Questions to Ask a Guy – Simplified Skills

For some women, approaching a man they like can be a very big obstacle, especially during a first meeting. For others, however, it might prove to be a fun thing to do. You will be better prepared to take that step by knowing exactly what questions you need to ask a man.

This article gives you a wide range of questions to do just that, so that you can approach any man and get his attention for as long as you want. When you ask a man some questions, the answers can help you learn more about his character and way of thinking. In the same way, these questions will also allow the man to learn a little more about your way of being. The questions we are going to offer you are a good way for two unknown people to open to each other.

Ladies (and gents), the following questions will help you overcome your stress and the awkward silent moments that can settle in during a conversation.

Relationship questions to ask a guy

The feelings of men are not always easy to fathom, especially when it comes to love. Do you wonder why things are not going in the right direction in your relationship? Even though you’ve been together for a long time, maybe he just does not dare to take the next step? Maybe it’s the age of your partner — since the attitude to love can change with men over the years. A man who in his twenties may still be afraid of a strong bond (or just not interested in one) can experience a change of heart starting from 30 and grow into a wonderful pater familias.

We created list of questions below because we think that they can really be of help in getting to know a guy’s point of view on relationships, even if you have not seen each other before.

What is the best way to finish a successful day?
If you inherited 10 million euros, what would you do with your life?
If you could get married with a movie character, who would it be?
What is your favorite quote?
How would you describe yourself in 3 words?
What would you do differently if you knew that no one could judge you?
What is one thing that you have never been good at?
What time of your childhood is your favorite?
If you had to lose one of your 5 senses, what would it be?
If you could make a wish what would it be?
What was the most difficult time of your life?
What attributes can make the most beautiful woman the ugliest?
Can you finish the sentence? The world would be better, if ________?
Do you believe in love at first sight?
What is the best compliment that you have ever received?
What is that something that always puts you in a good mood?
What makes you angry?
What mistake will you never make again?
What do you do as much as you can to feel good?
If you could change one thing in your life, what would it be?
What is one thing that you will never let someone do to you?
When was the last time you cried?
Do you believe in love?
What one thing aren’t you ever able to forgive?
What is the biggest lie you said?
What do you like most about your home?
What do you like most about me?
What will your life look like in a year?
What’s stressing you every time?
What was your favorite game when you were a child?

What is your biggest dream?
What is the biggest quality in a woman?
What do you like about a woman?
What is the thing you have that is most valuable to you?
What is something you never get tired of?
Do you think that social networks are a good thing or not?
If you could give one million to a charity, which would it be?
If you had to die in one month, what would be the 5 things you would do?
What is the best part of the day?

Freaky questions to ask a guy

It is man’s nature to flirt and experience not only romantic feelings but also sexual feelings. While dirty talk is not for everyone, it can be helpful in several ways. Whether you meet someone or are in a committed relationship, you may feel the need to ask him some uncomfortable or perverted questions. In this article, we have many examples of freaky questions that you can ask a guy.

In what kind of outfit would you like to see me?
What are you wearing right now?
What would you do if you see me naked?
What would you if I put my hands under your shirt?
Do you want a massage?
What is your favorite part of my body?
What is your biggest sexual fantasy?
Do you like the lights on or off?
What do you want to do with me right now?
What would you let me do for you?
Have you ever used lubricants?
Would you ever use edible underwear?
Do you think you could just take off my panties with your teeth?
What is your favorite lingerie?
Should I talk dirty to you now?
Do you like it when I’m naughty with you?
What if I was naked and lying in your bed?
What would you do, if I had opened the door naked?
Where do you want to kiss me?
What was your last dirty dream?
Did you ever dream of me?
What underwear color do you think I am wearing right now?
Would you ever have sex outside?
Would you ever do it in a car?
What is your favorite position?
Is there a position that you would like to try, but have not yet done so?
Do you like it when I’m in control or do you prefer to take the lead?
What do you think I should wear in bed?
What’s your favorite prelude?
Do you think I’m a good kisser?
Where do you want to touch me right now?
Did you ever want to do it in public?
Where is the most outrageous place you did it?
Would you ever want to have a threesome?
What do you think is sexy about a woman?
What is your favorite place to touch?
How would you like to be touched?
If you could only touch me in one place, where would it be?
Have you ever bought underwear for a girl?
What do you think is the sexiest thing about me?
What would you do if all my clothes were wet?
Can you unhook a bra with one hand?
Were you ever caught red-handed?

