Do you like suffering?

What do you think happens to everyone after their death?

Also read: 750+ Conversation starters on topics for any situation (Your ultimate questions list)


Interview Personal Questions

List of job interview personal questions to ask if you ever attend any professional interview. Take a deep look into these interesting questions and be prepared to answer to crack any exam.

What is your inner genius? Did you find it? If not, where do find your inner genius?

How do you achieve which you are not aware?

Are you a creative person? What is the source of your creativity?

How do you express the reality to a blind and deaf person?

Often, what are the most intimate and personal questions you ask yourself to bring a change in your attitude towards life?

What do you love the most?

What has ever uplifted your soul?

What has dominated and delighted your spirit to choose the life you want?

What makes you really happy? and how do you spread that happiness on others to change their lives too?

What is the leading position you want to take in the type of work you do?

How do understand the essence of human desires and emotions?

What societal rules influenced on how you think about the world and this existence?

Also read: Huge list of 650+ questions that make you think (on different topics & concepts to ponder)

Personal questions to ask a guy over text

List of personal questions to ask a guy over text. Even you can ask the same questions to ask a girl over text.

Have you ever texted your ex girlfriend/s?

Are you comfortable with online chat, texting, video calls, or talking for real in person?

What are your core principles in your personal life?

Do you believe in dating sites, online relationships, or long-distance relationships?

 Are they reliable and works for a decent girl or a boy?

What is something you regret and wish that you never did in life?

Are you a passionate lover? 

Have you ever thought about having the life you dreamt about?

What do you envision yourself to become when you grew up?

Who are your inspiration in life?

How different are you from other guys?

Which novel, movie, or character had a major influence on the way you think?

Would you change your childhood if you had the persona superpowers?

Also read: 1000+ Random Questions (The only list you need to ask for deep conversation)

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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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