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.
Summary in Infographics
So, let’s first begin with
Funny Questions To Ask A Guy
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:
- What’s the most embarrassing thing you’ve ever done?
- What’s your biggest pet peeve?
- Tell me one instance that can make you laugh almost every time?
- Who’s your biggest celebrity crush of all time?
- What is the weirdest nickname people address you with?
- What would you choose: No Internet Ever or No TV ever?
- No shower in a week or no brushing for a week?
- If you could only eat one food for the rest of your life What would it be?
- Which fictional character would you like to play in real life?
- If you were a girl for a day, what would you do?
- How would you react if a guy asked for your number?
- What’s a compliment you’ve ever received that looked more like an insult?
- If you were ice cream, which flavor would you be?
- Which celebrity actor will play you if there was a movie of your life?
- What’s the funniest movie you’ve ever watched?
- What’s the weirdest trend in social media you have ever come across?
- What superpower have you always desired?
- What’s the weirdest thing on your bucket list?
- You are asked to make insects a popular food item in exchange for a million dollars, how would you do it?
- 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.
Personal Questions To Ask A Guy To Get To Know Him
- Do you make life decisions based on your heart or mind?
- Who is your role model in life?
- If you could be anywhere in the world right now, where would you be?
- If you didn’t need money or a job to survive, where would you live?
- What is your biggest weakness?
- What does friendship mean to you?
- What’s the best thing about being a male?
- What is your favorite movie you have watched 100 times over but ever get tired of it?
- Do you believe in Love wins everything?
- What is unforgivable in your eyes?
- How will you define your perfect day?
- What’s the biggest lie you have ever said?
- Are you a religious or spiritual person?
- How do you like to spend your Saturday nights?
- Do you like to play video games?
- What are the kinds of tv shows you like to watch?
- What is one physical feature you notice in girls as soon as you see her?
- If you had to listen to one song on loop, what would it be?
- Where would you want to live in, beach, city or mountains?
- You are best described as naughty or nice?
- What according to you is victory?
- What do you like and hate in yourself the most?
- What keeps you going in difficult times?
- One instance when you got trouble with the law?
- What’s the scariest thing you have done in life?
- What’s your favorite type of food to eat?
- What inspires you every time you hear of it?
- What’s one thing you would want to know more about?
- Who’s your favorite athlete or sportsperson?
- Where did you grow up?
- What’s the best and worst type of food you have ever tried?
- Do you have a phobia? What is it?
- What is the one thing you haven’t done in a long time but will love to do?
- What will you ask someone to find out the most about them?
- Would you rather choose Family or Career?
- What is your dream vacation spot?
- What is your favorite animal?
- What’s your family dinner like at Thanksgiving?
- Spender or saver – what are you?
- 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)
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.
- How was your first kiss like?
- Do you think I will make up for a good partner?
- Do you mind kissing on the first date?
- If you had to describe me in 5 words, what would it be?
- Is this date as good as you had imagined it to be?
- What do you tell a girl you are interested in?
- What is your go-to flirting move?
- What’s the best pick up line you have ever heard?
- What is one thing that instantly turns you off?
- How would you describe me to someone else?
- How do I look today?
- What according to you will look best on me?
- Will you brag about me to your friends?
- Do you think you are romantic?
- What would you do to make me relax on tough days?
- Have you ever skinny-dipped?
- If you had to describe yourself in 3 words on an online dating profile – what would it be?
- Have you been working out lately?
- How do you ask someone out?
- 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
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.
- Tell me about 3 events in your life that have contributed to what you are today?
- What is the one memory you want to remember more clearly?
- What’s the best advice you received or given?
- What is the one thing you don’t want people to know about you?
- What is the one thing in person you really look for?
- What’s the first thought in your mind when you see a homeless person?
- What’s the one thing you really want to master?
- One thing was fun to do but you will never do it again?
- Where do you see yourself in the next 5 years?
