Questions to Ask a Guy

Questions to Ask a Guy You Like That Will Blow His Mind

Questions to Ask a Guy You Like That Will Blow His Mind

Here’s a list of interesting questions to ask a guy. They’re meant to create a fascinating conversation. Remember that every guy is different, so pick and choose which questions you think might work best for your guy or questions to which you really want the answers. You’d be surprised at what kinds of questions a guy enjoys answering. So, even if a question appears to be something he isn’t interested in, it’s worth a shot.


It can be difficult to come up with questions to ask a guy when it comes to conversation openers and topics to discuss. It takes time and effort to get to know someone, and dating may be stressful. There are numerous wonderful questions to ask that will keep the conversation engaging and exciting, whether you’re going on a first date and want interesting things to say or prefer hilarious themes to spice up an existing relationship.

To truly get to know a guy and assess whether he would be a good match for you, you may wish to ask personal and meaningful questions. Some girls like sensual and dirty questions to keep things sexy because all they want is a fling, while others require simple and unique conversation starters with a guy they like. What you discuss will be determined by your relationship goals and personality, as well as the guy’s interests and hobbies.

What to be Mindful of When Asking Questions

While having interesting subjects and things to talk about might be beneficial, it’s also crucial to keep context and timing in mind. You’ll want to pay attention to the guy’s reactions and comments to distinguish between a random notion and an unsuitable question at the time. When speaking with a new guy, take it slowly and cover the basics without resorting to small talk. Don’t bombard him with questions all at once. Good connections develop organically, and with so many intriguing topics to discuss, striking up a fantastic discussion in person, via text, or over the phone should be simple.

When it comes to asking someone a question, timing is everything. Sure, a question can be random at any time and in any place. However, there is a distinction to be made between a random question and one that is asked at an inopportune time.

We’ve put together a list of the finest questions to ask a guy to give you some ideas. Explore the greatest questions to ask a guy you like to get to know him and keep the discussion going, from profound themes to lighthearted topics. Before we begin, remember to ask a lot of follow-up questions to learn more and continue the conversation.

Similarly, you should read the environment. Don’t abruptly shift the subject or barrage, someone, with questions. This isn’t an interrogation, but rather a discussion. And talks necessitate some back-and-forth between participants.

As a result, make sure your questions set the tone for a productive conversation. Of course, once you’ve gone through this list, you’ll have plenty of material to chat about for the rest of the night.

Top 30 Questions to Ask from a Guy

If you’re looking for topics to discuss in order to keep the discussion interesting and fresh, these are some of the finest questions to ask a guy. Some themes are acceptable for a first date or online conversation, while others can serve as a starting point for a conversation with a friend with whom you may have felt. While you’ll have to decide which themes are right for you, these questions will provide you with some entertaining suggestions.

What are three words you would use to describe yourself?

The three-word game always yields intriguing results and should give you a good understanding of a man’s self-perception. If he describes himself as brilliant or witty, make a point of complimenting him on these qualities later on. He’ll be overjoyed with the compliment!

What’s the nicest thing you’ve ever done for a woman?

Although you should be careful not to use this to lower a man’s expectations, it is a good question to ask if you want to understand more about a man’s generosity and respect for women. If he’s gone out of his way to make a woman happy before, he’ll most likely do it again!

What do you look for in a girl?

Asking a guy what qualities he looks for in a woman can be a bit awkward. Knowing what he values, on the other hand, can help you determine if you and his ideal mate are compatible. Whether he prioritizes personality or appearance, determining his preferences early on will help you determine whether or not a relationship is worth pursuing.

Is the idea of a spontaneous date interesting to you?

Is it necessary for the man to have a plan? Is the idea of traveling wherever the wind takes you repellent to him? For some people, spontaneity is exhilarating, but for others, it is a synonym for anxiety.

What’s a topic you can never shut up about?

Listening to someone go on and on about their passions can be quite endearing. It’s always nice to know what excites someone.

What is your biggest dating deal-breaker?

It can be difficult to discuss deal-breakers in the early stages of a romance, but it’s always best to know if you guys are a good match at the outset to avoid disappointment down the line.

Do you wait for someone to tell you they love you or do you tell them right away?

Waiting for those magical three words to be spoken for the first time in a new relationship can be stressful. Knowing where he stands on expressing “I love you” early on in the relationship should help you temper your expectations. No matter how confident they appear, some guys simply don’t feel comfortable saying that crucial remark before their girlfriend.

What is something everyone always gets wrong about you?

This question should gently prod a guy into disclosing personality features that aren’t readily apparent. People might assume he’s unpleasant because of his agitated resting face, or they might think he’s a happy-go-lucky man when he’s actually an introvert. Whatever his response is, it should provide you with further insight into the real person.

Who is your role model?

Most guys aspire to be like people who have reached greatness in some way. If a celebrity’s philanthropic activity inspires him, you may have a generous man on your hands who wants to commit time to give back.

Why do you consider your best buddy to be your best friend?

The best buddy of a man is his right-hand man. Learning more about his closest friend’s attributes will make you the ideal shoulder to weep on during difficult times. Most good relationships are built on great friendships, so try to interact with the qualities that he loves in his closest friends to build a bond that will last through any storm.

What is one thing a woman can do that would instantly turn you off?

Find out what turns a guy off right away if you want to get on his good side. If you’re wanting to start a relationship with a man, you’re not going to get very far if you indulge in conduct that he despises! Any turn-offs that are inextricably linked to your personality cannot be changed, but if he despises girls who talk on their phones throughout chats, this is simply remediable.

Even if you’ve had a horrible day, what makes you smile?

Keep the answer to this question in your back pocket to instantly brighten his mood. Perhaps he enjoys taking long walks in the sunshine to lift his spirits or prefers to unwind with a trip to the movies. Whatever his response is, it provides you with excellent ammunition that will make him smile when the time comes.

What’s anything you’ve never shared with anyone?

