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300 Questions to Ask a Guy – Your Master List

300 Questions to Ask a Guy – Your Master ListUpdated on October 7, 2020 | Published on June 8, 2020

300 Questions to Ask a Guy – Your Master List

You probably just googled “questions to ask a guy” or “questions to ask a boy

and that led you here.

Well, don’t worry…

You are not alone!

There are so many of us who suck at deep conversations. Especially when you are facing your crush and starting from a blank slate. The painful awkward silences on first dates, or the unending flirty banter over texts prevent you from discovering each other.

It’s an art to craft great conversation starters. Yet it’s so underrated that people don’t give it much thought until the D-day. Thus, end up with conversation topics like weather.

So, we have compiled a list of questions to ask a guy that will help you understand men on a deeper level. All the questions are segregated into various heads like good, flirty, personal, random, weird, etc. You can pick and choose depending on your own comfort, convenience, and mood.

So, let’s first begin with

Funny Questions To Ask A Guy

Funny Questions To Ask A Guy and Share A Laugh
Funny Questions To Ask A Guy and Share A Laugh

Because there’s no better ice breaker than a common laugh. When your toes are jittering because of nervousness, a few funny questions can ease you out. So, when in doubt about where to start a conversation, begin with these few questions:

  1. What’s the most embarrassing thing you’ve ever done?
  2. What’s your biggest pet peeve?
  3. Tell me one instance that can make you laugh almost every time?
  4. Who’s your biggest celebrity crush of all time?
  5. What is the weirdest nickname people address you with?
  6. What would you choose: No Internet Ever or No TV ever?
  7. No shower in a week or no brushing for a week?
  8. If you could only eat one food for the rest of your life What would it be?
  9. Which fictional character would you like to play in real life?
  10. If you were a girl for a day, what would you do?
  11. How would you react if a guy asked for your number?
  12. What’s a compliment you’ve ever received that looked more like an insult?
  13. If you were ice cream, which flavor would you be?
  14. Which celebrity actor will play you if there was a movie of your life?
  15. What’s the funniest movie you’ve ever watched?
  16. What’s the weirdest trend in social media you have ever come across?
  17. What superpower have you always desired?
  18. What’s the weirdest thing on your bucket list?
  19. You are asked to make insects a popular food item in exchange for a million dollars, how would you do it?
  20. What’s the most embarrassing thing you’ve ever done and got away with?

Now that you know he has a good sense of humor, move ahead to deeper conversations to take a dig into his real personality.  Here’s a list of personal questions you can ask a guy to know him better.

300 Questions to Ask a Guy – Your Master List

Personal Questions To Ask A Guy To Get To Know Him

Personal Questions To Ask A Guy To Get To Know Him
Personal Questions To Ask A Guy To Get To Know Him
  1. Do you make life decisions based on your heart or mind?
  2. Who is your role model in life?
  3. If you could be anywhere in the world right now, where would you be?
  4. If you didn’t need money or a job to survive, where would you live?
  5. What is your biggest weakness?
  6. What does friendship mean to you?
  7. What’s the best thing about being a male?
  8. What is your favorite movie you have watched 100 times over but ever get tired of it?
  9. Do you believe in Love wins everything?
  10. What is unforgivable in your eyes?
  11. How will you define your perfect day?
  12. What’s the biggest lie you have ever said?
  13. Are you a religious or spiritual person?
  14. How do you like to spend your Saturday nights?
  15. Do you like to play video games?
  16. What are the kinds of tv shows you like to watch?
  17. What is one physical feature you notice in girls as soon as you see her?
  18. If you had to listen to one song on loop, what would it be?
  19. Where would you want to live in, beach, city or mountains?
  20. You are best described as naughty or nice?
  21. What according to you is victory?
  22. What do you like and hate in yourself the most?
  23. What keeps you going in difficult times?
  24. One instance when you got trouble with the law?
  25. What’s the scariest thing you have done in life?
  26. What’s your favorite type of food to eat?
  27. What inspires you every time you hear of it?
  28. What’s one thing you would want to know more about?
  29. Who’s your favorite athlete or sportsperson?
  30. Where did you grow up?
  31. What’s the best and worst type of food you have ever tried?
  32. Do you have a phobia? What is it?
  33. What is the one thing you haven’t done in a long time but will love to do?
  34. What will you ask someone to find out the most about them?
  35. Would you rather choose Family or Career?
  36. What is your dream vacation spot?
  37. What is your favorite animal?
  38. What’s your family dinner like at Thanksgiving?
  39. Spender or saver – what are you?
  40. What do you think makes someone a hero?