Intimate questions to ask a guy

We all have skeletons in the closet and things in our lives that we’re not comfortable answering questions about. It’s not only men that want to ask women intimate questions; there’s a high number of women, too, who want to know intimate details about a guy’s life. If you want to ask him, we are coming to the rescue with the questions below. We know that you do not always dare to ask them directly, because they are embarrassing or too personal, or because you are just afraid they are ridiculous and superfluous. We included intimate questions about sexuality and very personal questions that are complicated to address and which require openness and trust.

These are intimate questions that, in addition to illuminating the reality of our partner and transcendent intimate questions, will also help to improve communication, both emotional and sexual.

So here are some intimate questions you could ask a guy.

Is it really annoying to ask you intimate questions?
Who is your most faithful friend?
Do you consider us to be good friends?
Do you see yourself falling in love again?
I like you enough to ask you to go out with me. And you, do you appreciate me enough to say yes?
What exactly is your idea of ”the perfect girl”?
What is your biggest failure?
If you had the opportunity to do something extraordinary, what would you do?
Have you ever had strong feelings for someone?
Is your life today the way you imagined it to be 10 years ago?
If you could, what would you change in your life?
Do you like yourself? If yes, why? If not, what would you change?
Can you name 10 people in your life that you like to spend your time with?
Do you have phobias?
Can you describe the type of romantic relationship that you want to be in for the rest of your life?
What was your last relationship like?
What do you enjoy doing alone?
What was the most embarrassing moment of your life?
Do you often want to be alone for a long period of time?
If you remember your dreams, what are they mostly about?
What is your biggest regret?
Do you cry often?
Do you enjoy reading?
Do you read erotica?
How would you describe love?
Do you lie often?
What was your first impression of me?
What turns you on?
What do you usually do when you like someone?
What’s the oldest woman that you would date?
What makes you happy?
What makes you sad?
What do you like to do the most and what do you like to do when having sex?
What do you think is the key to having better sex?
Which of the senses do you stimulate the most during sex?
Are you open to different sexual practices of a couple?
What do you think is your greatest insecurity during sex?
Do you think sex transcends the physical?
How do you like sex and what points make you explode with pleasure?

Naughty questions to ask a guy

Many know that the key to happiness in a couple is communication – and intimacy, too. Being able to communicate with your partner about everything, including sex, can bring you closer and make your inner life more fun, more passionate, more inventive and more exciting.

Whether you are a long-time couple or just starting your story in pairs, these questions will help you dive into unexplored areas in your relationship and make you both the seduced and the seducer.

Because nothing is ever acquired in a couple, enjoy a short naughty interrogation to revive the flame or seduce the guy you like.

What’s the weirdest position you’ve ever tried?
Do you like to kiss during intercourse?
Do you like being loud during sex?
What kind of porn do you like?
Do you wear boxer shorts or briefs?
Do you think you could ever be a porn star?
Would you like to cuddle with me?
Have you ever received a blow job?
Would you ever have a threesome with another man?
Have you ever been in bed with a same-sex partner?
If you had to choose, would you choose breasts or butts?
Did you ever get a lap dance?
Did you ever pay for sex?
Would you ever pay for sex?
Have you ever read an erotic novel?
What’s your favorite position when you’re up?
What’s your favorite position when you’re down?
Have you ever used a toy?
When did you last play with yourself?

Would you ever want to be blindfolded?
Is there a steamy scene from a movie that you would like to recreate?
How many people did you sleep with?
Do you think you can strip naked in less than 5 seconds?
Have you ever played strip poker?
Have you ever asked an intimate question?
Do you like to do it with the clothes on or off?
Have you ever had a friend with benefits?
Do you talk much during sex?
Have you ever been with your teacher or professor?
In which outfit would you look the hottest?
Did you ever eat during foreplay?
If I had chocolate syrup and whipped cream over my naked body, would you lick it?
How do you prefer women down, shaved or completely natural?
Did you ever do 69?
Did you ever get a hand job while driving?
Did you ever go all the way on your first date?
Have you ever played with yourself more than 3 times in a day?
Have you ever made a sex video?
Would you ever want to make a sex video?
Have you ever been in an open relationship?
Do you like it when I do not wear underwear?
Have you ever done a striptease for anyone?
Do you want me to do striptease for you?
Would you ever do it during my… days?
What would you do, if you had me alone for a whole day?
Have you ever seen porn in a public place?