It can be difficult to persuade men to divulge their secrets, but if they do, you could become their most trusted confidante. Regardless of how ridiculous his answer is, knowing his innermost secret will undoubtedly strengthen your friendship.

What’s your least favorite food?

You don’t want him to have to sit through a dinner full of foods he despises or to which he is allergic. Inquire about any food aversions he may have early on.

Would you mind waiting for me to finish watching the next episode of a TV show we both started Together?

Is it about you viewing the show or about you watching the show with someone else? This is a great question to ask because, while you want him to say, “Of course, I’ll wait for you,” it’s not a big deal if he doesn’t.

What’s the next major or minor objective you want to achieve in your life?

Setting personal objectives is a crucial step in developing self-control and perseverance in life. The goals he sets for himself, no matter how big or small, show that he is committed to developing himself throughout his life.

What’s your favorite food or type of cuisine?

Date night becomes a whole lot easier when you know what his favorite cuisine is. To win brownie points with your beau, you can even cook a homemade meal featuring his most beloved dishes. Just don’t forget dessert!

What’s something that always makes you mad?

It’s never a good feeling when you make someone angry. To keep your relationship easy and breezy, discover what makes a guy mad. Whether your guy is annoyed by slow walkers on narrow streets or simply hates being texted too much, it’s best to avoid pushing his buttons if you can.

Who or what is your nemesis?

We all have things or persons in our lives that we despise. I’m sure he does, as well. And, since everyone enjoys talking about their pet peeves, this is a terrific way to start a conversation. You can promote hilarious or stupid responses if you wish to, such as jars that won’t open or YouTube movies that load adverts but not the video. You can simply shift the subject to a lighter tirade about things that irritate you.

What’s the worst and best thing about being male?

How well do you understand what it’s like to be a man? Now is your opportunity to learn more. I think you’ll be shocked by some of the responses you get from the person you’re speaking with. You might also try changing the subject to some little annoyances that come with being a man. This question is fantastic since it’s a lot of fun to answer and you’ll almost certainly learn something new.

What childish thing do you still enjoy?

We all have items from our youth that we still have, and I’m sure he does as well. He may deny it, but he still enjoys peeing in the snow and constructing sandcastles. This question is likely to get some amusing responses. Remember that you don’t have to limit it to just one childish thing; you can get him to come up with a longer list.

Do you have any customs in your family?

Inquiring about his family’s customs will lead to a plethora of conversation topics. At different seasons of the year, you can learn more about his family, views, and what to expect from him.

What’s the nicest thing a woman has ever done for you?

This is a conversation that will allow you to measure up, whether it was tutoring him for an important class or giving him the right gift for his birthday. You don’t have to match his incredible experience, but the gesture he mentions can reveal a lot about how others view him.

What do you think is the most impressive thing you’ve ever done?

A man enjoys bragging about his achievements, so give him time in a conversation to talk about the most spectacular thing he’s ever accomplished. This will not only allow him to shine, but it will also reveal the type of person he is.

What do you think is something that reveals a lot about a person you’re dating?

Perhaps he believes your charitable work indicates a lot about your kind nature, or that your rigors gym routine reveals a determined attitude. This question’s response is likely to vary, so pay attention.

What’s the most trouble you’ve ever gotten in with your parents?

With this leading question, you’ll be able to see how far you can push his people. If your sweetheart was chastised for staying out ten minutes past curfew when he was just stopped in downtown traffic, you’re dealing with strict parents who you should approach with caution.

What is the biggest argument you’ve ever had with your parents?

Is he a horrible kid, or are his parents being overprotective? This is also an opportunity to learn more about his family without having to ask a direct question.

What is one thing you never get bored of?

Is it a long summer stroll or a marathon session of video games? Something a man never tires of reveals a lot about his interests and hobbies. If you have the opportunity, recommend that you do one of these things together. Your willingness to be a part of his world will undoubtedly be appreciated.

How do you relax after a stressful day?

Everyone has different routines when it comes to winding down. If he likes an ice-cold beer along with some quiet contemplation time, you’ll know to give him space after a stressful day.

What were you like in school?

Is he the class clown, the jock, the nerd, or simply a regular guy? This is your chance to get to know a side of him you’ve never seen before. Would you get along if you had met as classmates years ago? It’s absolutely something to consider.

Best Flirty Questions to Ask from a Guy

What would happen on a perfect date night?

This not only serves as a terrific discussion starter when you’re out of ideas, but it also motivates you both to arrange an amazing date that you’ll both thoroughly enjoy. If he says something really corny, a little light teasing won’t hurt!

What did you first notice about me?

Was it your eyes? Your confidence? What made him want to reach out to you?

have you told your friends about us?

If he hasn’t told his friends about you yet, you can tell how serious he is about you. Of course, if he hasn’t, it’s only a matter of time. Maybe he’s taking it easy.

What do you like the most about me?

Finding out what a guy likes most about you can set you up for success in a relationship. If he loves your unwavering positivity or sense of humor, then you can use these traits to your advantage when he’s feeling down.

Do you think about me when you’re alone?

Put him on the spot and find out if he stays distracted by you even when you aren’t around.

What do you find most attractive about a woman?

You can quietly ask a guy what he finds most beautiful about a woman if you’re flirting with him. You can play up the aspects that he prefers based on his response to get in his good books and captivate his attention.

What do you think the best thing about being in a relationship is?

It’s crucial to understand what they value in a relationship, whether it’s unending support or consistent intimacy. Maintaining a healthy and happy partnership requires frequent discussions about your expectations.

Do you like it when a girl makes the first move?

Is he old-fashioned or does he like a confident girl with the drive?

Were you nervous when you first talked to me?

Harmless teasing is a great way to flirt. So, ask him if you make him nervous and put the pressure on him a little more.

What’s your favorite kind of date?

Is he more interested in romantic dinners, casual movie dates, or something more adventurous? This inquiry is a nice segue if he hasn’t asked you out yet.

What do you expect from a relationship?

You and your crush may just be incompatible if he or she prefers to keep things casual while you prefer to settle down. If your expectations are aligned, you may work together to become the power couple that everyone envies.