- If you were invisible for a day, what would you do?
- How will you earn someone’s respect?
- Have you ever done something nice for a stranger? Describe it.
- You are asked to leave the house with only one thing, what will you pick?
- What law would you like to change or abolish?
- What are you currently saving for?
- What’s your long-term dream in life?
- What’s your new resolution for this year? Are you being able to follow it?
- Stay-in or Go out: What do you prefer?
- Do you plan your day in advance or just go with the flow?
- 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
Here are some weird and freaky questions to ask a boy that will add a tinge in a conversation –
- Which celebrity do you think would make the horrible leader?
- Which historical figure doesn’t deserve to be in history?
- What do you think in today’s society needs improvement?
- What world problem do you think is a façade?
- What’s the most disgusting pick-up line you have ever heard?
- Is there anything you want to change about social media?
- Have you ever cheated in exams?
- What according to you is the greatest invention of all times?
- The egg or the chicken: what do you think came first?
- How do you set the flap of toilet paper – over or under?
- What’s your go-to dance move?
- How many nights have you gone without any sleep?
- What is the one thing you look stupid while doing it?
- Can you do it now?
- If you were a pizza topping for one day, what do you think you will be?
- When have you been the craziest?
- If you are passing by a stranger, what is the weirdest thing you can say to him/her?
- What is the weirdest flavor combination you enjoy?
- Have you peed in public? Where?
- 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
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.
- What is the favourite part of your body?
- What is your biggest turn on?
- Do you like dirty talk on texts?
- What is your favourite position?
- What do you wear to bed daily?
- What is the part of my body you find irresistible?
- Do you often have dirty dreams?
- Do you like girls making the first move?
- Have you ever bought lingerie for a girl?
- Have you ever been naked in public?
- What would you do if you were the only human alive on earth?
- What part of my body will you be staring at if I catch you in the act?
- What’s the best dressed for you: Lingerie or nothing at all?
- What is the one thing that is irresistible for you?
- Do you like sexting?
- Would you want me to send you nudes?
- Have you ever clicked pictures of yourself, naked?
- What’s your dirtiest fantasy?
- If I answer the door without any clothes on, what would you do next?
- Do you watch Porn?
- Passionate in the morning or rough at night?
- Have you ever been in a relationship that is ‘friends with benefits’?
- Have you ever been caught in the act?
- Do you like the idea of a sex tape?
- Do you read erotic stories or erotic fiction?
- Have you ever felt embarrassed during a sexual experience?
- Would you like to make out in a car?
- Do you like breakfast in bed?
- Do you make eye contact during sex?
- 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
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.
- When was the last time you cried your heart out?
- Have you ever been in true love?
- Who are you closest to in your family?
- What is your biggest fantasy of all times?
- What is one thing you regret doing?
- How do you cope up with people you don’t like?
- If you could rewind time, where would you take it?
- Why is your best friend your best friend?
- What’s one thing a woman has done for you that you will never be able to forget?
- Who would you sacrifice your life for?
- One thing that keeps you up at night
- Is physical attraction necessary in a good relationship?
- When can you say ‘My life is perfect’?
- Do you believe in Karma?
- How do you want to be remembered in the world?
- What’s the one thing about you, you would want to erase from people’s minds?
- Name one movie that changed your life for good?
- If you woke up 10 years later, what’s the first thing you will ask?
- Tell me one thing that you can do today but couldn’t a year ago?
- When did you first start earning?
- What did you do with your first salary?
- Have you ever been cheated by someone?
- Did you ever cheat on someone?
- Who’s your go-to family member for everything?
- What’s one event or instance in your life that made you stronger?
- What would you like to change in you?
- What makes you feel accomplished?
- What according to you is success?
- What kind of parent do you think you will be when you have children?
- 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
- If you could do anything for a living, what would you do?
- Do you keep yourself updated with current affairs?
- What is the job you would never want to do?