Questions to ask to get to know a guy

We often meet many people in our daily lives, without really being able to say that we know them well. Being aware of someone’s routine does not mean that you really know them. It often takes time to stop and talk to each other for more than five minutes.

Same goes for a first date. It is not always obvious what to ask. There are classic questions, but after knowing what he does in life, where he comes from and what his hobbies are, what else is there to know?

What do you think of at night when you go to bed?
What is your favorite family game?
In which place do you feel the best?
Who are you closest to in your family?
Are you sure of what you want to do as a job in life?
If you had to eat just one thing for a month, what would it be?
Your dream job when you were young — what was it?
Do you think you want to have children? (If yes, how many?)
Could you tell me one of your best childhood memories and one of your worst?
What is your ideal trip destination to go to?
Can you tell me the worst date that you’ve ever had?
If you had a day left to live, what would you do?
What do you like most about your best friend?
Can you name 3 movie characters / TV series that describe you perfectly?
Do you like when you are being paid a compliment, or do you become awkward every time?
Who is your favorite band or artist of all time?
Do you believe in love at first sight?
Have you ever been in love? How many times?
How are you when you are in pain of love?
What trait is capable of seducing you?
What turns you off automatically?
What would you like to accomplish one day?
What prevents you from starting to realize it today?
If you were going back to school, what do you think it would be like?
Do you like having regrets or remorse in life?
What is the most beautiful place that you visited?
Do you believe in karma?
What makes you different from others, in your opinion?
What do you think is your best quality?
How would your friends describe you?
If you had no embarrassment, what would you do?
Do you believe in soul mates?
What do you like most about being at home?
What do you like most about you that is not physical?
What’s the craziest thing that you’ve done?
What do you know that you need to improve your life?
How complicated would your life be, if you got rid of your cell phone?
What’s your favorite joke?
Do you believe in life after death, life on another planet or destiny?
What do you want to ask the opposite sex often, but you do not dare? And why?
What are you missing the most from the time you were in high school?
Why did you cry the last time?
If you’re given a week to live, what will you be doing?
If you could come back at any time in your life, not to change something, but to appreciate the moment, when would it be?

Serious questions to ask a guy

Having at least one topic of conversation to get acquainted with will help you forge new relationships that can potentially lead to strong friendships.

So, you’ve liked him for a long time, you want to get to know him and, finally, he agrees to go out with you. But now you have a new problem – what should you ask him? You’ve already asked questions about his favorite books and movies, and you’re worried that the conversation will end in silence.

Guys love to talk about themselves. Start by asking about his job. It may be boring, but he’ll feel good, because there’s someone he can talk to about what he’s doing.

If you lead the conversation with some of the questions below, you will discover the most authentic qualities of your male interest or just a male friend.

What do you do for work? Do you like it?
If you weren’t doing what you’re doing now, what job would you choose?
What was your favorite game as a child?
What’s the best advice someone has ever given you?
What was the best gift you have ever given to someone?
If you could live somewhere, where would it be?
How do you behave with people who annoy you for no reason?
When did you experience the biggest adrenaline kick?
What did you learn from your past relationships?
What’s the most important thing girls should know about guys, and it seems to you that they do not understand?
Who is your best friend?
What was the worst thing to have happened in your childhood that your parents have not found out about?
What were the moments that changed your life?
What would make a perfect day?
What are your most memorable travel experiences?
What are you most proud of?
What’s on your list of life goals?
What is the most unusual thing that you have ever done?
Do you believe in kinship? If so, is there anyone around you that you would call your soulmate?
Would you break the law to help someone you love?
In your opinion, which dream will you never be able to fulfill? Why?
If you could, would you like to know when you die?
What do you think: how does one get to be happy?
Is there life out there?
Do you usually stay friends with your exes?
What is it never too late for?
Would you give up on all your best memories, so that you can wipe out your worst?
If you could give just one piece of advice to a newborn, what would it be?
What makes you laugh? What makes you cry?
If you had to use a single word to describe yourself, which one would it be?
What are you searching for in a relationship?
Do you focus more on appearance or brain?
You can leave tomorrow for an all-paid-for trip: where would you go and with whom?

Dirty questions to ask a guy while texting

In the beginning, everything is new and exciting. How does the new man by your side react? What does he have in common with you? Where are you completely different? You want to know everything about him.