What are some of your non-negotiable boundaries?

You should never cross someone’s clearly defined limits out of respect. He may despise the fact that you still email your ex, much as girls may be uncomfortable with their boyfriend frequenting strip joints. You’ll have fewer conflicts if you and your partner establish clear boundaries from the start.

What is one thing a woman may do to turn you off instantly?

Find out what turns a guy off right away if you want to get on his good side. If you’re wanting to start a relationship with a man, you’re not going to get very far if you indulge in conduct that he despises! Any turn-offs that are inextricably linked to your personality cannot be changed, but if he despises girls who talk on their phones throughout chats, this is simply remediable.

What’s the biggest doubt you have?

We all have reservations. Whether those doubts are concerning the world in general or about ourselves specifically. This one can lead to a serious discussion, but voicing doubts can be a good approach for two individuals to form a close friendship.

When can I see you again?

Don’t expect a text from him if you wait by the phone. If you wish to see him again, enquire about his availability.

Questions to Ask a Guy That Will Make Him Think Deep

Ask meaningful questions if you want to actually get to know a guy. You’ll gain a better understanding of why he is the way he is.

Are you receptive to new ideas and viewpoints?

A person with a high level of emotional maturity can listen to other people’s ideas and viewpoints without becoming enraged. Determine whether he is open to new ideas and willing to change his mind in light of new knowledge.

Who do you admire most in life?

It’s crucial to understand who he admires in life. His response may reveal a lot about who he wishes to become. Is it a relative or a well-known person? What is it about them that he admires?

What made you choose your career path?

Did he stumble upon his current job or is it his dream career path?

What is something you try to do to make the world a better place?

What does he do to make the world a better place? Is he a litter picker, recycler, or shelter volunteer? Perhaps you could set up a date to give back to society as a couple.

Do you enjoy political debates or do you prefer to stay away from them?

Before you jump into a talk about a touchy subject like politics, you should find out how he feels about it. If you don’t want to get into a debate, avoid talking about politics until you know if it’s his cup of tea.

What does emotional maturity mean to you?

You might have a different concept of emotional development than he does. By openly asking him what he considers maturity, you can learn more about him.

Have you ever had your heart broken by someone?

It’s not easy to end a relationship. Having your heart shattered can change you for the rest of your life. Inquire about his previous romantic relationships to see whether he’s been hurt previously.

Have you ever hurt someone else’s feelings?

Has he ever had to break up with someone and left them heartbroken as a result of it? How did he bring everything to a close?

Have you ever been in love?

Being in love and loving someone are two distinct things. Being in love is a special experience, and you just know when it happens. Has he ever had a crush on someone?

What do you want to be remembered for after you die?

Is he looking to leave a large legacy or merely to be remembered as a good man?

Do you believe in a higher power? 

Religion, like politics, is a sensitive topic for some. It’s good to know where people stand to avoid offending their beliefs.

Would you alter your own past if you had the ability to do so?

He has the ability to change his past, but everything else would change as well. How would he deal with the upheaval in his own life?

Are you more of a free spirit or do you prefer to stick to a routine?

Does he need a plan? Or does he just go with the flow?

Should men and women play different roles in a partnership, or should it be dependent on each person’s unique skills and weaknesses?

Find out what he thinks about gender roles and what he thinks about them. Is he a believer in women in the kitchen or would he like to see the glass ceiling shattered?

What do you expect from a relationship?

Is he seeking a long-term relationship or just some fun? What does he consider a relationship to be, and what does he anticipate from you if you begin dating?

Interesting Questions to Ask from a Guy

Interesting questions are a terrific way to show a guy that you’re interested to talk to, making you more appealing to him. Ask a guy these great questions to get him talking about his interests and passions when you want to spice up the discussion and keep it interesting.

What is your most crazy ability?

Special abilities are always appealing, but it’s the unusual ones that can take our breath away! It may not be a particularly useful or spectacular skill, but it does reveal another aspect of his nature.

Which celebrity do you most want to meet?

The response a man gives to this question will be closely related to his interests. You’ll learn more about his objectives and the individuals he admires, which will help you decide if he’s a compatible mate, whether he’d like to trade jokes with Dave Chappelle or get exercise advice from Dwayne Johnson. In the interim, it will be interesting to converse with him about a subject that he is interested in.

What have you accomplished that you are really proud of?

Talking up a guy’s accomplishments will make him feel great and will strengthen your bond even more. You can remind him of the time he aced that major job interview or stepped in to aid a close buddy in need when he’s low.

What’s something on your bucket list that you’d like to check off as soon as possible?

When we’re just trying to get by, it’s difficult to find time to pursue our wildest aspirations. Ask him something he’d like to cross off that all-important list shortly to give him a push. Set a deadline for him and stick to it together!

Who would you like to meet if you had the chance to meet a deceased celebrity?

Your guy’s choice of celebrity will reveal a lot about their passions and interests. Famous personalities may be of interest to history fans, while fledgling artists may seek advice from artists who defined a generation.

As a kid, what was your favorite candy or treat?

Nostalgia is a strong emotion, so don’t be shy about talking about your favorite sweet delights from back in the day. There’s a strong probability he remembers popping candy and oddly flavored jellybeans as well!

What is the most memorable vacation you’ve ever had?

Finding out about your guy’s most memorable vacation can offer you a good indication of how he spends his free time. Keep in mind that what one guy finds cool may be repulsive to another. Prepare for everything from a trip to Disney World to a train ride across continental Europe, depending on his personality.

What is your earliest recollection from childhood?

Although our earliest memories are often hazy and untrustworthy, some people have strong memories of their childhood. If a recollection stands out, it most often refers to either a horrific or extremely good experience. You should tread carefully here in case you accidentally hit a nerve.

What are the worst and best aspects of being a man?

Be prepared for some belly laughs if you say something like this. Be open to his energy and share something equally challenging about being a woman if he responds with anything more meaningful or troubling.

