250+ Questions to ask a guy (very deep and meaningful)

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By: Naveen B

Are you a curious girl, looking for some deep connection with a guy. You are in the right place. 

Here is a great list of questions to ask a guy on different topics. This huge list of a variety of questions create a good conversation starter to know your person better and have a meaningful life.

Some questions are funny, some are deep and interesting. 

By reading the full list of these questions by the end you will begin to understand the psychology of men and guys. You will understand what boys want from girls and from life.

So, take your own time to read and have good understanding about life.

Related: Serious relationship questions are answered with utmost honesty

Questions to ask a guy

  • Have you figured out the life you want to live?
  • If you wish to possess supernatural power what would it be?
  • What is that you are most passionate about?
  • What are you most proud of so far?
  • Are you interested in arts or sports?
  • Are you too serious about life or just go with your instincts?
  • Do you have any regrets as of now?
  • What are your expectations of everything?
  • How do you make decisions in life?
  • Do you everything in ease or do you struggle to start?
  • What are you most afraid of?
  • What kind of girlfriend or partner, you dream of?

Questions to ask guys about girls

Do girls’ bodies and figures really matter to guys?

What are your thoughts about feminism?

Do you support your girl in her choice of lifestyle?

How do you describe girls or women in 3 words?

What suggestion do you wish to provide for girls who feel insecure about themselves and their bodies?

Do guys think that girls are against men who are not supportive for their freedom of speech?

What is the major conflict between girls and boys? Is society created a bias in gender equality?

Why do guys take advantage of their masculine power over weak and innocent girls?

Do you change yourself completely in a good way for a girl you like?

Is there any girl in your life who changed your perception of life and made you a better person?

If you had a chance to live one more fresh life would you choose to be born a female?

Who is that one special girl you are super proud of having in your life?

Who is more intelligent girls or boys? Is it really matters?

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


Questions to ask a guy to get to know him

What do you believe in the most?

Are you missing something in life?

What are the major mind shifts you experienced over the last couple of years?

What do you consider yourself – an extrovert or an introvert?

As you guys do you have any questions to ask a girl?

What was your childhood like? Do you have any dark past or everything was smooth?

What was your childhood dream?

What is your current dream in life?

What is a love mean to you?

Do you have any crush on someone, or any ex-girlfriends, or else do you have any permanent committed relationship?

What are your top 10 favorite lists from all things in life, from movies to your rarest memory?

What makes you unique from other guys?

Where do you live? With your parents or alone?

How many siblings do you have? How often do you guys go to parties?

What are your future plans?

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

questions girls are afraid to ask guys 250+ Questions to ask a guy (very deep and meaningful)

Questions girls are afraid to ask guys

Did you have s#x with any other girls before? Are you still a virgin?

What is your honest opinion or harsh judgment on the current generation of girls or women?

What is your approach to making a shy girl become comfortable with you?

Is it okay for you If girls choose not to have any intimacy or s#xual relationship until marriage?

Do you have any insecurities about yourself and how do you overcome them?

Are you a protective guy or you are free to allow your girlfriend to hang out with any guy or with her guy friends?

What are your s#xual fantasies?

Are you a hopeless romantic man or not that much interested in romance?

What you don’t like about girls in general?

What is your ideal partner looks like?

Do you like if girls wear short dresses in public and make-up too? Express your perspective.

Do you have any physical or mental weaknesses?

How fit are you in healthy way over all?

Have you ever touched women?

Are you comfortable having s#x when a girl is in her periods?

What’s your pen#s size? Don’t worry, it’s okay for girls if you have a normal size too.

How many times do you think of s#x during the course of 24 hours?

Also read: 100 Trap questions to ask your boyfriend (Persuasive and Funny)

Flirty questions to ask a guy

Did anyone ever tell you that you look so cute and handsome as well?

Have you ever thought of me randomly?

What are the secrets of your style and looks?

Can we meet on weekends to have a party?

On what kind of dresses do I wear do you find me attractive?

What are the sensual pleasure spots in your body?

Can you save yourself for me for my whole life?

Shall we play a truth or dare game?

Do you like hugs or kisses?

What did you think of me when you first saw me?

Can you express yourself in writing form and write romantic poems about a girl you dream of?

