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200+ Good Questions To Ask a Guy – The Ultimate List


(Last Updated On: March 12, 2020)
Questions are roadways to deeper insight and knowledge. We learn better by asking questions. By asking meaningful questions, we learn about ourselves and the world which further helps us in making informed decisions in the future. The person who asks questions bids farewell to her ignorance and assumptions and puts in an effort to know something or someone.
The process of knowing your lover is endless! Your lover is changing on a daily basis and it’s important to keep knowledge of them up to date. Be it a first date or thirty-sixth date, a good question can lead to beautiful conversation and enriches intimacy between two people.

Questions to ask a guy

Questions to ask a guy

  • Would you choose to vagabond around the world or settling and growing in one place?

 

  • What characteristics of yours pushes people away?

 

  • If you had to sacrifice two out of the five senses in order to stay alive, which ones would it be?

 

  • If you had to rename our planet, what name would you give it?

 

  • What’s the most unhygienic thing you’ve ever done?

 

  • How far back can you trace your family tree?

 

  • If you were given the power to resurrect anyone famous personality of your choosing, who would you choose?

 

  • Have you ever cross-dressed?

 

  • Would you prefer to be burned alive or eaten by a cheetah?

 

  • Are you contemplative or action-oriented?

 

  • Do you grow in the solitude of the company?

 

  • Are you a slow learner or a fast learner?

 

  • Which antagonist of a movie or a book, do you relate to?

 

  • Tell me the weirdest food combination you’ve tried so far or would like to try?

 

  • Do you take time for granted?

 

  • Do you believe in the superiority of Homo Sapiens over other creatures on our planet?

 

  • Is there any social cause you feel strongly about?

 

  • Are you in terms of your mortality?

 

  • Do you read a newspaper every day?

 

  • How much have you explored yourself sexually?

 

  • Do you feel the weight of societal expectations?

 

  • Has your masculinity ever suffocated you?

 

  • How many lovers have you had till now?

 

  • Do you want your partner to be your exact opposite or your carbon-copy?

 

  • Do people change or do they intensely become themselves?

 

  • Which household chore you enjoy the most?

 

  • How do you feel about the 21st century?

 

  • What’s the most rebellious thing you’ve done?

 

  • Which aspect of your childhood do you miss the most?

 

  • Are you running from yourself?

 

  • Can you recall the kindest thing someone ever did for you?

 

  • What’s the funniest thing that has happened to you recently?

 

  • Are you in touch with your ethnicity?

 

  • Which disease are you most afraid of acquiring?

 

  • Are you spiritually awakened?

 

  • Have you ever lost someone to death?

 

  • Choose between stargazing and cloud gazing.

 

  • Did you enjoy group projects as a student?

 

  • Any academic or extracurricular achievements that you are proud of?

 

  • Any movie/book that you are embarrassed to admit that you like?

 

  • What’s your favorite nursery rhyme?

 

  • What’s the most shocking custom from your culture?

 

  • What’s the most illegal thing you have ever done?

 

  • Which mobile application suits your personality?

 

  • Do you trash talk about others?

 

  • What conspiracy theories do you believe in?

 

  • How do you see yourself as? What’s your self-image?

 

  • What’s the most erotic experience that you’ve had?

 

  • Do you prefer the carefreeness of childhood or wisdom of old age?

 

  • Are you open to the idea of religious conversion?

 

  • What type of fragrances do you like?

 

  • Would you call yourself a family guy?

 

  • Are you quick in stepping out of your comfort zone?

 

  • Would you assume the responsibility of a godparent?

 

  • Do you think consumerist purchases brings one happiness?

 

  • Do you have a self-care routine?

 

  • Do you think life is a tragedy or a comedy?

 

 

  • What’s your comfort food?

 

  • What are your thoughts on polyamory?

 

  • Do you believe in love at first sight or is it overly romanticized for you?

 

  • Have you tried any adventure sports?