Do you want to find true love right now or win the lottery next year?

There’s nothing wrong with being driven by money, but there’s something special in prioritizing love over wealth. If you’re looking for a hopeless romantic, a man’s response to this question will help you determine whether you’re dealing with one.

What is one aspect of your current location that you adore?

Everyone has a favorite little corner coffee shop. Learn about his favorite neighborhood hangouts and offer to go with him the next time you’re free.

Would you rather spend another decade with your partner or a single night with your famous crush?

Keep this conversation lighthearted and fun! It’s unlikely that any male would declare they’d trade you in for a superstar, so keep it funny and fun! But keep in mind that celebrity hall passes are there for a purpose!

What’s your sexiest fetish?

In the bedroom, he could be a bit bland. If he isn’t, use the opportunity to enquire about his kinkiest turn-on, which will spice things up. Sexual compatibility is essential for every successful relationship, so don’t be hesitant to push your chats and learn what he enjoys.

What was your most memorable “drop the mic” moment?

Is there an instance when he stood up for a stranger at the local coffee shop or called out inappropriate behavior at work? Whatever it is, he’ll be proud of his victory over adversity.

What three wishes would you make if you had three?

When you ask someone what they would want if they could have anything in the world, you might learn a lot about their priorities. You’ll know you’ve got a stand-up guy on your hands if he says he’d cure world hunger, work for peace, and make a farewell wish to his parents.

As a kid, what was your favourite cartoon?

Breaking the ice by talking about your early recollections is a terrific way to start. Your nostalgic conversation should naturally lead to a discussion about your childhood experiences and how they shaped you as an adult.

Is there music that brings back memories for you every time you hear it?

You can both laugh about this for days if a guy unashamedly listened to Carrie Underwood’s “Before He Cheats” after a horrible breakup. Songs, on the other hand, are a powerful way for us to connect to specific events in our lives, so he might have a song that speaks to his sensitive nature in a different manner.

What do you think would be the most romantic vacation destination?

While lying under the stars in Barbados or exploring Scotland’s beautiful lochs maybe your idea of romantic bliss, they may not be his style. In order to get a better idea of what your next vacation will entail, ask him for specifics on what he considers romantic and try to make it happen.

What is the riskiest situation you’ve ever encountered?

Despite the fact that some perilous situations are completely optional, some guys have had terrifying experiences that make for amazing stories. Allow him to tell you about a time when he was in real danger.

Have you ever told a little untruth that quickly escalated?

Even the most upright guys have told white lies at some point in their lives. Maybe he called in sick for a baseball game or told his mother how much he appreciated her gift, and now he has to wear an ugly Christmas sweater every year. Whatever he says, it’ll be thought-provoking and entertaining.

Best 35 Questions to Ask on a Personal Level

If you want to learn more about a guy you like, you should ask him personal questions that go beyond the surface. You’ll need to work these ideas into a conversation naturally while talking about personal matters, making sure the time, place, and mood are appropriate. To be successful, you must read the room, create the tone, avoid abruptly shifting topics, and allow for some back-and-forth while weaving your questions into the discourse.

What was the first thing you noticed about me?

While it may appear that you’re looking for praises, learning what people notice first about you may be both interesting and affirming. You’ll get a fascinating peek into how others view you, whether it’s your eyes, legs, or bright personality.

Are you still close to an ex-girlfriend?

There’s nothing wrong with keeping in touch with an ex-boyfriend or ex-girlfriend. However, knowing whether or not someone you’re dating is close with their ex-partner is always a good idea. It could just indicate that he is a great person who views his ex as a person, not just someone he dated.

Who was your first kiss?

Was it a playground friend or his first crush?

What are your thoughts on cheating? Is it going to damage everything, or will people be able to recover?

For most people, cheating is a deal-breaker. Is that, however, something he can overlook if he truly cares for someone?

Have you ever had a girlfriend get in the way of your group of friends?

Find out if he’s ever had a girl in his friend group, such as Yoko Ono.

What would you say to a girl if you were going to let her down easy?

When he knows he’s going to injure someone, how compassionate can he be?

Have you ever ghosted a female and if so, why did you do it?

This 21st-century response to disinterest is known as ghosting, left on reading, or whatever you want to call it. Has he ever simply ceased communicating with a girl he dated? How did he react to that?

What are your thoughts on PDA?

If a guy isn’t used to PDA (public display of affection), you don’t want to be planting kisses on him. Check what he’s okay with before you start making out in public. If you’re unsure, keep it private!

Which of your childhood memories is your favorite?

Learn more about his childhood and how he grew up. His charming tales of a bygone era will undoubtedly link you on a deeper level and should provide you with additional knowledge on his family.

What was the most embarrassing experience you had as a kid?

Everyone has a humiliating schoolyard story that they still shudder over, no matter how wonderful they were as kids.

Have you ever had a falling out with a friend? Can I ask what happened?

It can be tougher to lose a buddy than it is to break up with someone. We think about the prospect of a breakup, but we don’t think about friendships until it happens.

What is one thing that consistently irritates you?

When you’re trying to relieve tension, knowing what makes his pressure gauge go from zero to one hundred will come in handy. Every relationship will face disagreement at some point, so avoiding language or acts that irritate him will result in fewer arguments and fewer repercussions.

What would you change about one moment in your life if you could?

Even the world’s most successful people have regrets. Finding out what he wishes he could change about his past may expose facets of his personality you may not have seen at first. Encourage him not to linger on it too much if at all possible, as the event molded him into the great guy he is now.

Have you ever had a friend betray you?

Being betrayed by someone you care about is like being stabbed in the stomach. Even if he doesn’t want to talk about it too much, understanding his biggest betrayal can help you avoid making the same mistakes in the future.

Do you like to give or receive?

He may prefer to receive things rather than give them, depending on his love language. Some guys, on the other hand, enjoy showering girls with gifts. Ask this inquiry gently to see what you can expect down the road to keep your expectations in check.

What percentage of your time do you spend watching porn?

