Five years ago, I noticed a guy at my friend’s birthday party. He was damn cute and sexy.
I was quite introvert back then, shy to start a conversation with anyone. So, I was sitting in corner checking my phone.
But, suddenly someone tapped me on the shoulder- I turned around. I couldn’t believe my eyes. God, that was him!
He asked, ‘Hey, would you like to have a drink with me?’
Out of full excitement, I blurted out, Yes!
He asked, ‘which one’?
I answered, red wine. He said he also liked red wine. That was it! He just wanted to know my taste.
In the beginning, it was really difficult and awkward as I had no idea how to start a conversation with him.
The very moment I realized the importance of good communication skills and questions. It’s indeed important to know icebreaker questions to start conversation with a guy who interests you.
You may not know what to say when you’re meeting someone for the first time. It’s completely natural as it happens to many people.
Asking good questions about each other is part of good communication. Also, when you ask the right questions, you’ll easily find out whether he’s the right guy for you or not.
I’ve listed some cool and interesting questions to ask a guy to break down all silences. I assure you that these questions will definitely bring you closer and help to discover things about each other.
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List of Questions To Ask A Guy
Make sure you use these questions to initiate a conversation. Yes, in the beginning, you’ll be curious and excited, but don’t ask too many questions. It might end up like an interview.
It’s important to ask good, cute, and some interesting questions to know the guy you are interested in.
Following are some of the causal questions that will help you know the guy’s likes and dislikes and personality.
Good Questions To Ask A Guy
- What’s your dream job?
- Do you like your current job? What do you enjoy the most/ least about your current job and why?
- Do you like to get a job or start a business?
- What was your worst job and why?
- Where do you see yourself in ten years from now?
- Who is your favorite singer or artist?
- Can you tell me about your childhood? What is your fondest childhood memory?
- How is your relationship with your parents?
- Do you live with your parents?
- How many siblings do you have?
- Do you have any favorite cartoon character? What was your favorite childhood cartoon show?
- Which is your favorite car?
- Which is your favorite sports team and why?
- What are you most scared of and why?
- Who is your biggest idol?
- If you win a million dollars lottery, how would you spend it?
- Do you believe in astrology, why /why not?
- If your life was a movie, what would the title be?
- Do you believe in the existence of aliens?
- What is better for you: to take shower in the morning or at night?
- What is the most uncomfortable outfit you’ve ever worn?
- What do you like most about your hometown?
- If you have to change your name, what name would you choose?
- What is your favorite app on your mobile and why?
- Can you survive alone in the wilderness for a month?
- What is your regular bedtime routine?
- What one behavior, according to you, makes someone creepy?
- What’s your worst luck ever? Have you ever heard any bad luck stories?
- What’s your favorite sound to hear?
- Do you like cooking? Have you ever learned how to cook?
- What is the best thing about being a guy?
- What makes you feel stressed and how do you handle it?
- Have you ever met or seen any famous person? Who?
- If you could be an expert in one area, what would it be?
- Who is your favorite author?
- What is the most unusual thing you’ve ever done?
- What food do you hate the most and why?
- Have you ever walked out of a movie theatre? If so, which one and why?
- Who is your favorite villain in cinema?
- Do you like horror movies?
- What is your favorite recreational activity?
- What’re the most useful skills do you have?
- How often do you clean your room?
- What’s your favorite month of the year?
- What are your hobbies?
- How many of you’re there in your family?
- What do you like to do in your free time?
- How do you cheer up yourself?
- Do you have a pet?
- What’s your favorite holiday memory and why was it so memorable?
- What’s your favorite season?
- Do you like hunting?
- What is the most expensive thing you have bought for someone else?
- Have you ever been jealous of your brother or sister?
- Have you ever been jealous of your closest friend?
- Were you popular in school days? How?
- What is the most adventurous thing you’ve ever done?
Cute Questions To Ask A Guy
- What makes you smile instantly?
- If you could listen to one song for the rest of your life, which would you choose and why?
- What are the things you do or say to cheer up your partner?
- Do you like to cuddle?
- Who is your first crush?