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

Good questions to ask a guy

Who is your greatest idol in life?

What inspires you to do great things?

How does perfection exist in your own vision?

Do guys are superior to girls?

How to deal with someone who hurt you emotionally?

Do you have any plans to change the corrupted systems in society?

What are the important lessons you have learned so far in your life?

Did education ruin our dreams and future?

Why celebrities are so overrated?

What do you see in the future of our younger generation?

Do you have any personal agenda in life that you want to impact on the majority of innocent lives?

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

Deep questions to ask a guy

What do you think of religion, spirituality, science, philosophy, and art?

Are politicians, evil influences on society?

What are your darkest desires?

How deep do you think and feel about everything in life and love?

What is beauty mean to you intimately?

What is your unique philosophy about you?

Are you a mysterious guy?

What is the purpose of humanity?

Is entire mankind doomed to suffer?

How to protect humanity from humans?

How vast is this cosmos?

What kind of monster or master this so-called God is?

Are you god?

Also read: 200+ Trippy questions to ask others and yourself about life, world and existence

Questions to ask your crush

How does an Ideal woman fit in your perception?

If suddenly a girl impresses you and comes with a marriage proposal will you accept?

Do you believe in love at first sight?

How long do you think it takes a guy to fall in love?

What comes to your mind when you first look at a s#xy girl and a traditional girl and whom do you attract?

Do you have a crush on any person in general, but not celebrities?

What something in girls makes you vulnerable?

Why do love happens in a mysterious way to special kind of people?

Has anyone ever told you that you are so special and just your presence makes everyone’s life better?

What’s your favorite go-to place for vocation and especially for the honeymoon period?

Also read: 250+ Conversation starters for your online date

Dirty questions to ask a guy

How often do you watch p*rn videos?

How dirty your mind is when you are around girls?

Do you like a girl with more facial hair?

What turns you on and becomes a beast in bed?

Have you ever smelled the panties off any girl?

Do you love to lick a woman’s underarms?

What’s your reaction would be when you look at a n*ked girl from very close?

Can you gift lingerie to your girlfriend?

Have you ever peed in a swimming pool?

Do you like dirty-minded girls and h#rny women?

Mostly you get attracted to which gender?

Also read: 50 Relationship questions to ask your boyfriend (Deep & serious topics)

Funny questions to ask a guy

What are the funniest moments in your life?

If you have no legs would you walk with your hands?

Do you like the smell of your body?

How thick is your middle finger?

What kind of movies you would like to watch when you were drunk?

Will you love a girl with less brain, but a big heart?

When is the last time you remembered nothing?

How funny are you with the people you love?

Have your parents caught you while you are doing some nasty stuff?

How many girls’ numbers did you save on your phone?

Questions to ask a guy you like

What kind of people do you hang out with?

How foodie are you? And what’s your favorite dish of all time?

What do you do when you feel alone?

How many friends are there in your life?

Can you introduce me to your parents?

What kind of topics you would like to discuss with me to get to know me more deeply?

Did you ever get feelings for me?

Why can’t I help myself to walk away when you are near to me?

Will you spend more time with me today?

Who is the one person in your life you have very intimate and special feelings for?

What’s your love language?

Do you think we make a perfect couple?

Questions to ask a guy to get to know him deeper

What are the scary things and best things you do when no one is watching you?

Do you consider yourself a weird and crazy guy?

How many lives did you impact so far?

What is your greatest inspiration?

Why do beautiful people suffer most?

Are you a wise or intelligent person?

How much patience do you have with short-tempered people?

How many people have you removed so far from your life and why?

In past or at present do you have struggle with any mental health issues?

Do have any secrets in your life and whom do you like to share them with if you have an opportunity to do so?

Whom do you adore, admire and love for who they are?

Have you ever told them how beautiful they are from the inside out?

Will you stay as a bachelor or marry when you meet the girl of your dreams?

Are you a deep thinker or deep feeler?

On what occasions do you cry and what do you feel when you make yourself vulnerable in front of others? 

Random questions to ask a guy

Are you a fan of politics? 

Do you wish to become a celebrity?

Do you have any desire to get to know any random person?

How many millions make a billion?

What is life?

What is love?

Is Elon musk going to be a villain for humanity?