Depending on the person involved, pornography can make or break a relationship. If his porn intake is too severe for you, set some ground rules to minimize conflict or mistrust as your relationship continues.

What are you concerned about?

You’ll be able to be his guiding light and voice of reason if you know what keeps him awake at night. Often, all someone needs is a little support to face their worst fears.

Who have you entirely lost faith in?

Knowing what makes someone lose their respect, whether it’s a superstar or someone close to them, is crucial. If you don’t want to fall out of his good graces, don’t act like his worst offender!

When do you know a woman is ready to meet your family?

For any partner, meeting the parents may be a nerve-wracking encounter. When you ask when he believes it’s acceptable to meet the parents, you’ll be able to better control your expectations and prepare for when the moment comes.

What’s the dirtiest thing you’ve ever done during a sexual encounter?

If you’re in a sexual relationship with a man, you should delve deeper into his preferences and previous encounters. If his most disgusting encounter grossed him out, cross it off your bedroom bucket list.

Do you keep in touch with an ex-girlfriend?

You may or may not be comfortable with a man communicating with his ex depending on your relationship history. If this is a difficult limit for you, talk about it with your boyfriend or think about whether moving forwards together is in your best interests.

Which of your physical characteristics do you take pride in the most?

When a man is sad, knowing what he likes about himself will help you out. Not only will complimenting his best physical characteristics offer him a boost, but it will also help you figure out which areas to concentrate on during foreplay.

Have you ever ghosted a female and if so, why did you do it?

It’s unsurprising that ghosting is rather common in a world of dating apps and blind encounters. Although asking this question may be difficult, it’s important to know if there’s a danger your dream man would vanish without warning.

What’s something you’ve kept hidden from your family?

Oversharing may be a problem for a man who tells his family every detail of his life. You can utilize his response to learn about his boundaries and gain some insider information.

Have you ever dated a friend’s ex-boyfriend or girlfriend?

It’s always enjoyable to taunt a guy for dating his friend’s ex, even if he may respond shyly. Just keep in mind that this normally goes against the unwritten guy code, so if he does it, it could reveal flaws in his moral compass.

What did you take for granted in your previous relationship?

Every relationship must end in order for you to meet the one. Check in to see what he takes for granted in his relationships to avoid feeling the same disappointments as his ex.

Are you easily offended?

It’s impossible to have fruitful discussions with someone who takes offense to everything you say. It’s important to know how often your partner takes things seriously in order to avoid walking on eggshells.

What brings you the most comfort?

Finding out what makes a guy happy, whether it’s a cup of hot cocoa or a Netflix binge, will help you brighten up his dark days.

When was the last time you truly pushed yourself outside of your comfort zone?

Discuss a period when he opted to shoot his shot since courage and risk-taking are appealing attributes in guys. You never know what you’ll hear about how he acquired his present job, met his best buddy, or decided to come up to you and talk!

What is your favorite sinful pleasure?

If he enjoys dancing to Britney’s Greatest Hits on a Saturday night, you should be aware of this right away. It’s a great idea to indulge your addiction as a couple if you share a guilty pleasure.

When you’re bored, what do you daydream about?

Daydreams don’t always mirror our inner thoughts, but they frequently allude to our ambitions, desires, and dreams. You’ll know you’re one of his more trusted buddies if he can openly discuss his daydreams without feeling embarrassed.

What is the most bizarre thing you’ve ever done?

This doesn’t have to be about a romance; it might be anything from breaking curfew to stealing bottles from a liquor store. This should indicate whether you’re dealing with a bad lad or a true gentleman.

How frequently do you get to see your family?

Is he in touch with his family on a regular basis? Is he making an effort to see them on a regular basis, or do they reside in a different part of town?

Do you ever plan on marrying?

Is he squirming at the mention of marriage, or does he know what he wants from a healthy relationship?

What was the most recent music or film that made you cry?

Find out more about his vulnerable side. When someone admits to being emotional, it helps to humanize them.

Best Funny Questions to Ask from a Guy

Funny questions can help break the ice and start interesting conversations that will keep him interested and laughing. These lighthearted themes will also help him relax, participate more fully in the conversation, and open up to you. These goofy and joyful questions to ask are a solid idea if you want to reduce social anxiety and ensure a guy enjoys chatting to you.

What is one thing you’ve never been very good at?

Maybe he’s afraid of public speaking or just can’t grasp the concept of ballroom dancing. Whatever it is, his response will undoubtedly surprise you! After all, few people go out of their way to flaunt their flaws.

Do you sing in the shower?

If he sings in the shower, his expression will most likely reveal himself before he responds to your query.

What is the most ridiculous thing you’ve ever witnessed?

People are fascinating animals, and he’s probably witnessed some unusual behavior in town. Retell your experiences and giggle at the strange, wonderful, and dumb people who walk the earth and make life enjoyable and amusing.

What’s the strangest thing that’s ever happened on a date to you?

Not every date goes off without a hitch. Inquire about his strangest encounters if you want to spice up your dates together. It will also assist you in determining which dating behaviors to avoid!

What is the most ridiculous pick-up line you’ve ever heard?

Pick-up lines that are ridiculous are always a good approach to start a conversation. You two can take turns offering bad pick-up lines until you both beg for mercy, despite the fact that they’re rarely effective.

What is the most amusing thing that has ever happened to you?

A hilarious story may brighten anyone’s day. To learn more about each other, ask him to tell you about the funniest thing that has ever happened to him. There’s bound to be a great tale behind it, so pay attention!

What or person do you believe you may have been in a previous life?

If he’s interested in spirituality and reincarnation, ask him about his previous existence. You might just be able to connect the intriguing dots and convert to a believer.

Have you ever been escorted out of a public location?

Being thrown out of a place can be humiliating, and there’s typically a humorous story to go along with it. This question will undoubtedly reveal his wild side, whether he was sent out for being too intoxicated or simply trying too hard to pet a stranger’s dog.

What’s the best corny joke you’ve ever heard?