After a round of personal questions, let’s add some spark in the conversation with some flirty questions.

Flirty Questions To Ask A Guy (On A Date)

Flirty Questions To Ask A Guy On A Date
Flirty Questions To Ask A Guy On A Date

You are on a date, not in an interview. You definitely wish to know this man, but not as an interviewer. Add some fun to your date with these playful questions.

  1. How was your first kiss like?
  2. Do you think I will make up for a good partner?
  3. Do you mind kissing on the first date?
  4. If you had to describe me in 5 words, what would it be?
  5. Is this date as good as you had imagined it to be?
  6. What do you tell a girl you are interested in?
  7. What is your go-to flirting move?
  8. What’s the best pick up line you have ever heard?
  9. What is one thing that instantly turns you off?
  10. How would you describe me to someone else?
  11. How do I look today?
  12. What according to you will look best on me?
  13. Will you brag about me to your friends?
  14. Do you think you are romantic?
  15. What would you do to make me relax on tough days?
  16. Have you ever skinny-dipped?
  17. If you had to describe yourself in 3 words on an online dating profile – what would it be?
  18. Have you been working out lately?
  19. How do you ask someone out?
  20. Are you comfortable with people who ask a lot of questions?

If you think it’s too much for the first date, you can let the conversation flow casually and leave the rest for the next date.

Good Questions To Ask A Guy That Will Reveal His True Personality

Good Questions To Ask A Guy That Will Reveal His True Personality
Good Questions To Ask A Guy That Will Reveal His True Personality

A guy’s personality can tell you a lot about him.

His priorities in life, choices, and preferences, or even his ethics and beliefs. Ask him the following questions and he will be forced to disclose his real self to you.

  1. Tell me about 3 events in your life that have contributed to what you are today?
  2. What is the one memory you want to remember more clearly?
  3. What’s the best advice you received or given?
  4. What is the one thing you don’t want people to know about you?
  5. What is the one thing in person you really look for?
  6. What’s the first thought in your mind when you see a homeless person?
  7. What’s the one thing you really want to master?
  8. One thing was fun to do but you will never do it again?
  9. Where do you see yourself in the next 5 years?
  10. If you were invisible for a day, what would you do?
  11. How will you earn someone’s respect?
  12. Have you ever done something nice for a stranger? Describe it.
  13. You are asked to leave the house with only one thing, what will you pick?
  14. What law would you like to change or abolish?
  15. What are you currently saving for?
  16. What’s your long-term dream in life?
  17. What’s your new resolution for this year? Are you being able to follow it?
  18. Stay-in or Go out: What do you prefer?
  19. Do you plan your day in advance or just go with the flow?
  20. Smart or handsome: If you could be just one, what would you like to be?

That’s a lot of serious discussion there.

Let’s make the conversation light with some –

Weird Questions To Ask A Guy (Awkward Questions to Ask a Guy)

Weird Questions To Ask A Guy That Will Add A Tinge in A Conversation
Weird Questions To Ask A Guy That Will Add A Tinge in A Conversation

Here are some weird and freaky questions to ask a boy that will add a tinge in a conversation –

  1. Which celebrity do you think would make the horrible leader?
  2. Which historical figure doesn’t deserve to be in history?
  3. What do you think in today’s society needs improvement?
  4. What world problem do you think is a façade?
  5. What’s the most disgusting pick-up line you have ever heard?
  6. Is there anything you want to change about social media?
  7. Have you ever cheated in exams?
  8. What according to you is the greatest invention of all times?
  9. The egg or the chicken: what do you think came first?
  10. How do you set the flap of toilet paper – over or under?
  11. What’s your go-to dance move?
  12. How many nights have you gone without any sleep?
  13. What is the one thing you look stupid while doing it?
  14. Can you do it now?
  15. If you were a pizza topping for one day, what do you think you will be?
  16. When have you been the craziest?
  17. If you are passing by a stranger, what is the weirdest thing you can say to him/her?
  18. What is the weirdest flavor combination you enjoy?
  19. Have you peed in public? Where?
  20. If you were a disease, what will be your symptoms?

A good conversation triggers all the emotions in you. It intrigues you, tickles you, and even bothers you. So, don’t be afraid to ask questions that are just for fun or even –

Dirty Questions To Ask A Guy (Sexual Questions to Ask a Guy)

Dirty Questions To Ask A Guy To Know What He Likes in Bed
Dirty Questions To Ask A Guy To Know What He Likes in Bed

Two or three dates later, when you are thinking about a stable future with the guy. What if you found out that he does not support sex before marriage? Or that he is insecure about sexual relationships?  