- How often do you like to hang out with your girlfriend?
- Have you ever cried while watching a movie at the cinema?
- What do you enjoy doing the most with your family?
- What is your favorite vacation spot and why? Which is your favorite place to travel, why?
- What is your favorite movie genre and why?
- When you meet a girl for the first time, what do you notice at first?
- What are your hobbies?
- What’re your favorite sports to watch? Why?
- If we were dating, how would you like to celebrate our first anniversary?
- What’s your favorite food? Why do you like it so much?
- What’s your favorite restaurant and why?
- What is your favorite romantic activity?
- What was the most frightening moment of your life?
- What do you like to do on a rainy day?
- What’s your favorite video game?
- What’s your favorite time of the year?
- Which place is on your bucket list?
- Do you like going to concerts? Which is your favorite band?
- What’s the simplest task that makes you nervous?
- Do you like dancing? What kind of dance do you like?
- Who is your celebrity crush?
- Do you like reading novels? Which is your favorite?
- Are you an introvert or an extrovert?
- What qualities do you expect from your girlfriend?
- What would you like to do on your first date?
- Do you appreciate when a girl makes the first move?
- What compliments do you get most often?
- What would you like to be: my friend or more than a friend in the future?
- Why are you single?
- Can you tell me how you want to kiss?
- Can you help me to get over my ex?
- Did you notice that I like you?
- What is your secret fantasy?
- Do you like my friends?
- Which superpower would you like to have and why?
- Have you ever won first prize in the dream?
- Which word comes first in your mind when someone asks to describe me?
- Which one word comes first to your mind when someone asks you to describe yourself?
- What would be your three wishes if a genie came out a bottle?
- Would you want to tattoo your skin for me?
- If you could invite anyone for dinner, who would it be and why?
- What do you think about live-in-relationship?
- Do you have any nickname? Do you feel happy when someone calls you by your nickname?
- Would you introduce me to your parents?
- What would you do, if I am scared and alone at home?
- What is the freakiest thing about me that you love?
- If in future we live together, who will be paying the bills?
- How would you help me to keep our apartment clean?
- Does it make you feel good when I appreciate your looks?
- If I have to make your dinner, what do you want it to be?
Funny Questions To Ask A Guy
- What is your favorite comedy?
- Do you snore while sleeping?
- What is your hidden talent?
- What’re the funniest things you’ve ever done or seen in public?
- If you could be any animal what would you be and why?
- What is the dumbest thing you’ve ever done to get a crush’s attention?
- Do you sing in the shower?
- Do you watch women TV series?
- Have you ever fantasized about your best friend’s girlfriend?
- Are you afraid of ghosts? Have you ever experienced paranormal activity?
- Do you believe in vampires? Is there any proof that they exist?
- Have you ever stolen anything from anyone and no one knows about it?
- Which animal would you like to be and why?
- If you could be invisible for a day, where would you go and what would you do?
- What fictional character you would like to be and why?
- Have you ever made a prank call?
- Have you ever been kicked by an animal?
- Have you ever fallen down the stairs?
- What’s your funniest online dating experience?
- What’s the craziest thing you’ve seen online recently?
- What would you do if you lost your swimsuits while swimming?
- If you could slap anyone in the world who would you choose and why?
- Do you think you’re attractive?
- Have you ever pranked anyone?
- Have you ever faked crying?
- Why do you call it lipSTICK, if you can still move your lips after using it?
- Are you naughty or nice?
- Do you dance crazy when you’re alone?
- What’s the one funny thing that you would do when no one is around?
- Have you ever tried walking in heels?
- Have you ever put on makeup?
- Do you ever talk to yourself in the mirror?
- Do you think you’re a happy person? Why?
- Do you like rollercoasters? Have you ever peed on your pants during roller coaster rides?
- Has anyone accidentally walked into your bathroom?
- What cartoon character do I look like?
- Would you kiss a girl on the first date?
- What is your favorite thing to wear in the bed?
- What was your worst vacation ever?
- What was your funniest childhood memory?
- Do you know what I’m thinking right now?
- Have you ever cheated on the exam during school?