Allow him to express his goofy side by asking for his corniest joke. It’s unlikely to be humorous, but you’ll almost certainly be able to respond with a polite laugh! Feel free to share your own once he’s finished.

What’s the most embarrassing thing you’ve ever done on a dare?

What horrors has he experienced as a result of a game of truth or dare?

Would you share your most recent Google search history without feeling embarrassed?

For many people, the idea of someone searching through your internet search history is the stuff of nightmares. Could he show off his search history without making you cringe?

Have you ever experienced a 15-minute burst of fame?

Check to see whether you’re speaking with a celebrity. Discover what pushed him to fame and what spelled the end of his glory.

What’s the cheesiest line you’ve ever used on a female and it actually worked?

We’ve all heard the joke about an angel dropping from the sky and wondered if it’s ever worked in real life. Put him on the spot by asking which of his cheesy lines has been the most successful.

What would you do if the world ended in a zombie apocalypse?

Knowing how he’d react in a fight or flight situation is always useful information to have, even if it’s entirely hypothetical. This question is very engaging and enjoyable because it allows you to experiment with different scenarios and concepts.

What’s the most embarrassing thing you’ve ever done on a dare?

Because truth or dare can lead to some awkward situations, don’t be hesitant to enquire how far he’s gone in the spirit of the game. Keep it to yourself if he’s done something that’s bordering on illegal!

What’s your go-to swear word?

On a daily basis, a wealth of wonderful curse words are hurled around. Though it’s not a good idea to scream your favorites in front of others, having a private conversation about your most cathartic curse word can help to break the ice.

What is the best way to hang toilet paper?

Maybe he’s never given it much attention, but some guys are really fussy about whether they hang face-down or face-up. You’ll never be regarded as an unwelcome home guest if you learn his favorite direction.

What would you select if you could reincarnate as anything in your next life?

Reincarnation isn’t something that everyone believes in. Inquiring into what he’d like to be in a previous life is bound to be fascinating. He might wish to be free like the birds, or he might want to try to better his own life with a similar second chance.

What would you do if you were a girl for a day?

This question’s answer may be X-rated, and it can be a wonderful way to start a nasty conversation. It’s always fascinating to speculate on what the opposite sex would do if they swapped bodies for a day. Your guy’s priorities and ideas will be revealed by whether he focuses on the physical parts or tries to get inside a woman’s mind.

Which film do you believe is superior to the book it is based on?

It’s generally said that the book is superior to the film adaptation. That isn’t always the case, though. Find out whether he has a favorite movie that he likes over the book adaptation.

Weird Questions to Ask from a Guy

You might try asking these strange questions for interesting and unusual topic ideas that work. The majority of men dislike talking about the same topics over and over. Use these unique conversation starters and subjects to get him talking when you’re stuck.

What childhood pastime has been entirely spoiled for today’s children?

With each decade, new ways to play emerge. Not every new game or activity, however, outperforms its predecessor. Discover what he believes has been damaged for today’s children and spend time reminiscing about the good old days!

When you play, what game do you absolutely dominate?

Allow him to demonstrate his abilities by describing his brilliant game strategies. Whether he succeeds at board games or electronic games, you can bet he’ll teach you a thing or two about how to beat the competition.

Which of your dreams has been the most intriguing?

Our subconscious mind is often reflected in our dreams, and they can reveal a lot about our goals and dreams. Finding out about his most interesting dream may lead to a discussion about his deeper, more hidden wants, even if they aren’t always meaningful.

When you were in elementary school, what did you normally do during recess?

What you can learn about your guy’s hobbies, personality, and social presence by looking at how he spent his time in school. Inquire about his transformation if he was shy and anxious before and is now brave and daring. Some of the men may have been extroverted kids before a catastrophic occurrence ruined their life.

What piece of tech do you hope is invented in your lifetime?

Another topic that’s a lot of fun to talk about. In science fiction and your own imagination, there are a plethora of options. And who doesn’t enjoy fantasizing about the world of tomorrow and how fantastic it will be?

What is the ugliest item you own that you still cherish?

It is not necessary for sentimental goods to be beautiful to be loved. If you learn that he still sleeps with a teddy bear that he received when he was born, it will undoubtedly endear you to him. That bear, although having just one eye and appearing ragged, is an indication that he cherishes emotion and meaningful gifts.

On a plane, where do you prefer to sit?

Although we’d all prefer to fly First Class, most of us can’t afford it. That doesn’t rule out the possibility of learning about your partner’s seat preference! If you insist on sitting by the window, you’ll get along swimmingly with an aisle or middle-seat devotee.

Where would you wish to spend your golden years?

Because there are so many retirement possibilities, it’s usually a good idea to ask how they’d like to spend their golden years. Perhaps they’d prefer to retire by the sea or spend the rest of their lives elsewhere. If you share similar viewpoints, your relationship is likely to last a long time.

What is the location of your safe haven?

It’s wonderful to have a safe haven to retreat to when the world becomes too much. If he’s a private person, he might not share his response with you. If he does, you’ll know he trusts you with his personal information and safety.

What is the one board game that always ends badly?

Despite the fact that not all game nights end with someone flipping the board in fury, some games do bring out the worst in people. Is his family obsessive when it comes to their Monopoly property empire or aggressive when it comes to Scrabble? Whatever his response is, cross it off your list of board game alternatives to play with your friends.

Do you have a horror story about a restaurant?

Restaurant horror stories are often horrifying at the moment but humorous in retrospect. You can share anecdotes till you’re crying with laughter, whether he admits that his card was frequently denied on a first date or he had a server who was somewhat too nice.

What is the most uninteresting activity you can think of?

Because everyone has various interests, it’s important seeing if your love interest thinks your favorite hobby is a complete waste of time. If you and your partner agree on a dull activity, have some fun ripping it apart. Of course, keep it lighthearted!

What feature of your personality do you think people don’t appreciate as much as they should?

Gratitude is a curious thing, and many of us are unaware of our good fortune. Why not ask your partner this insightful question to gain his take on the world? It’ll probably tell you a lot about how he feels about basic pleasures and his current situation.