- What do you love about the city you live in?
- If you could remove one inanimate object permanently, what would it be?
- Suppose you are invited to a TED Talk tomorrow, what would you talk about?
- Talent or Intelligence: What would you steal?
- What was the worst year of your life?
- Do you care about what others think about you? Good or bad?
- 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
- How do you imagine your dream date to be like?
- What is the one thing that you love about me?
- Guess – what I like about you?
- Describe how you felt during our first kiss
- What’s the sweetest nickname you have ever heard?
- What’s the best romantic act you have heard of?
- Where would you want a romantic date: up in the air or deep in the sea?
- What is more important in a relationship: Communication or sex?
- Good sex or tight hug: what can help you relax?
- What is the song that instantly reminds you of me?
- What is your perfect family like?
- Do you like me being possessive about you?
- When other boys check me out, do you feel jealous?
- What’s the most romantic thing you have done in a while?
- Were you nervous before our first kiss?
- What is the best part of being in a romantic relationship?
- How often do you miss me when we are not together?
- What does soulmates mean to you?
- Do you believe in destiny or fate?
- 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
- What’s the funniest text you have ever received?
- What’s the funniest/craziest meme you have ever come across?
- Send me a picture of what’s running in your mind right now.
- What’s your favorite app on your phone?
- Send me the best photo you have ever clicked
- Have you ever sent a text to the wrong person?
- What was it and to whom?
- What’s the funniest picture someone has ever clicked of you?
- How different do you think is reel life and real life?
- What’s one thing you hate about your phone?
- What’s one thing you love about social media?
- What is your go-to social media platform?
- Have you drunk dialled?
- Can you live without your phone?
- What is your average screen time daily?
- If you had to choose between me
- What’s the stupidest thing someone could buy on the internet?
- What is on your Netflix Watch List?
- Which TV shows do you think should have more seasons but don’t?
- 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 Ask a Guy To Find Out If He Is The ONE
- What was the proudest moment of your life?
- What’s your best childhood memory?
- Do you want a family?
- What according to you is the perfect age to marry?
- What do you fear in a romantic relationship?
- What’s the best 24 hours of your life you have ever spent?
- Do you gradually start losing interest if you do your favourite activity multiple times?
- Would you advise anybody to fall in love?
- Are you anxious while starting a conversation?
- When was the last time you had a lot of fun?
- What is the one thing you can’t tolerate?
- What is your idea of a perfect girlfriend?
- What is your biggest realization in life?
- When can you introduce me to your family?
- What do you value most: Loyalty or respect?
- Are you crushing on someone right now?
- What do you think about marriage?
- Would you prefer a big fat celebration or an intimate affair?
- Are you scared of commitment?
- Who is your favourite real-life star couple?
Now that you have found you the ONE.
Should you take the big decision?
Try asking these questions to know your future compatibility
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 –
- How many children do you want?
- What would you do if you discovered that one of your children is homosexual?
- What would you do if your child doesn’t want to go to a college?
- Do you approve of the adoption of kids?
- If I and your family are on opposite sides, who would you pick?
- Work or family: what is more important to you?
- Do you think both the partners should equally participate in life?
- What is the role of a husband in your opinion?
- What is the role of a wife in your opinion?
- Who according to you should make the biggest decisions in the family?
- Rick and miserable or Poor and happy: What would you pick?
- How good are you with finances?
- Would you also consider a second job if what you earn from the first is not enough?
- Do you save money?
- Do you enjoy travelling?
- What is your opinion on retirement? Do you think you should save money for it?
- What would you do if someone says bad about me in front of you?
- What are your views on politics?
- How important is social life for you?
- What are the three things that are necessary to be happy in a relationship?
Interesting Questions To Ask A Guy To Know If He Loves You Equally
- How would you take care of me if I was sick?
- Have you ever yelled at someone? Who and why?
- Can you control your anger?