Have you ever tried something different in life?

Do you think humanity going in the right direction?

What do you want to change that no one ever can?

Personal questions to ask a guy

What kind of support do you need to achieve your goals?

Are you a materialistic person or kind of a monk?

What is your greatest fear?

Are you a lonely person? or a social nerd?

What are your intentions before you begin to do anything?

What are the things you wish to do now so that you can change your personal life and others as well?

Do you believe in heaven or hell stuff?

Are you a believer or agnostic?

Do you keep yourself reserved and lead a private life or show off all the things you do in life?

What do you don’t like about yourself most?

What are you seeking?

What are your thoughts on inner peace?

Questions to ask a guy over text

How was your day?

Are you free to spend a little time with me?

Shall we plan to go for a long walk?

Are you in the mood to go for a night show?

Can you play an online game with me if you are free?

Do you think I can be helpful to you when you are in need of something?

What’s your favorite anime movie?

What’s the best thing you have done today?

How are you feeling?

Do you like to have conversations over text, phone calls, or video calls, or in person?

Where shall we meet when we are done with our work?

Do you have any special surprises or plans to have date night for this weekend?

Interesting questions to ask a guy

What is the most heartbreaking moment in your life?

As a guy what are the interesting things you do when you and a girl are stuck on an island for years?

Are you interested in science? If so, Is it really a good idea to terraform mars and shift humans there?

As we grow old why does life become difficult to deal with?

How long a human spirit can exist in this cosmos even after one dies?

Is happiness the ultimate goal?

Have you ever experienced Déjà vu ?

Who controls your mind?

Have you ever felt different, in a unique and unearthly way?

Who do you think is the most conscious person in the world?

Juicy questions to ask a guy

How excited do you get when you found the love of your life?

Do you live a life full of moments and magic or regrets and hate?

Have you ever made a first move to take a girl out for dinner or for a movie?

What is the one thing you wish had never done in life?

If you have any juicy questions to ask, can you ask me freely?

How would you know if your crush has a crush on you?

What questions to ask to know whether your crush likes you?

How often do you get wet dreams?

Have you ever thought of living forever?

Do you get h#rny when you see a beautiful and pretty girl?

S#x questions to ask a guy

At what age do you have s#x for the first time?

Can you have s#x with any random girl?

Is love without s#x not love at all?

What is s#x for guys in general?

How romance is different from s#x?

What is your favorite s#x position?

Do you love to have s#x with multiple partners at the same time?

Who has more s#xual desires for boys or girls?

What’s the most dangerous place you ever had s#x?

Is s#x before marriage a taboo?

Why do men are mad over b##bs of women?

What’s your best s#xual experience so far if you had any?

Would you rather questions for a guy

Would you rather wish to stay young forever or choose to grow old and die?

Would you rather be single or fall in love?

Would you rather be a gentleman or be a pervert with random girls?

Would you rather spend your whole life working or travel the world freely?

Would you rather be a human or become a god if you had such power?

Would you rather smile at a person who hurt you or defend yourself go for a fight?

Would you rather be in this moment and enjoy life or constantly worry about the past and future?

Would you rather be a lover or a friend?

Would you rather choose to be a stranger or be famous?

Would you rather be yourself and avoid drama or seek attention, to make yourself feel good?

Questions to ask a man

How mature are you emotionally and mentally?

Are you a man of women or a gentleman for those who are in need?

What makes men different from women hypothetically?

What is morally right religion or science?

When do poverty and war between humans end?

Why do children’s life majorly depends on how parents treat each other?

Are we anywhere near to the truth?

Why do people hate and envy those who do better than them?

How to stop the negativity in our own minds?

As a man, what is your part in changing the world to be a better place?

Questions to ask a guy friend

Are we better as best friends or more than that?

What do you think of friends with benefits?

A girl is better with other girls or with guy friends who are super supportive?

Do you get jealous If your girlfriend talks to other guys?

Have you ever been attracted to your female best friend?

Why do you think girls are easily attached to guys who care for them emotionally?

What makes a girl and guy relationship perfect?

Which is better platonic love or romantic love?

Why does an emotional relationship be more powerful than s#xual relationship?

How long does it take to get over a breakup?

How to find the right partner for lifelong relationship?

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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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