What is your favorite cereal for kids?

On a leisurely Sunday, there’s something comfortable about eating a bowl of Captain Crunch. Discuss what cereals used to get you and your partner out of bed in the morning to bring back good childhood memories!

What is the most valuable lesson your mother or father has imparted to you?

The advice you get from your parents is typically the most valuable. If he has strong family values or holds his parents in high respect, this could reveal a lot about his parenting and child-rearing style.

Which fact do you wish you hadn’t known?

His answer to this question will surely take you off guard, whether it’s a nasty fact or a horrific one! If you have any strong phobias or triggers, be sure to let him know before he responds. The last thing you want to happen is to unintentionally revisit anything from your past.

What old-fashioned method of doing things is superior to the contemporary method?

It’s time to tell some “back in my day…” stories! Or perhaps he’s simply fed up with the way things are now and want to return to a bygone era that he didn’t witness. In any case, many things are better now; nevertheless, let’s face it, some are worse.

You’ve undoubtedly heard so much about something that you feel like you’ve already seen it, whether it’s the plot of a book or a movie. So, let’s see what he hasn’t seen or read yet.

What is the most uninteresting activity you can think of?

Use your imagination with this one. Sure, you can stick to the mundane and uninteresting. But if you urge him, he’ll come up with something bizarre, anything out of the ordinary.

What is the most impressive “go to” dish you can prepare?

What kind of food can he prepare? Now is the time to find out! If you can persuade him to cook you his signature dish, you might even receive some wonderful meals.

Best Sexual Questions to Ask from a Guy

These dirty questions to ask will turn him on instantly when it comes to wicked topic ideas that will blow his head. Sexual questions are an excellent technique to take your conversation to the next level and demonstrate that you’re seriously interested in a man. While some people are uncomfortable discussing strange topics, you should realize that practically all men enjoy playing sexual games and are open to discussing them. If you’re going to discuss these topics with him, make sure you know how you feel about him first.

Which of your turn-ons is the most basic?

It’s not uncommon for what gets us in a good mood to be part of a defined standard. Consider risqué dress, sensuous caressing, and the usual suspects. Some vanilla sexual interests, on the other hand, go beyond the normal simple turn-on. Is it true that spectacles drive him insane when he sees a girl? Is there something he likes about a woman who knows her way around a car’s engine? Find out what gets him going in an unexpected way.

What’s your sexiest fetish?

Vanilla sex is on one end of the scale, while kinky sex is on the other. It’s completely great if getting down and dirty with kink isn’t for everyone. However, knowing what works for a possible sexual partner is always beneficial.

What’s the dirtiest thing you’ve ever done during a sexual encounter?

Find out how daring he is when it comes to sex. Was it a once-in-a-lifetime experience for him, or did he like his sexual experimentation?

When did you lose your virginity and when did you lose your virginity?

Did he wait till he met the right person, or did he want to get rid of his v-card as soon as possible?

Do you like to give or receive?

Inquire about his bedtime generosity. Is it more enjoyable for him to provide pleasure or to receive it?

When it comes to sleeping with a girl, how long do you generally wait?

Is he willing to wait till the third date or is he OK with a quick hookup? So you know what to expect from him as a potential companion, ask him if he has any established time frames for sleeping with someone.

Do you enjoy watching porn?

People will try to deny it, and some will argue that it is a terrible act, but a lot of porn is eaten every day. Find out if he spends any time during the day looking at or watching porn. You could even ask him to watch it with you if you’re feeling brave.

Do you have any fantasies you’d want to share with me?

Interested in seeing if he has a sexual bucket list? Inquire about his fantasies and ask if he’d like to attempt anything new with you.

What’s the furthest you’ve gone in search of a hookup?

Asking him this question will help you figure out if the distance is a barrier for him.

Have you ever texted someone a “you up” message?

The well-known booty call. At one point or another, we’ve all been there. Inquire as to whether he’s sent any hopeful late-night texts.

Do you ever send girls nudes?

What are his thoughts on sexting? If you ask him, will he send you a nasty photo via text?

What are your thoughts on vulgar talk?

Some folks have no qualms about dressing up and talking in a filthy manner. Others find it too humiliating to do so while maintaining a straight face.

Is that a gun in your pocket, or are you simply relieved to see me?

This remark was made popular by Mae West in the 1930s, and it still remains true today. Any guy you ask will give you an interesting response if you repeat this tempting quote.

Is it better to have the lights on or off?

The right mood lighting can make or break a romantic evening. But, when it comes down to it, does he keep the lights on or turn them off for the big event?

Have you ever been in a position where you were friends with benefits?

To some folks, sex is simply sex. It’s just an entertaining way to pass the time. It’s not a bad thing to have a pal with benefits. Consider it a new degree of maturity. He has the ability to put emotional attachment and envy aside.

Is it better to go early in the morning, late in the afternoon, or late at night?

Does he want to have a little fun in the afternoon, or does he prefer to wait until bedtime? Maybe he adds a little excitement to his morning ritual now and then.

How many previous sexual partners do you consider excessive?

Some people are concerned with numbers, while others are concerned with past ties. Ask him how many sexual partners he thinks are too many so you may learn more about what he thinks of you and your background.

Will you ask me inside or upstairs?

As Seinfeld’s Elaine Benes discovered in the episode “The Label Maker,” requesting to go upstairs means you’re looking for some adult pleasure. If the night is coming to an end too quickly for you, be courageous and ask him if he’ll ask you inside his apartment. Alternatively, if you’re looking for even more daring questions to ask a guy, be direct and invite him back to your place.