Thus, it’s always better to ask and clarify before you are emotionally invested.

  1. What is the favourite part of your body?
  2. What is your biggest turn on?
  3. Do you like dirty talk on texts?
  4. What is your favourite position?
  5. What do you wear to bed daily?
  6. What is the part of my body you find irresistible?
  7. Do you often have dirty dreams?
  8. Do you like girls making the first move?
  9. Have you ever bought lingerie for a girl?
  10. Have you ever been naked in public?
  11. What would you do if you were the only human alive on earth?
  12. What part of my body will you be staring at if I catch you in the act?
  13. What’s the best dressed for you: Lingerie or nothing at all?
  14. What is the one thing that is irresistible for you?
  15. Do you like sexting?
  16. Would you want me to send you nudes?
  17. Have you ever clicked pictures of yourself, naked?
  18. What’s your dirtiest fantasy?
  19. If I answer the door without any clothes on, what would you do next?
  20. Do you watch Porn?
  21. Passionate in the morning or rough at night?
  22. Have you ever been in a relationship that is ‘friends with benefits’?
  23. Have you ever been caught in the act?
  24. Do you like the idea of a sex tape?
  25. Do you read erotic stories or erotic fiction?
  26. Have you ever felt embarrassed during a sexual experience?
  27. Would you like to make out in a car?
  28. Do you like breakfast in bed?
  29. Do you make eye contact during sex?
  30. Have you ever had an inappropriate crush?

All the questions mentioned above were designed on the surface level. But now that you are confident about him, let’s dive deeper –

Deep Questions To Ask A Guy

Deep Questions To Ask A Guy That Will Bare His Soul to You
Deep Questions To Ask A Guy That Will Bare His Soul to You

Let’s face it: Small talk is annoying.  

Especially when you are here to meet a guy you want to date and build dreams with.

Now, after a while in the conversation, it’s a good time to shoot some deep questions that will rattle him emotionally. There’s nothing wrong with that.  

  1. When was the last time you cried your heart out?
  2. Have you ever been in true love?
  3. Who are you closest to in your family?
  4. What is your biggest fantasy of all times?
  5. What is one thing you regret doing?
  6. How do you cope up with people you don’t like?
  7. If you could rewind time, where would you take it?
  8. Why is your best friend your best friend?
  9. What’s one thing a woman has done for you that you will never be able to forget?
  10. Who would you sacrifice your life for?
  11. One thing that keeps you up at night
  12. Is physical attraction necessary in a good relationship?
  13. When can you say ‘My life is perfect’?
  14. Do you believe in Karma?
  15. How do you want to be remembered in the world?
  16. What’s the one thing about you, you would want to erase from people’s minds?
  17. Name one movie that changed your life for good?
  18. If you woke up 10 years later, what’s the first thing you will ask?
  19. Tell me one thing that you can do today but couldn’t a year ago?
  20. When did you first start earning?
  21. What did you do with your first salary?
  22. Have you ever been cheated by someone?
  23. Did you ever cheat on someone?
  24. Who’s your go-to family member for everything?
  25. What’s one event or instance in your life that made you stronger?
  26. What would you like to change in you?
  27. What makes you feel accomplished?
  28. What according to you is success?
  29. What kind of parent do you think you will be when you have children?
  30. Have you ever lost someone you couldn’t imagine your life without?

If you have exhausted all the questions written above, you will be already sea level deep. You will spend more time, talk more often, and meet more than usual.

There will be times when you will have no material to discuss. For those times here is a list of –

Random Questions To Ask A Guy To Keep The Conversation Going

Random Questions To Ask A Guy To Keep The Conversation Going
Random Questions To Ask A Guy To Keep The Conversation Going
  1. If you could do anything for a living, what would you do?
  2. Do you keep yourself updated with current affairs?
  3. What is the job you would never want to do?
  4. What do you love about the city you live in?
  5. If you could remove one inanimate object permanently, what would it be?
  6. Suppose you are invited to a TED Talk tomorrow, what would you talk about?
  7. Talent or Intelligence: What would you steal?
  8. What was the worst year of your life?
  9. Do you care about what others think about you? Good or bad?
  10. How will you define freedom?