- Do you like being tickled?
- Are you afraid of any funny/silly things?
- How would you rate me, if you had to rate me on a scale of 1 to 10?
- What are your best-hidden talents?
- Can you fake any type of accent? If yes, would you like to show me?
- Have you ever broken a bone? Why?
- Can you play poker?
- Do you know any magic tricks?
Naughty Questions To Ask A Guy
After your conversation deepens with a guy, you can take chances on some naughty questions. It lets you feel comfortable with one another, physically and mentally.
These naughty questions will surely help you to explore your relationship. You may create naughty memories together and become closer than before.
Flirty Questions To Ask A Guy
- How can you be single?
- Why are you so cute?
- Do I make you nervous?
- Do you want to go out with me?
- Have you ever dated two girls at the same time?
- Do you like to kiss in the dark or kiss in the rain?
- Do you like to cuddle?
- Would you kiss me on the forehead?
- Would you kiss me on the neck?
- Would you ever bath with me?
- Have you ever liked one of your best friend’s girlfriend?
- What kind of outfit would you like to see me in? Would you like to see me in long dresses or mini skirts?
- Would you hold my hands in public?
- Do you want me to give you a massage at your back?
- Where do you want to kiss me?
- Are you a virgin?
- What is your favorite organ of a female body?
- What is your favorite type of lingerie?
- Do you see me seductive?
- Do you want to be naughty with me?
- Do you want me to talk dirty?
- Have you ever dreamt about me?
- Have you ever been jealous seeing me talk to another guy?
- Have you ever fantasized about me?
- If you could only kiss me once, where would it be?
- How would you start with me if I was in your bed right now?
- Have you ever had a dirty phone conversation?
- Have you ever been seduced by someone?
- If I had chocolate all over my body, would you lick it off?
- Have you ever bought lingerie for a girl?
- Do you know how to unhook a girl’s bra?
- What would you do if we were together and home alone?
- Have you ever gotten a lap dance?
- Would you ever want to be blindfolded?
- Do you want to have a sexy bath with me?
- Would you like to help keep my body warm?
- Can you help me to undress?
- Do you know, you make me smile when I think of you?
- Do I make you smile?
- What excites you about me?
- Do you know what exactly a women wants?
- Is it wrong to have dirty thoughts about you?
- Have you ever gone on a blind date?
- What’s your all-time favorite foreplay?
- What’s the dirtiest thing you’ve ever done with your partner?
- If you knew magic, what piece of my clothing you would like to disappear? Why?
- Would you like to get a massage from women? If yes, which part would you like the most?
- What turns you on instantly?
- What turns you off?
- Would you want me to undress you or you would do it yourself?
- If I could do anything to you right now, what would it be?
Freaky Questions To Ask A Guy
- Have you ever been over drunk and said- whatever you wanted to say?
- Have you ever driven drunk?
- Do you like being drunk? Does it make feel good?
- If today was your last day, how would you spend it?
- What is the craziest thing that you would do for me?
- Have you ever wanted to be women?
- Have you ever cheated on your girlfriend?
- Have you ever had a one night stand?
- Have you ever seen anyone naked accidentally?
- What do you wear in bed? Do you sleep naked?
- Have you ever been caught playing with yourself?
- What’s your favorite porn?
- What’s your favorite sex position?
- Where’s your favorite spot to make out?
- Have you ever thought about making a sex tape?
- Can you send me your sexy picture?
- Do you prefer to make love keeping the lights on or off?
- Have you ever taken a shower with someone of the opposite sex?
- Have you ever sunbathed nude?
- Have you ever had sex in the back seat of a car?
- Have you ever tried skinny dipping?
- Have you ever played strip poker?
- Have you ever demanded a nude photo of your ex-girlfriend?
- Have you ever sent your naked picture to someone?
- Have you ever made love to someone who is ten years older than you?
- Have you ever hooked up with your girlfriend’s best friend?
- If you’re still a virgin, what do you want your first time to be like?
- If you could slept with any porn star, who would you choose?
- Have you ever done sex with more than one person in one day?
- Have you ever hooked up with a coworker?