- Is there anything you still haven’t got over?
- What is the time you feel most alone?
- Do you think life is fair?
- What is your favorite car model?
- Have you ever been backstabbed before?
- Have you ever cursed someone? Who and why?
- If you were allowed to choose a career path for your children, what would it be?
- For one day if you were the most powerful man on Earth, what would you do?
- What according to you is the toughest sport?
- Do you believe in the afterlife?
- If you had only one day to live, what would you do?
- What’s the one thing in the world that you feel sorry about?
- Have you ever lost a relationship because of your ego?
- Do you think you need to sacrifice personal goals for a happy relationship?
- If you can drive only one car all your life, what car would it be?
- If you met an alien, what would you do?
- Do you like giving nice big hugs or sweet kisses?
- What is one household activity you hate doing?
- What is your go-to midnight snack?
- If you were allowed to speak only one word today, what would it be?
- Where would you want to be locked up with your friends?
- Do you sing?
- Do you enjoy dancing in night clubs when no one is watching or on stage you have an audience?
- What is the one thing you’ve tried (food or activity) that you will never try again?
- What life stories will you narrate to your children when you are old?
- Stick or replace: what do you prefer when things are broken?
- Describe your life in one word.
You know all the interesting questions there are.
But wait, that doesn’t mean you have enough…
Questions to Ask a Guy you Like
You can have a BIG list of fun questions to ask a guy yet be always confused about what to ask him when he is the same guy who makes you feel ticklish.
Most people seem to stutter when they are facing a person, they have feelings for.
But don’t worry, we got you. Here’s a list of random questions to ask your crush:
- What has been your most valuable accomplishment?
- Who has been your mentor in life?
- Do you write a journal?
- Which is your choice, paper book or electronic books?
- Do you order on amazon or prefer visiting the shop?
- Are you a Walmart person or no?
- If you could be a part of any tv show movie, which one would you choose?
- If you ever had a choice to time travel, which time period will you go to?
- What is the question you’ll ask the devil?
- If given one wish, what will you ask?
- Which fictional character will you want to marry?
- If you don’t have to worry about money, will you still work?
- Are you superstitious or not?
- Do you keep up with the news?
- Will you ever want to study more?
- How many items are left in your bucket list?
- If given a choice, will you take all the knowledge in the world or all the happiness?
- How do you like to end your long day?
- Will you be okay with accepting inheritance?
- Which is your favorite quote?
- Which story has inspired you the most?
- Do you think there is always a reason behind everything?
- Will you call me judgmental?
- What is your biggest type of fear?
- Which one of your five senses will you be okay to give up?
For all the girls still stuck on the “I want a date” phase, this was for you.
But for girls who are madly in love with their partners, here’s something for you.
Questions to ask a Guy you Love
Let’s all admit it: You can love a guy the most in the world and still struggle to keep the conversation flowing.
Like even though you are planning to get married one day, there will still be times when you have literally nothing to talk about.
In these times of crisis, here’s something for your rescue. 😉
- Have you ever thought about your life legacy?
- What would you want to write in your tombstone?
- Do you make wishes when you see a shooting star?
- Are you a loud sleeper?
- Do you get restless when you aren’t with your family?
- Will you ever be okay with being a house husband?
- Which is the one law that you hate?
- What has been the most difficult period in your life?
- When have you felt the most amount of love, which moment?
- Which one character in a girl makes her unattractive to you?
- What has been your most favorite compliment ever?
- How often do you get a temper?
- Are you an introvert or an extrovert in front of people?
- What do you hate to burden others with?
- Do you enjoy having friends staying at your place?
- What are your thoughts about a live-in relationship?
- A subject that you regret not studying in college?
- Do you have any ‘feminine’ qualities?
- What is your most prized possession at home?
- What bores you the most?
- Which is the most useless piece of knowledge you can think of?
- Which is the best age to forever live in?