 

  • What was the last time you did anything for the first time?

 

  • Do you have a dream house in mind?

 

  • Do you think social media addiction gets better of you?

 

  • What expensive hobby would you like to invest your money and time in?

 

  • Have you ever farted in public?

 

  • Do you think you would be a better parent than your own parents?

 

  • How do you imagine your life to be in the next ten years?

 

  • What life skills are you ashamed of not learning?

 

  • Which was the hardest year in your life?

 

  • Was there anyone who changed the way you think?

 

  • What’s the most violent thing that you’ve done?

 

  • Would you prefer to love or be loved?

 

  • What is your source of inspiration?

 

  • What is the meaning of your name?

 

  • Are you melancholic or joyful by nature?

 

  • Do you forgive easily?

 

  • What’s your favorite proverb?

 

  • What’s the bitterest lesson you’ve learned so far?

 

  • What do you think about before falling asleep?

 

  • Have you learned any musical instruments?

 

  • At what age did you become serious about your life?

 

  • Any hidden behavior you had carried out till now?

 

  • What will be your reaction if your nightmares were to true?

 

  • How often do you lie to your parents?

 

  • If today was the last day of your life, how would you live this day?

 

  • Till what age do you want to live?

 

  • Has there been a day where there was not a single penny in your pocket?

 

  • Do you know how to crack a joke?

 

  • How many dating apps have you installed?

 

  • Confess one mistake of yours which is not known by anybody.

 

  • What kind of behavior attracts you the most?

 

  • If you were to acquire supernatural powers, what would you change?

 

  • How much time do you spend on PUBg?

 

  • Is there any habit that you want to change but have unable to?

 

  • Did you have a crush on a teacher in your school days?

 

  • What do you think about women?

 

  • What do you think about women who are in the job profession?

 

  • Do you know how to cook?

 

Flirty questions to ask a guy

Flirty questions to ask a guy

Some people are pro at flirting while others depend on the internet. Here are some questions you can ask to flirt with a guy or give a hint that you’re interested in him.

 

  • What do you prefer spooning or cuddling?

 

  • When you think about me, do you feel butterflies? 

 

  • Describe your idea of foreplay?

 

  • If you had to describe yourself as a boyfriend in 3 words, what would they be?

 

  • Would you let me give you a massage?

 

  • Are you good at text flirting or face to face flirting?

 

  • If you could swap your one facial feature with me what would it be?

 

  • Have you ever experienced love at first sight? I have when I first saw you.

 

  • Do you get hiccups often? Because I’m thinking about you 24/7.

 

  • If I wanted to hold your hand while getting an injection, would you let me?

 

  • If you get 3 wishes, and your wishes could be only fulfilled if it includes me. What would you wish for?

 

  • If I followed you home, would you keep me?

 

  • Are you sure Leonardo da Vinci is not your dad? (Why) because you sure a great piece of art.

 

  • What do you prefer, a quick shower or a bubble bath?

 

  • You definitely seem like a guy who has a type, What’s your type? Am I your type?

 

  • Do you like the tv show F.R.I.E.N.D.S? (Yes) then ask How you doin*

 

  • Thoughts on a prenup? (Followed by I really don’t mind signing one with you)

 

Questions to ask a guy over text

Questions to ask a guy over text

We all have been at a stage where we are scared to talk to guys, yet alone be on a date. And some are introverts, who prefer texting more rather than meeting in person. But this can also be tricky. How do you keep the conversation going? How to get know him better without actually seeing him? 

 

Here is your answer. Ask a guy these questions over texts and even on a date.

 

  • If you had to start our conversation with one pick up line, which would it be?

 

  • Which place is more affordable, Bali or Indonesia?

 

  • What’s your favorite kind of shoes?

 

  • If you have to make up a past Story Every time you meet someone, what would it be?

 

  • If you could be one character from a book you’ve read, which would you be and why?

 

  • Tell me one lie and one truth and I’ll figure which is truth.