Amidst all the questions and answers, you certainly don’t want the romance to dry up. So, here’s a list of –

Romantic Questions To Ask a Guy You Like

Romantic Questions To Keep The Love-Flame Burning
Romantic Questions To Keep The Love-Flame Burning
  1. How do you imagine your dream date to be like?
  2. What is the one thing that you love about me?
  3. Guess – what I like about you?
  4. Describe how you felt during our first kiss
  5. What’s the sweetest nickname you have ever heard?
  6. What’s the best romantic act you have heard of?
  7. Where would you want a romantic date: up in the air or deep in the sea?
  8. What is more important in a relationship: Communication or sex?
  9. Good sex or tight hug: what can help you relax?
  10. What is the song that instantly reminds you of me?
  11. What is your perfect family like?
  12. Do you like me being possessive about you?
  13. When other boys check me out, do you feel jealous?
  14. What’s the most romantic thing you have done in a while?
  15. Were you nervous before our first kiss?
  16. What is the best part of being in a romantic relationship?
  17. How often do you miss me when we are not together?
  18. What does soulmates mean to you?
  19. Do you believe in destiny or fate?
  20. What’s one thing I do daily that you love?

Romance is beautiful – it keeps you high in love.

You know what’s more beautiful?

When you complete each other’s sentences.

This is only possible when you know each other not only from the heart but also from the soul. To build such an exquisite bond requires effort.

Effort to know him. All the time. On a date. Over phone call. Over text.

Here’s a list that can help.

Questions To Ask A Guy Over Text That Will Bring You Closer

Questions To Ask A Guy Over Text That Will Bring You Closer
Questions To Ask A Guy Over Text That Will Bring You Closer
  1. What’s the funniest text you have ever received?
  2. What’s the funniest/craziest meme you have ever come across?
  3. Send me a picture of what’s running in your mind right now.
  4. What’s your favorite app on your phone?
  5. Send me the best photo you have ever clicked
  6. Have you ever sent a text to the wrong person?
  7. What was it and to whom?
  8. What’s the funniest picture someone has ever clicked of you?
  9. How different do you think is reel life and real life?
  10. What’s one thing you hate about your phone?
  11. What’s one thing you love about social media?
  12. What is your go-to social media platform?
  13. Have you drunk dialled?
  14. Can you live without your phone?
  15. What is your average screen time daily?
  16. If you had to choose between me
  17. What’s the stupidest thing someone could buy on the internet?
  18. What is on your Netflix Watch List?
  19. Which TV shows do you think should have more seasons but don’t?
  20. What’s the least used app on your phone?

You can’t understand a guy completely on the first date. Not even on the fifth date.

Infact, you will discover new aspects of him every time you meet him. It’s a never-ending process.

But at some point in life, you need to decide whether he is the one with whom you want to build a family. While there’s no guidebook that can decide it for you, these few questions are perfect to get a hint.

Follow Up Questions To Find Out If He Is The ONE

Follow Up Questions To Find Out If He Is The ONE
Follow Up Questions To Find Out If He Is The ONE
  1. What was the proudest moment of your life?
  2. What’s your best childhood memory?
  3. Do you want a family?
  4. What according to you is the perfect age to marry?
  5. What do you fear in a romantic relationship?
  6. What’s the best 24 hours of your life you have ever spent?
  7. Do you gradually start losing interest if you do your favourite activity multiple times?
  8. Would you advise anybody to fall in love?
  9. Are you anxious while starting a conversation?
  10. When was the last time you had a lot of fun?
  11. What is the one thing you can’t tolerate?
  12. What is your idea of a perfect girlfriend?
  13. What is your biggest realization in life?
  14. When can you introduce me to your family?
  15. What do you value most: Loyalty or respect?
  16. Are you crushing on someone right now?
  17. What do you think about marriage?
  18. Would you prefer a big fat celebration or an intimate affair?
  19. Are you scared of commitment?
  20. Who is your favourite real-life star couple?

Now that you have found you the ONE.

Should you take the big decision?