- Do you want to know about zodiac signs?
- Which is your spirit animal?
- If your house is on fire, which are the five things you will grab first?
Now that you have laid the foundation of a good conversation, keep the conversation going with these.
Relationship Questions to Ask a Guy to Know More about your Love
Most guys are introverts and they fail to showcase the love they have for you in their heart.
But that doesn’t mean you can’t know. You just need to ask the right questions!
Remind him of your first date ever and ask him how he felt or maybe just ask him about his favorite part of this relationship.
Trust me the answers will make you feel loved like never before.
- What is your guilty pleasure when it comes to us?
- If you could rewrite one incident between us, what would it be?
- Have you ever seen me heartbroken and felt upset?
- What is your happiest memory of us?
- When have you felt like giving up on us but didn’t?
- Did I make a good first impression on you?
- Which is your favorite place to go with me?
- Do you think we met because of fate?
- Do you think we can ever find a song to define us?
- Which is your most silly way to show affection?
- What do you think is our relationship’s biggest weakness?
- What do you think is our biggest strength together?
- How do we balance each other?
- Have you ever been scared for me?
- How have you changed in this relationship?
- Which one bad habit of mine do you tolerate?
- Which one flaw of mine do you find adorable?
- Have you ever defended me in front of your friends?
- What is the one thing you will never change about this relationship?
- Do you think we are ‘right’ for each other?
- Do you think we both need to be more vulnerable to each other?
- What have you always been scared to ask me about? Ask me now?
- Describe our relationship in 3 words?
- Does love scare you or does not feeling love scare you more?
- What has been the most awkward moment for you, with me?
Now that you are savoring all the love and can’t get enough of it, why not set the mood with some…
Juicy Questions to Ask a Guy that Tickles him in the Gut
After knowing that your guy loves you so much, I am sure you are already high on… (Umm!)
But don’t jump on him, not yet. Instead, set the mood with some fun dirty questions that will tickle him down there.
Slow and steady wins the race… yes even in the bedroom! 😉
- Will you ever want to do it during my time of the month?
- Do you prefer boxers or briefs?
- Have you ever been to a strip club?
- Would you ever pay for sex to fulfil your fantasy?
- Have you ever been blindfolded during sex?
- Want to play strip poker?
- Will you want to take a sexy bath for me?
- Do you like pinning me against the wall?
- Have you ever done it on the dining table?
- Have you ever tried cybersex?
- What is that you don’t like to do in bed?
- Would you want to go in the ocean with me?
- Top two sounds you make during sex?
- Have you ever tried faking your cum?
- Are you a boob guy or a butt guy?
- Do you have feet fetish?
- Would you love to use your tongue down there often or not?
- If I give you x-ray glasses, what would you look at first?
- Would you do it in a movie theatre?
- Do you like me black lace bra or a transparent t-shirt?
- Will you love to have breakfast in bed with me?
- How often do you not shower alone?
- Have you named your package?
- Have your parents ever caught you in bed?
- Worst place to get a hickey in?
After a good session of you-know-what, keep the fire burning with some..
(who knows, you might just be ready for another round!) 😛
Sexual Questions to Ask a Guy to Trigger the Wire of Intimacy
A good and happy sex life is as important as romance in a relationship.
But often couples fail to confess or communicate each other’s needs or desires. That’s when these kinds of questions come to rescue.
Without making them feel vulnerable, you can just ask them all that they have been hiding from you in the fear of making you feel offended or hurt.
- What do I do best to make you feel desired?
- How often do you dream about sex?
- Do you want to cuddle with me right now?
- Do you enjoy being the bigger spoon?
- How often do you masturbate in a day?
- How many sex toys do you own?
- Would you ever kiss me in public?
- Have you ever enjoyed a lap dance?
- Would you find me sexy on a pole?
- Do you enjoy it when someone gives you a head massage?
- Which is the sexiest animal in the jungle that you want to be like?