 

  • Can I trust you with all my secrets?

 

  • If I ask you out on a date, where would you want me to take you?

 

  • Hoes before bros or bros before hoes

 

  • When we first talked, how did you imagined I looked like?

 

  • If you can give one compliment to everybody, every day, what would it be?

 

  • If you had to be a sloth or a koala bear, what would you be?

 

  • Which is your most likable ocean?

 

  • If you could throw one thing in the Bermuda triangle, what would you throw?

 

  • What’s the most recent picture in your gallery. Can you send it?

 

  • Have you ever considered that your life could just be a movie with some random director and okayish storyline?

 

  • If you and I get a pet together, what would you want to name it?

 

Personal questions to ask a guy

Personal questions to ask a guy

Everybody takes their own time to open up be it a girl or a boy, but asking the right questions might speed up the process. From family to Friends to secret, you’ll get to know everything just by asking the right questions in the right way. To ask a guy about his personal life can be a bit difficult but not impossible.

 

Following are some questions you can ask a guy about his personal as well as professional life.

 

  • If you were about dying,who would you spend your last moments with, your family or your friends?

 

  • If you could live 2 life simultaneously, whose life would you choose to live?

 

  • In three words, describe your worst Habit.

 

  • How often do you curse?

 

  • How many siblings do you think you should have?

 

  • In an alternate reality, what would you be?

 

  • Would you rather have a rich Future with a dark past or have a dark future with a dark past.

 

  • Do you have a specific selfie angle?

 

  • What song would you choose to dance on your wedding day?

 

  • Tell me a weird yet a sad story

 

  • What are you good at horse racing or car racing?

 

  • If you could be in one Quentin Tarantino movie and one Christopher Nolan movie which would it be and why?

 

  • What would the inscription of your tombstone be?

 

  • If you get to choose where you get buried, which place would you choose?

 

  • Do you believe in the afterlife?

 

  • What was the saddest time of your life?

 

  • If you could go back in the past, what event of your life would you like to change?

Dirty questions to ask a guy

Dirty questions to ask a guy

Once we are comfortable with someone, we are completely our true selves. We talk about the most random to the most dirtiest thing and we don’t hesitate because we trust the person and you’re in your comfort zone. 

 

If you’re looking for some questions to start an *ahem* 😉 that conversation, I have the perfect list for you.

 

  • Have you ever considered skinny dipping in public?

 

  • If you get kissed on a body part which would it be?

 

  • Do you prefer to sleep naked or in boxers?

 

  • Describe your perfect fantasy?

 

  • How long do you think you last in bed?

 

  • What does a girl have to do to turn you on?

 

  • If you could send me pictures of your body except your face, what would you send?

 

  • Do you prefer to role-play?

 

  • Lap dance or strip dance?

 

  • Are you a cigarette after sex kind of guy?

 

  •  Thoughts on one nightstand

 

  • Is it okay for guys to moan out loud?

 

  • What place do you love to get touched?

 

  • Do you have a name for your crotch?

 

  • Which celeb do you often fantasize about?

 

  • What place do you prefer the beach or a public restroom?

 

  • If you could do one fantasy which would it be?

 

Questions to ask a guy to know him deeper

Questions to ask a guy to know him deeper

There are 2 types of guys, the sensitive ones and the tough ones. Get to know a guy more and more, you need to be in his zone and he needs to have trust in you.

Here’s a list, you can try to ask to get your guy to trust you and tell you the tiniest secret of his life.

 

  • Describe your idea of a perfect relationship.

 

  • If you could tell one thing to your parents that you were always afraid to say what would it be?

 

  • If you could take on fear which would it be?

 

  • Which animal are you allergic too?

 

  • What is the tiniest detail about yourself?

 

  • How do you think other people see you?

 

  • Would you ever like to change anything about yourself?

 

  • What was the happiest point of your life?

 

  • What is your thinking about forever?