And to find out more about him, you both have all the time in the world. So, night after night, you talk about friends and hobbies, about idiosyncrasies and God and the world. The great journey of discovery has long since begun.

Yet, when it comes to the S word, many women blush and do not dare to ask sex-related, naughty questions. At least, not when they are face to face with their sexual interest. One may, however, get more courage using their phones.

So, how about a little sexy question time for you and your guy? At least as open and honest as a teen “truth or dare” game and at least as immoral as a good erotic story.

For those of you who’re more at ease with this way, we are proposing some good, dirty questions.

How was your first time?
If my hand was now under your blanket, what would it find there?
If I was with you now, what would you like us to do?
Have you ever had a one-night stand?
Do you prefer to be on top or under?
What are your secret fantasies?
Do you like threesome sex?
Are you dominant in bed?
Do you find it hot to have sex in the car?
Which sex toys have you already tried? Which toy would you like to try?
What are your top 3 erogenous zones?
Stroking, licking, sucking, nibbling – how do you prefer to be touched?
What turns you on the most?
What is your favorite position?

Where would you like to have sex?
How important is to you the orgasm of your partner?
Are you talking about sex with your friends?
Dressed up, in lingerie, panties or naked-how do you like me especially sexy?
Which of my body parts do you like the most?
Which sexual fantasy have you never told anyone about?
Is sex in front of a mirror hot to you?
Whipped cream, chocolate, strawberries. What do you think about sex and food?
If we played roles now, what would you like the scenario to be?
Do you have any fetish? If yes, what is it?

Embarrassing questions to ask a guy

There are questions in life that you do not have to ask. But you can. If you want to embarrass someone, for instance.

For those who have a wicked sense of humor, we gathered some of the best cringe-worthy questions. Not all questions need a serious conversation. Some may make you laugh, others may be thought-provoking, and others may even give you pleasure.

What is the most embarrassing thing that has ever happened to you?
Were you caught by someone while having sex?
Have you ever been skinny dipping?
What was the most embarrassing and/or crazy thing you ever did for love?
Who is your least favorite friend?
What is the longest intimate session you have ever had?
Who are your exes?
Which friends of yours are homosexuals?
What would you like to change about me?
When did you last wet your bed?
Why are you not working out?
Which girls that you know are more beautiful than me?
Have you regretted your past relationship?
How much are you making?
Which position in the Kamasutra have you already tried and which one can you recommend?
Have you ever faked an orgasm?
Have you broken the law? If so, how?
Have you tried drugs?
Have you ever driven under the influence?
Have you read 50 Shades of Gray or have you seen the movie?
How many times a week do you lie and what was the biggest lie you have ever told?
What was your biggest mistake so far?
Have you ever had a blackout because you drank too much?
Have you ever taken erotic pictures of you? If so, who did you send them to?
Have you ever stalked someone?
What was the most embarrassing thing you ever had to google?
Have you ever been kicked out from a venue?
Have you ever asked someone for their phone number and never called?
Were you dating two girls at the same time?
Whose death, of all the people in your family, would be or was most terrible for you and why?
Do you secretly know how you’d like to die?
If you could change something about the way you were raised, what would that be?
What is your most terrible memory?
How much closeness and warmth were there in your family?
What do you feel about the relationship with your mother?
Can you make three honest “We…” statements? For example, “We are both in this room and feel…”
When was the last time you cried in front of another person?
What – if anything – is too serious to joke about?
If you died tonight and you could not tell anyone else: what would you regret the most?
How many people did you sleep with?

Flirty questions to ask a guy you like

Do you want to start something, but you are not sure how to do it? It’s difficult if you like a guy. You want to chat, but you’re either too nervous to get the courage, or you’re too worried that things will get strange or that your conversation will be boring. Maybe you are too friendly instead of flirting. But those flirting questions to ask a guy will get you on the right track.

If you want to seduce a man, you want to know everything about him and to achieve this, you must ask many questions.

Be frank and direct to really find out who you want to charm. The questions to ask the guy should always be oriented, so that the discussion is not flat, that you can exchange opinions, respond and learn from each other.

Showing a guy that you’re interested in him is a little nerve-wracking. One of the less frightening possibilities is to have a flirtatious conversation with him. You do not have to go too far, just ask some silly, funny, flirting questions and see where the conversation is taking you. More importantly, see if he also starts flirting with you.