- If you had two minutes with me to do anything, what would you do?
- Which ice cream flavor would you love in bed?
- What is your simplest fantasy?
- Do you like a quickie?
- Are you a virgin?
- What is your go-to kink?
- Will you want to do a threesome with me?
- Will you watch porn with me in bed?
- How many times in a day can you do it?
- Do you like to be spanked?
- BDSM, a straight yes or an absolute no?
- Do you want to join the mile high club with me?
- Have you had sex in the car?
- How would you make me have an orgasm right now?
Now that you have had some of your play in the bedroom, it’s time for some crazy fun.
Crazy Questions to Ask a Guy that will make you both ROFL
Sanity is SO boring. I mean, who at all stays sane 24*7!
Life will become so black-and-white if we always think of what’s there to come in the future.
So, relax and give him a dose of craziness with these stupid questions. Everyone needs it, to get through life!
- Describe your worst first date ever?
- What does one have to do to make you cry in a second?
- Will you ever hotwire a car?
- Which is the funniest white lie you have told?
- The lamest joke you can think of?
- Have you ever wanted an invisibility cloak for something?
- Hilarious name that you will give to your biographer?
- What is the insult which is a compliment actually that you can think of?
- What is the color of your underwear right now?
- Superman or Batman, who will die first?
- Which is the worst dish you have cooked?
- What has been your best kitchen fail moment?
- Have you ever slipped on a banana peel?
- Which dance move do you know that you can never do?
- Have you ever puked in a work party?
- Will you ever eat a strawberry as a pizza topping?
- Have you ever worn girls clothing?
- Will you ever eat Nutella and ketchup together?
- If you replace your arms with one piece of furniture in your house, what will it be?
- Have you ever planned a party that failed?
- Have you ever stolen something for fun?
- Which are the two animals that should never have a kid together?
- Which is the cheesiest pick up line you can use on me right now?
- What do you definitely do when you go on autopilot?
- Funniest Wi-Fi name you can come up with?
Had fun? Of Course you did! Look at you laughing.
But wait, now that you have him in the fun mood, keep him there with these…
Awkward Questions to Ask a Guy that Makes Him Tongue Tied
If you have been in a long term relationship, there must be hardly anything between you two to feel awkward about.
But if you have just started dating, these questions can reveal some weird things about him.
Don’t dare judge him for the answer to this question. It will ruin all the fun and will make him conscious.
- Which is the one food whose smell you love but hate the looks of?
- Have you ever passed out in a public place?
- Have you ever puked on your senior at a party?
- Which is the one thing that was your biggest regret but isn’t anymore?
- Have you ever had more than one nightstands?
- Have you ever compared bucket lists to make yourself feel better?
- Have you ever dozed off during sex?
- Have you ever been in a situation where you almost killed someone?
- Did you ever poop your pants due to being drunk?
- Who has caught you skipping class in college?
- Which is the most awkward situation you can imagine being naked in?
- Will you ever agree to giving birth to a child (if technology advances)
- Why haven’t you donated your sperm yet?
- Have you ever peed in your bed in your adulthood?
- Have you ever thought about murdering someone?
- Do you think religion is important?
- What is your birth control preference?
- How frequently do you enjoy pornography?
- What is lacking in our relationship?
- Do you think overdosing on drugs is cool?
- Do you think voting for nobody is sensible?
- Have you ever wondered how amazing the life of a dictator is?
- Would you ever be stuck in a maze forever or be stuck in the sky forever?
- Do you think you were ever in a toxic family environment?
- Do you think a temple or church should pay taxes?
Oh, wait. We also have a few…
Embarrassing Questions to Ask a Guy to Puzzle Him
I personally have a fetish: I like to see my guy’s embarrassed face! (sorry to admit that! :P)
But I am sure, there must be a few like me.
If you are one of them, just start asking these questions and trust me mid-way through it, you will be on the floor holding your stomach!