 

  • Do you hold grudges or you forgive easily?

 

  • Do you think it’s necessary to lie if you’re trying to save a friendship or a relationship?

 

  • How many times are you willing to forgive a person before completely cutting them off?

 

  • As a child, what monster did you though was under your bed?

 

  • Would you say that you had a good childhood?

 

  • What’s one incident from your childhood that still haunts you?

 

  • Do you consider yourself a feminist?

 

  • What according to you, is a perfect and ideal life?

 

Funny questions to ask a guy

Funny questions to ask a guy

What’s better than seeing your favorite person laugh and knowing you’re the reason. And you might wonder how to achieve that. Well the answer is simple well the questions are 

Read below to find some hilarious questions you can ask to have a great laugh.

 

  • Have you tried sticking your fingers in your nose and eating the mucus?

 

  • What’s the thing that you still laugh about?

 

  • Tell me a funny childhood story?

 

  • Would you rather sleep with dog poop or cat poop

 

  • If you could be allergic to one animal which would it be?

 

  • Would you rather be Kermit the frog or baby Yoda

 

  • If you had to change your current job with being a male stripper or a gynecologist what would you choose?

 

  • If there was a race between a cheetah and a horse, which animal would you bet on?

 

  • Name any three makeup brands

 

  • If you had to choose the most boring activity to survive, which activity would you choose?

 

  •  In what ways can you make a date funny?

 

  • If you had a chance to feature in Playboy, how would you like your picture to be

 

 

  • Have you tried dressing up as a clown and scare kids?

 

  • If you could set up life on another planet which would it be?

 

  • Tell me a funny conspiracy that you think is true?

 

  • If you could be one celeb’s child who would it be?

 

  • Will, you ever pee in a public place?

 

Honest questions to ask a guy

Honest questions to ask a guy

At a point, we all need someone who is honest with us. Start off by asking questions…

 

  • Do you believe in karma and afterlife?

 

  • Would you be an economist or an ethic professor?

 

  • What do you think about the women’s march?

 

  • If you could be one female influencer which would you be?

 

  • What is the most embarrassing story of your college life?

 

  • How often do you lie?

 

  • Do you have any role models?

 

  • Describe your perfect alcoholic drink

 

  • How many books have you read so far?

 

  • Bringing books home or reading in a library

 

  • Which is better, movies or books?

 

  • Go for hiking or go to nature’s theme park

 

  • How many ex’s you had and describe them in two words?

 

  • If you had to replace your legs with one of the animals which would it be?

 

  • Name the coolest nickname you had

 

  • How do you feel about getting old?

 

  • If you could be the president of the country, what would be your first decision?

 

Questions to ask a guy on a date

Questions to ask a guy on a date

  • What do you look for in a person? 

 

  • Does the past really matter to you?

 

  • What do you notice First on your date?

 

  • Do you think dating apps really work?

 

  • Are you bothered by your date’s family background?

 

  • Do you believe that people can really change?

 

  • Can people still be friends even after breaking up?

 

  • What do you think lasts long, love marriage or arrange marriage?

 

  • How much are you willing to spend on the first date?

 

  • How do you feel about breaking the dating stereotype?

 

  • Have you seen something very unusual during your past relationships?

 

  • Which one of your past relationships did actually helped you grow?

 

  • Does dating women of different cultures help one to widen their perspective on women’s?

 

  • Tell me some of your weird first date stories?

 

  • What is the fanciest place you’ve been on your first date?

 

  • Movie date or picnic?

 

  • Do you think meeting your girlfriend’s family after a few dates are really helpful?

 

Random questions to ask a guy

Random questions to ask a guy

Start off a conversation with random questions and break the ice- that is the motto that a lot of people believe in. And don’t have any weird questions, fear not. I’ve got you covered.

 

  • What do you think is the best way to break the ice between two people?

 

  • When was the last time you played a prank in public? What was the prank

 

  • Have you scared someone so much that they shit their pants?