- Have you ever gone to a strip club?
- Have you ever paid for sex?
- Have you ever read an erotic novel?
- Have you ever done under water?
- Do you prefer to be rough or sensual?
- If we were in the same room right now, how long would it take for you to strip me naked?
- Have you ever slept with someone, and regretted the next morning?
- What’s the freakiest sensual thing you’ve ever done?
- Have you ever felt passionate while texting on the phone?
- Do you like sexting? Have you ever tried it before?
- Do you think you’re a good kisser?
- Have you ever eaten something fall on the floor?
- Do you lick your plate?
- Have you ever been caught watching porn by your parents?
- What’s your worst sexual experience?
- Would you love to visit a nude beach?
- Do you like being tied up?
- Do you prefer women in Lingerie?
- Do you like to dominate women in bed or enjoy leading in your way?
- What’s your most disturbing thought?
Awkward Questions To Ask A Guy
- What was the most embarrassing moment of your life and how did you deal with it?
- Have you dated a woman who was much older than you?
- What do you dislike about me?
- Have you ever had a wet dream?
- Have you ever hooked up with the same gender?
- Would you marry a girl who is not a virgin?
- Do you love me?
- How did you break up with your ex-girlfriend?
- Have you ever been caught while shoplifting?
- Am I better looking than your ex-girlfriend?
- Who is better kisser me or your ex-girlfriend?
- Do I look fat in this dress?
- Which color underwear are you wearing right now?
- Have you ever suffered from sexually transmitted diseases (STDs)?
- Have you ever been addicted to any drugs?
- Have you ever kissed a guy?
- What’s one silliest thing you’re passionate about?
- Do you want me to ask sexual questions?
- How many people have you slept with so far?
- Have you ever been attracted to a guy?
- Have you ever sent a naughty message to a wrong person and got into trouble?
- Have you ever gotten involved in sexual activities for money?
- Have you ever hooked up with your teacher?
- Have you ever practiced kissing in a mirror?
- What is your worst habit?
- Have you ever had a wardrobe malfunction?
- Have you ever farted in public and blamed someone else?
- Do you drool in your sleep?
- Have you ever tasted your sweat?
- Have you ever been caught while checking someone out?
- Have you ever posted something idiotic on social media that you regret?
- Do your feet smell bad?
- When was the last time you wet the bed?
- Have you ever been rejected by someone you like?
- Would you hook up with an older woman?
- Have you ever lied about your age to impress your crush?
- Name a person you would never hook up with?
- Do you like me as a friend or something more?
- Do you talk in your sleep?
- Have you ever tasted ear wax?
- Has your ex-girlfriend ever embarrassed you in public?
- Have you ever been caught checking out a girl?
- Have you ever been slapped by a girl in public?
- Have you ever written a love letter in your school days?
- What is the hottest movie scene you’ve ever watched?
- Do you have any unusual phobias? If yes, how do you handle it?
- Are you conservative or a liberal person?
- Have you ever been in a physical fight with anyone?
- What’s the weirdest text you’ve ever received from a girl?
- Have you ever gotten dumped through text?
Personal Questions To Ask A Guy
After some good, fun, light-hearted, and naughty questions now it’s time to get to know someone on a deep level.
Some of these questions are truly powerful. Don’t rush; if it’s a guy you have a crush on and you don’t know well, you opt some random questions first. But if it’s someone you connect with deeply, then these questions can take your relationship to another level.
Are you ready to dig into deep secrets?
Personal Questions To Ask A Guy
- Do you prefer to live alone or live with your family?
- What’s the one thing you would like to change about your family?
- What’s your biggest achievement in life?
- What was the most disheartening moment of your life?
- Are you scared to die? Why or why not?
- If you had a time machine, wherein the past would you go and what would you do?
- What’s the greatest lie you’ve ever told your parents?
- Have you ever gotten good compliments from your crush?
- What’s your biggest regret in life which you’ll never forget? What is one thing you’ll never regret in your life?
- Who was your first love? Do you still love your first love?
- At what age, you dated a girl for the first time?