- Are you a renowned bathroom singer?
- Have you ever had a beer belly?
- Guess how many guys have I slept with?
- Have you ever called a girl with someone else’s name?
- Have you ever been in debt?
- Have you ever been arrested?
- Have you ever found someone who is ten years younger than you attractive?
- How were you dumped the last time?
- Which is the worst way you’ve dumped someone purposely?
- Have you ever got yourself tested for STDs?
- Have you ever ranked your exes based on their kisses?
- Have you ever found a friend of mine hot?
- Will you ever ditch your friends for a girl?
- Which world record you know you can never break?
- Have you ever drunk and driven? Just for the thrill?
- Do you secretly enjoy it when multiple girls hit on you?
- Have you ever sent a naughty message to someone and regretted it?
- Are you comfortable with your partner cheating on you multiple times?
- Have you ever dreamt about kissing a guy?
- Weirdest addiction you have ever had?
- Most unique fetish that you have?
- Have you ever been caught in bed?
- Will you ever choose to walk on the road naked or to give up kissing?
- Do you call people fat or healthy?
- What is the biggest romantic fail you have organised for your girl?
Ah, that’s not it.
Here are some…
Freaky Questions to Ask a Guy that will Make Him feel Uneasy
Unconventional questions have their own fun.
The weird faces, the excuses to dodge the question and also the funny answers – everything makes up for the uneasiness.
You will not understand until you try them – trust me!
- Which is the one city in the world that you never want to visit?
- What is your most unique phobia?
- Have you ever given a nickname to yourself?
- Have you ever sneaked out of your window to meet your ex?
- What is the strangest thing you have ever eaten?
- Are you a crunchy cereal or a soggy cereal person?
- If you found $1000 on the ground outside your door, what will you do?
- Which is the creepiest tattoo idea you can come up with?
- If you had a chance to invent a new word, what would it be?
- Do you enjoy listening to paranormal stories?
- Has anyone ever compared your looks to someone’s face?
- What do you do when someone body shames you?
- How awesome do you think your name is? Will you ever change it?
- Are you a cherry on the cake or ice in the drink kind of person?
- Can you choose the best amongst all Mughal emperors and mention why?
- Do you intentionally keep a check on your exes
- Have you ever said ‘Thank you’ to an ‘I love you?’
- Would you ever agree to relive a year of your life again?
- When do you think possessiveness becomes obsession?
- What is your weirdest kink?
- Will you choose to know the day of your death or the cause?
- Have you ever found a serial killer cool?
- In a state of life and death, will you agree to eat another human?
- Do you want a zombie apocalypse to happen?
- What do you do when you fall off the bed while sleeping?
After all, said and done.
Why not ask some… (and leave him hanging!)
Hot Questions to Ask a Guy to Light the Fire
The tease is fun… like SUPER fun!
For times, when you are not in mood for sex but just some dirty fun… start with these hot questions and a sexy game.
It will make him craving for you and you may just be able to get everything that you otherwise couldn’t… in return for something that he wants!
(ofcourse, you know what that is! 😉)
- Do you like the lights to be on or off?
- Describe your last dirty dream to me?
- Would you ever want to do it in the bushes?
- Do you take the lead or do you like me to take control?
- Choose the three people you would want to do a foursome with?
- Which one place do you love me to touch you?
- Which is your favourite colour on a bra?
- Can you unhook a bra with one hand?
- When did you have a one-night stand for the last time?
- Do you lick your lips when a woman is in wet clothes?
- Do you like to talk during intercourse?
- Do you like it if someone watches you masturbate?
- Do you like to be on top, or the bottom?
- Which is your favourite scenario while sexting?
- Which is your riskiest fantasy?
- Do you like to be seduced?
- Which is your favorite setup to play the game of seduction in?
- Have you ever had an orgy?
- Which is the strangest yet satisfying position you have been in?