Before that,

Try asking these questions to know your future compatibility

Best Questions To Ask A Guy Before Marriage

Best Questions To Ask A Guy Before Marriage
Best Questions To Ask A Guy Before Marriage

Here are some great questions to ask a boy before marriage which can help you take the important decision of your life –

  1. How many children do you want?
  2. What would you do if you discovered that one of your children is homosexual?
  3. What would you do if your child doesn’t want to go to a college?
  4. Do you approve of the adoption of kids?
  5. If I and your family are on opposite sides, who would you pick?
  6. Work or family: what is more important to you?
  7. Do you think both the partners should equally participate in life?
  8. What is the role of a husband in your opinion?
  9. What is the role of a wife in your opinion?
  10. Who according to you should make the biggest decisions in the family?
  11. Rick and miserable or Poor and happy: What would you pick?
  12. How good are you with finances?
  13. Would you also consider a second job if what you earn from the first is not enough?
  14. Do you save money?
  15. Do you enjoy travelling?
  16. What is your opinion on retirement? Do you think you should save money for it?
  17. What would you do if someone says bad about me in front of you?
  18. What are your views on politics?
  19. How important is social life for you?
  20. What are the three things that are necessary to be happy in a relationship?


Some more…

Interesting Questions To Ask A Guy To Know If He Loves You Equally

Interesting Questions To Ask A Guy To Know If He Loves You Equally
Interesting Questions To Ask A Guy To Know If He Loves You Equally
  1. How would you take care of me if I was sick?
  2. Have you ever yelled at someone? Who and why?
  3. Can you control your anger?
  4. Is there anything you still haven’t got over?
  5. What is the time you feel most alone?
  6. Do you think life is fair?
  7. What is your favorite car model?
  8. Have you ever been backstabbed before?
  9. Have you ever cursed someone? Who and why?
  10. If you were allowed to choose a career path for your children, what would it be?
  11. For one day if you were the most powerful man on Earth, what would you do?
  12. What according to you is the toughest sport?
  13. Do you believe in the afterlife?
  14. If you had only one day to live, what would you do?
  15. What’s the one thing in the world that you feel sorry about?
  16. Have you ever lost a relationship because of your ego?
  17. Do you think you need to sacrifice personal goals for a happy relationship?
  18. If you can drive only one car all your life, what car would it be?
  19. If you met an alien, what would you do?
  20. Do you like giving nice big hugs or sweet kisses?
  21. What is one household activity you hate doing?
  22. What is your go-to midnight snack?
  23. If you were allowed to speak only one word today, what would it be?
  24. Where would you want to be locked up with your friends?
  25. Do you sing?
  26. Do you enjoy dancing in night clubs when no one is watching or on stage you have an audience?
  27. What is the one thing you’ve tried (food or activity) that you will never try again?
  28. What life stories will you narrate to your children when you are old?
  29. Stick or replace: what do you prefer when things are broken?
  30. Describe your life in one word.

Just because now you know what to ask, doesn’t mean it will be easy.

So, here are

6 Powerful Tips To Ask Questions To A Guy

1. Choose wisely

Choose wisely
Choose wisely

The questions you ask a guy on a date will surely be different from the questions you ask your potential business partner. Likewise, you will not ask the same questions on your fifth date that you asked him on your first.

So, pick your questions wisely. There’s no one-size-fits-all in long-term relationships.

2. Let it flow

Let it flow
Let it flow

Now that you have a set of interesting questions in mind, doesn’t mean you have to ask them all. Start simple and let the conversation flow. A few minutes in it and you will be able to determine which questions wouldn’t fit in the topic.

Remember, dates don’t come with a rule card.

3. Keep it light

Keep it light
Keep it light

Silences are definitely awkward. But there’s nothing wrong with it. On a run to curb the silence, don’t bombard him with your questions. Ask a question> breath> let him answer> follow up> allow him to ask  

Don’t forget the subtlety. You are trying to have a conversation, not an interrogation.

4. Listen


There’s a difference between hearing and listening. Simply, lending an ear to his answers while your inner self is lost is NOT listening. To listen, you need to be emotionally attuned to the other person. Pay attention to what he says and follow up with the questions to make him believe that you are REALLY listening.

The age-old maxim holds true even today “Great conversations require great listeners”.

5. Mix and match

Mix and match
Mix and match

There’s a reason why we crafted this list with different heads. A conversation with deep questions alone might exhaust your partner while a conversation with just fun questions will appear hollow.

To achieve the right balance, mix, and match. Change the mood and evoke different emotions in him.

6. Be in the moment

Be in the moment
Be in the moment

The idea is to build a strong foundation but if you are emotionally not in sync with the conversation – there’s no way in the world you will be able to do it.

So be there mentally and emotionally!

Over to you…

Remember, Authenticity is magnetic.

So, if you are your real self, you have nothing to fear.

These “questions to ask a boy” can ignite interesting conversations. But don’t be afraid to add your own personal touch to it.

Above all, don’t forget to have fun!