If he responds in the same way, then you know that you are a winner. If this is not the case, it is not too late to get out elegantly.

What was your best kiss?
What would you say that makes a woman beautiful?
What are you looking for in a woman? What qualities?
What did you think of me when you first met me?
Where do you like to be kissed?
What’s the most romantic thing you’ve ever done?
What would you say if I kissed you now?
Do you think of me as a friend or as someone who could be more than that?
Do you like when the girl takes the first step, or would you rather be in control?
What’s your favorite animal name that you like your girlfriend to call you?
Would you like us to go out tonight?
Do you like to hug?
Do you like to talk sexy?
Do you like massages?
Are you rather gentle or wild in bed?
What is the most unusual place where you made love?
If a beautiful stranger came to your door and wanted to make love to you, would you let her in?
Would you be turned on, if you saw me masturbating while watching porn? Would you look at me or join me?
What is the most erotic thing that a couple can do to each other?
What type of outfit would suit me best?
Have you ever been to a strip club?
Can you tell me a fantasy that you have and never told anyone?
Can you guess the color of the underwear that I am wearing now?
What would you whisper in my ear, if I kissed you now?

Good sexual questions to ask a guy

The prelude does not start in bed, but in one’s mind. Sexy questions can really spur the partner’s imagination. Sometimes you just want more than just a harmless small talk and a “How was your day, darling?”

An open conversation about erotic preferences and sex fantasies can further stimulate the love play in a relationship, make it more exciting, more passionate and more intimate, and make the partnership more intense well beyond the boundaries of the bedroom.

Through honest exchange and outspoken communication, everyone learns exactly what the other really likes.

Have you ever had a one-night stand?
What is your most intense experience?
What would you do if we were alone at home?
Do you like to talk dirty during sexual intercourse?
What should I tell you while we do it?
Do you ever watch “adult videos”?
Do you ever play with yourself?
Would you like to play with yourself now?
Can I watch you play with yourself?
Which positions have you ever tried?
Which positions would you like to try?
Do you like me up or down?
What would you do to me, if I were in your bed now?
Have you ever had phone sex?
Do you love to give or receive?
What are you most worried about?
Have you ever had an orgasm?
What do you think of me?
What do you want me to do more in bed?
Do you prefer it in the morning or just before bedtime?
What is the best thing a woman can do to you in bed?
What do you think about when you touch yourself?
What’s the hottest outfit you’ve ever seen on a woman?
How do you like being touched?
What’s an instant turn on for you?
If you could only touch me in one place for the rest of your life, where would it be?
Do you like it rough or romantic and sensual?
What’s your riskiest fantasy?
Have you ever been nude bathing?
Do you think that you were ever so loud that you woke up the neighbors?
How was your first time?
If you are still a virgin, how do you want your first time to be?
Compared to the other girls you’ve been with, what do I do best?
Have you ever been seduced by someone older than you?
Did you ever do it from behind? Did you enjoy it?
Do you like sex?
Would you rather watch someone do it or be watched?
What was your filthiest fantasy when you were at school?
Did you ever get nude pictures from someone?
Have you ever sent a naked picture of yourself to someone?
Have you ever had a quickie?
What is your favorite oral sex?
If you could do it with a porn star, who would you choose?
If you could have any celebrity, who would you choose?
Would you ever take part in an orgy?
Have you ever done it with more than one woman in a day?
Have you ever had an orgasm twice?
Were you ever tied up during sex?
Would you like to be tied up?
Have you ever made love more than once a day?

Sometimes, women would like to take things into their own hands and approach a guy who caught their interest, rather than desperately trying to send him signals. That’s the point of this article; help you ask a guy the best questions, so that you could see who he really is and if he’s friend/boyfriend/husband material.

Standard questions have their raison d’être, but you quickly realize that those questions can be boring, and he can quickly lose interest. Another cool technique is to make guesses: instead of asking him what he is studying, you can ask something like: “Your outfit has real style. I assume you have to do with fashion professionally?” We don’t want you to have those embarrassing moments of silence. Many women, if not most, do not know what to ask. It’s not okay to be getting monosyllabic answers.

The questions above are not questions that we arbitrarily thought up at our desks. No. They all have a certain sense of getting to know each other and are the result of years of dating experience that we gathered from friends, families, acquaintances.

If you want to be this self-confident woman (or man, or whatever else, we don’t judge!) who can easily and naturally ask a guy questions, read our article.