- Do you prefer having a friend with benefits?
- Do you enjoy using food items in foreplay?
- Do you like whipped cream on me?
- Have you ever received a hand job while driving?
- Have you ever made a sex tape secretly?
- Will you do a striptease for me?
Okay, now while you both are on bed savoring each other, it’s your turn to make him feel loved with some…
Cute questions to ask a guy that will Make him Feel Loved
Something as basic as “How can you look so cute all the time?” can make him feel good and remind him of how much you love him.
There’s not much you have to do to make him feel like he is the center of your Earth… just ask a few cute questions dipped in your love and commitment to this relationship.
…and the smile on his face will be to die for!
- How do you have such amazing taste in music?
- Has anyone ever complimented you for that adorable smile?
- How do you plan an ideal date?
- What quality about you will make this relationship work?
- Do you think you have experienced love at first sight?
- Do you think your dashing looks were a deal-breaker for me?
- Do you smile whenever you see my name in your phone notifications?
- Do you know that I feel like calling you all the time but resist the urge?
- Do you ever wonder who you’ll grow old with?
- Do you ever wonder if you make me nervous?
- What will be your go-to strategy to raise your kid?
- Will you like it if I dedicate a romantic song lyric to you?
- Do you like it when I check in on you during the day?
- Will you ever give up on us? Because I don’t want to.
- How often do girls send you the heart emoji?
- What kind of music defines your personality?
- Would you mind if I brag about you to my friends?
- What would you do if my best friend hits on you?
- Have you ever tried modelling?
- Will you ever agree to travel to space with me?
- What makes you feel alive and happy?
- Are you a soft-hearted person in life?
- Do you enjoy giving away free hugs?
- Would you laugh if I say you are both cute and hot?
- Do you think you are good at cuddling?
After this, if you both are planning to go on a date the day after, we have also got you covered there! 😉
Questions to Ask a Guy on a Date
Date questions are different. Different from the questions to text or ask when you talk over the phone.
While the first-date jitters are a whole new ballgame, the butterflies don’t really sleep on the follow-up dates as well.
So, to help you calm down here’s your pre-pared list of questions to ask on a date.
- Which is your favorite movie that you have only watched once?
- Have you ever rejected a dream job opportunity?
- Which is your most favorite family tradition?
- Are you a call on the phone or a facetime person?
- Which is your favorite book to read?
- Which is the one tv show that can always make you laugh?
- Are you a fiction or a non-fiction person?
- What are the things that you are passionate about?
- Which is the one city in the world that you want to visit?
- Who has been the one person having the biggest influence in your life?
- How are you liking this date so far?
- How many dates have you been on (at the maximum) with a single person?
- Are you looking for anything serious right now or just some fun?
- What is your most favorite life adventure?
- Are you an early morning riser or a night owl sleeper?
- Which artist do you never get tired of listening to?
- Do you enjoy binge-watching or prefer taking it slow?
- Have you ever had a pet?
- Which animal do you think is the most ruthless?
- Which is the most adorable furniture piece at your house?
- Are you a team player or a lone wolf?
- How do you define a relaxing day for yourself?
- Which thing in your life are you most thankful for?
- What are the 3 random trivia facts you can instantly come up with?
- Which is your most lovable smell?
Just because now, you know what to ask, doesn’t mean it will be easy.
So, here are
(so that your conversation flows easily!)
Tips for “Conversation Starters with A Guy”
1. 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
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
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.
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
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
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!
Surabhi has a deep passion for words. She puts her heart and mind into whatever she pursues and craves for creative ventures. She has always been keen on creating original content that can make a difference. In her experience as a content writer, she has had the opportunity to work on several fields with Psychology being her favorite. Surabhi says, words have the power to transform the world, better than a sword. So she hopes to contribute her bit to this revolution. At ThePleasantConversation, she feels lucky to have the opportunity to share content capable of bringing about a change in the lives of the readers.