- Have you ever taken advantage of someone who was madly in love with you?
- Have you ever loved someone madly?
- What are the best three words you can use to describe yourself? What would the best three words would your friends use to describe you?
- What is your most treasured possession?
- In your opinion, should women stay at home or go out to work?
- Have you ever had a crush on your teacher or someone much older than you?
- Have you ever been arrested, if so, what was your crime?
- What are your personal strength and weakness?
- Do you smoke and drink? At what age did you start drinking?
- Have you ever tried drugs? How does it feel?
- What’s your dirtiest secret that you haven’t told anybody?
- What is your ideal date?
- What is the funniest or scariest dream you have ever had?
- Are you religious? Do you pray regularly?
- What was the worst date you’ve ever been on?
- Do you believe in reincarnation?
- Have you ever said “I love you” when you didn’t mean it?
- Tell me something interesting about yourself that no one else knows?
- Have you ever met someone online and then in person? What was your experience like?
- What do you think about a live-in-relationship?
- What is your view on religion?
- Are you addicted to anything?
- If a hot girl comes to your side while you are with me, what would be your reaction?
- What is the thing you hate the most about yourself and why?
- Do you like old people or do you think they are a burden?
- How many times have you fallen deeply in love?
- What’s your opinion on “the first impression”? What was your first impression of me?
- What’s the worst thing you have ever done to your close friend?
- What’s the worst thing your best friend did to you?
- If you have to lose one of your sense, which one would you choose and why?
- Which song best describes you and your life?
- Do you think social media ruins relationship?
- What things offend you the most?
- Is there anything that you wouldn’t want your family to know?
- Have you ever rehearsed before making a phone call to your loved one?
- Is privacy a right or a privilege?
- What do you do when you’re in a bad mood, do you prefer to stay alone or have someone to cheer you up?
- Are you financially stable?
- What’s the first thing you do when you’re angry?
- Do you have any bad habits? What did you do to overcome it?
- How would you describe a perfect life?
Romantic Questions To Ask A Guy
- Do you remember your first kiss?
- If you want to have sex with anyone, who would you choose?
- How romantic are you?
- Do you like a romantic movie?
- Would you like to cook a romantic dinner for me or take me to some fancy restaurant?
- What’s the most romantic thing that you can do for a woman?
- What’s the most romantic thing a woman has ever done for you?
- What do you think who enjoy sex more: men or women?
- Are you friends with any of your ex-girlfriend? What do you think is it a good idea to be friend with your ex?
- What kind of music do you like and why?
- How do you define intimacy?
- At what point, do you think that a guy and a girl should be intimate?
- What are the qualities do you like/ dislike about me?
- Do you think about me when we’re not together?
- What song do you listen to when you think of me?
- What do you hope for a dream date?
- What do you use the most, your head or your heart?
- What was your first sexual experience?
- What would be your ideal romantic date?
- What are your thoughts about Valentine’s day?
- How would you describe me in a word?
- Do you feel complete with me?
- Are you comfortable around me?
- Is there any particular song that reminds you of me? If yes, which one?
- What is the wildest thing you want to do with me?
- Which quality of mine do you admire the most?
- Do you want to get married? Do you see us ever getting married?
- What is the right age to get married?
- Do you love kids? How many kids do you want?
- What is true love? Do you believe in love at first sight?
- What is your favorite kind of kiss?
- Would you still love me when I’m no longer young and beautiful?
- How would you define a “perfect relationship”?
- According to you, what is the best way to show love?
- Do you want to spend the rest of the life with me?
- Would you like to spend the rest of your life with me? Why?
- Would you give your life to save mine?
- What’s your favorite memory of our relationship so far?
- Do I make you happy?
- If my feet were hurt, would you carry me in your hand?
- If I wish to have ice cream in the middle of the night, would you bring it for me?
- If we get married, where would you take me for our honeymoon?
- Would you sacrifice anything to keep our relationship going?
- What’s your favorite way to receive/show affection?
- Do you believe there is one person you’re meant to be with?
- What’s one similarity between us that you love?
- Are there any secrets that you wanted to tell me, but haven’t?