 

  • Have you ever peed in a pool?

 

  • Would you rather stay in a fancy hotel with no money or stay in a cheap motel with a thousand dollars?

 

  • Would you rather pee nonstop for a week or not being able to poop for a week?

 

  • If you could be a baby’s soft toy which toy would be?

 

  • Would you rather run at a park or run in the street like children?

 

  • If you could fight in world war 2, which county would you choose to fight for?

 

  • Imagine its the end of the world, and it’s 11 hours before humanity is wiped off, what would you do?

 

  • Would you rather sleep naked with tons of people watching you or walk naked with few people watching you?

 

  • Describe an imaginary date that you think you want?

 

  • Tell me your one version of a tongue twister?

 

  • Do you have your own Netflix account or you use someone else’s?

 

  • Name 3 extinct species of animals and which out of those 3 would you choose as a pet?

 

  • If you could be a celebrity’s assistant, who would it be?

 

  • Would you be a bad doctor in a very respectful hospital or a good doctor at a very bad hospital?

 

Deep questions to ask a guy

Deep questions to ask a guy

As if a random question is not enough, here are some more questions to get your guy into the feels and start to know him better

 

  • Have you ever dated a girl who is attracted to someone else?

 

  • What’s your idea of an afterlife?

 

  • Do you believe in vampires and werewolves?

 

  • If it was in your hands to choose how you die, how would you?

 

  • Do you have different personalities for different people?

 

  • What is the best and worst creation of god?

 

  • Can our minds tell the difference between reality and illusion?

 

  • Do you think Illuminati is real?

 

  • Are we under an obligation to make sense to everyone?

 

  • What is your purpose in life?

 

  • Do you think murder with no cause is justified?

 

  • Do you think you’re an emotional guy and do you let your emotions get the best of you?

 

  • Do you think everyone has the right to be happy or that they should earn their happiness?a
  • What is one thing that always gets your thinking about life?

 

  • Do we all deserve to live even after all the bad things we’ve done?

 

  • What’s the lowest point in someone’s life?

 

  • Do you think action done under certain situations can make or break a person?

 

  • Do you think the random wave of sadness we get is due to our past life or it is a kind of signal?

 

  • Do women deserve an equal position as the man or do they just belong in the house?

 

  • Would you date someone who is earning more than you or is somewhat more successful than you?

 

Weird/odd question to ask a guy

Weird/odd question to ask a guy

Here we are at the last segment of the article as if everything else does not crack open a guy this could or could not, as every guy is different from the other. Maybe you’re trying to know him, flirt with him or just trying to have a laugh, it all comes to how you ask or how to get him to talk 

 

  • Do you want to be a pirate?

 

  • What is the one scene that always makes you laugh?

 

  • What do you desire more, health or wealth?

 

  • Would you rather be a disgusting person with good looks or a good person with disgusting looks?

 

  • Have you thought about how Doctors perform brain surgery?

 

  • Are you competitive when it comes to board games? Which board game you love the most.

 

  • What do you think about the saying, looks can be deceiving?

 

  • What would you do if you wake up and its 10 years in the future, but you have no memory of anything.

 

  • What is the most important thing you know and who taught you that?

 

  • Have you ever saw a disturbing scene with your parents or younger siblings?

 

  • Tell me a weird hospital story

 

  • Have you ever said I love you after talking to your boss?

 

  • What is a weird thing that you did too your friends?

 

  • Would you rather lick hen’s poop and survive or just die?

 

  • Are you the dumper or the dumpee (dumper: the one who ends the relationship. Dumpee: the one who gets dump)

 

  • Have you ever been to an orgy party?

 

  • Have you ever had a wet dream about an old woman?

 

There you have it, everyone. Some really weird, funny, deep and disturbing questions to ask a guy and to make space for communication in your relationship. Now you can know his fear, his embarrassing moments and everything about it and make way for your own conversation.

 

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