- If our relationship ended, what’s one thing you would miss the most?
- How do you feel when I’m not with you? (we’re apart)
- If I had to shift to another city, would you come with me?
- What did you think of me on our first meeting?
Deep Questions To Ask A Guy
- If you have to choose between your best friends and your love, who would you choose and why?
- Is it better to marry a girl who comes from a wealthy family or not?
- What’s your opinion about marriage? Do you think, it’s just a contract or more than that?
- Do you believe, arranged marriage is better than a love marriage?
- How much do physical appearance matter to you in choosing a life partner?
- Would you leave me for anybody closer to your life (including family, or friends)?
- How do you see the glass: half full or half empty?
- Are you optimistic or pessimistic about your future?
- Do you consider yourself a happy and successful person?
- Do you believe that women should always earn less than her men?
- How do you deal with failure?
- Do you consider yourself materialistic?
- If you could live in any period of history, which would it be and why?
- If you were told to have an incurable illness, how would you react?
- If there was an emergency kidney transplantation in your family and you were only the match, would you give your kidney?
- If you could be famous for one thing, what would it be?
- If you found that your neighbor is abusing their child, do you call the police or ignore?
- If you could change one thing about yourself, what would it be and why?
- When things break, do you prefer to fix them or replace them?
- What are you ashamed of in your life?
- Do you believe in a soulmate? Are you searching for your soulmate?
- What is more precious, money or love?
- Can a positive attitude turn every bad situation into a good one?
- Do you believe in the phrase “opposite attracts”?
- Would you risk your life for someone you love?
- What role do love, affection, and attraction play in your life?
- If you die tonight, is there anything that you’d regret most?
- Is there any problem you’re dealing with right now?
- Which is correct, doing the right thing or doing things right? Why?
- Have you ever cried in front of another person?
- What would you do if you lost your job?
- What was the proudest moment that you would cherish throughout your life?
- What do you think about the purpose of life?
- What and whom are you afraid of losing in your life?
- What is your aim in life? How are you planning to achieve it?
- Do you believe in “Karma”?
- In your opinion, how important is a commitment in a relationship?
- Do you think a single life is enough to live out all the dreams?
- Does time or the situations change a person?
- Are you afraid of death?
- Are you obsessed with something?
- What do you take for granted in your daily life?
- What are the five most beautiful things in the world to you?
- Do you believe in heaven and hell?
- Which is more important to you; what you say or how you say it?
- If your ex-girlfriend wants to come back, what would you do?
- Do you think the past affects your present relationship?
- What one important lesson your ex-girlfriend taught you?
- Would you forgive a person who cheated on you?
- What would you do if your parents don’t like your partner?
- What is more important, relationship or career?
- Does it matter if I had a serious intimate relationship in the past?
General Tips
Here are some guidelines to follow with these questions to ask a guy:
- While having a conversation with a guy you’re interested in start with open-ended questions. If you ask tricky ones, then your conversations may end with simply yes or no.
- Always listen to his answers intently. It’ll help to build your ability to ask more relevant questions increases.
- Don’t pretend to be someone you’re not as it ’ll never work. While having a conversation, you need to be yourself. Never try to mold your personality.
- Never ask questions that you may not answer yourself. As this conversation must go in a balanced way, you both should involve in equal form. So, whatever questions you’ve decided to ask him, be prepared to answer your questions as well.
- Learn to respect his opinion. If he says something you don’t like, or you don’t agree then don’t get offended. If this isn’t the kind of guy you will date, never end a potential friendship. Who knows? May he has a friend who is actually like you!
- Finally, let him ask you questions too. The conversations should be in both directions. So you can include some questions that allow you to talk about yourself. In this process, you both will get closer and strengthen your emotional bond.
Final Say
When you’re in a relationship, you spend a lot of time with your partner. You can have endless conversations about family, friends, work, love, and future.
However, it is difficult to have a conversation with a guy you have just met. You might not know the appropriate questions to ask a guy.
We hope these questions will turn a bliss to create a good bond with your guy.
You also need to be prepared to answer his questions.
Have a great time!