20 Unique Questions to Ask from a Guy

  1. What have you done that has been the most romantic thing you’ve ever done?
  2. What is it about women that you dislike?
  3. Who do you pretend to admire but secretly despise?
  4. What do you believe life’s purpose is?
  5. Do you prefer to sleep on one side or the other of the bed?
  6. How would you define the ideal kiss before entering the bedroom?
  7. Do you enjoy receiving massages?
  8. Do you ever feel shy when you’re around me?
  9. What or who do you find irresistibly seductive?
  10. Do you believe in karma, destiny, or fate?
  11. What is the location of your happy place?
  12. Do your buddies have an influence on your thoughts and decisions?
  13. What would you give your child’s or son’s name?
  14. When does it make sense to let your defences down in a relationship?
  15. Would you prefer sit in a hot tub or swim in a pool?
  16. Do you enjoy making extravagant gestures?
  17. Do you have an easy time forgiving others?
  18. What relationship advice would you give your children?
  19. Which colour do you think I’m most attractive in?
  20. Do you have any insecurities?

100 Simple Questions to Ask from a Guy

  1. What is your all-time favourite, million-times-watched film?
  2. When you were a kid, what did you want to be when you grew up?
  3. If money were no object, where would you travel on vacation if you could go anyplace in the world?
  4. How would you spend a million dollars if you won the lottery?
  5. What about a woman appeals to you the most?
  6. What is your most outrageous ability?
  7. What is one thing about you that everyone usually gets wrong?
  8. How do you unwind after a long day?
  9. Who do you look up to as a role model?
  10. Which celebrity do you most wish to meet?
  11. Is there anything you’ve never been really excellent at?
  12. What is the one thing about a woman that you always notice first?
  13. What is your favourite memory from childhood?
  14. What are you most proud of in your life?
  15. What have you done that you’re not very pleased with?
  16. Can you tell me about the scariest thing you’ve ever done?
  17. If you could be a pro athlete in any sport, which one would you choose?
  18. Who would you marry if you could marry only one celebrity?
  19. What is your best friend’s best friend’s best friend’s best friend’s best friend’s best friend’
  20. What do you consider to be the best aspect of being in a relationship?
  21. Which animal is your favourite?
  22. Is there anything on your bucket list that you’d like to cross off as soon as possible?
  23. Is there anything on your bucket list that you think you’ll never do?
  24. What’s the strangest thing that’s ever happened on a date to you?
  25. On your CV, what do you always lie about?
  26. Which show do you think you could binge-watch multiple times?
  27. What’s your favourite way to flirt?
  28. On a first date, what would be the worst thing that could happen to you?
  29. Who would you like to meet if you could meet one dead celebrity?
  30. Who is your favourite Instagram user to follow?
  31. What is your biggest dating pet peeve?
  32. If you could change one thing about social media, what would it be?
  33. What is one thing a woman can do to impress you right away?
  34. What has been your most humiliating experience to date?
  35. What is one thing a lady may do to turn you off instantly?
  36. What’s the best praise you’ve ever received?
  37. What brings a grin to your face even when you’re having a bad day?
  38. Do you prefer to spend the rest of your life with dogs or cats?
  39. Tell me something that no one else knows about you.
  40. As a kid, what was your favourite candy or treat?
  41. What is one food that you would never eat?
  42. What do you consider to be your most attractive physical feature?
  43. What is it about me that you admire the most?
  44. What would you do if you could change jobs right now?
  45. Give them three adjectives that best describe who you are.
  46. What does your ideal date entail?
  47. What is the most exciting vacation you’ve ever experienced?
  48. Tell us about a country you’d like to visit.
  49. What are your greatest fears?
  50. Can you tell me about the nicest thing you’ve ever done for a woman?
  51. What is the most thoughtful thing a woman has done for you?
  52. What’s your biggest dating stumbling block?
  53. What is your earliest recollection of childhood?
  54. What is one item that consistently irritates you?
  55. What do you consider to be your best achievement to date?
  56. What do you like best about where you live?
  57. What is one feature about your current location that you despise?
  58. Do you have a favourite Starbucks order?
  59. What would you acquire if you could only get one present?
  60. Would you rather get a present, gift cards, or cash?
  61. Do you consider yourself to be an introvert or an extrovert?
  62. If you could go back in time and change one thing about your life, what would it be?
  63. When you need to unwind, where do you like to go?
  64. Do you prefer to work out at the gym or at home?
  65. Can you tell me about the last time you cried?
  66. Is there anything a lady can do that you will never forgive her for?
  67. Have you ever had a friend betray you?
  68. What do you enjoy most about your friends?
  69. How did your best friend and you meet?
  70. What is the first question you ask a woman on a first date?
  71. Do you want to start a family?
  72. What makes you wish to start a family?
  73. What’s the worst situation you’ve ever found yourself in?
  74. Would you prefer a beach vacation or a vacation in a cool city?
  75. What is your ideal automobile?
  76. Do you have a favourite book?
  77. Tell me about the worst movie you’ve ever seen.
  78. What superpower would you like to have?
  79. What is the most enjoyable activity you have ever shared with your friends?
  80. Do you have a stronger bond with your mother or father?
  81. Who in your family is your favourite?
  82. What do you consider to be your most outstanding accomplishment?
  83. Can you tell me about your strangest habit?
  84. What is your greatest fear?
  85. Is there anything on which you would never spend money?
  86. Do you have a yearly tradition that you look forwards to?
  87. Do you prefer the winter or the summer?
  88. Can you think of a time when you were worried about something that turned out to be insignificant?
  89. Do you believe there is anything that shows a lot about a person you’re dating?
  90. Have you ever had a crush on someone who didn’t reciprocate your feelings for you?
  91. How do you know when a woman is ready to meet your family?
  92. What would you do if you had a day off with nothing to do?
  93. Do you believe your astrological sign is correct for you?
  94. Have you ever experienced the loss of someone close to you?
  95. What three wishes would you make if you had three wishes?
  96. When you were a kid, what was your favourite cartoon?
  97. What is the most revolting food you’ve ever consumed?
  98. Would you want to play a game of truth or dare?
  99. Describe your ideal burger in 100 words or less.
  100. What have you done wrong for most of your life and only recently found out the right way to do it?

Text Message Questions To Ask from a Guy

These themes might assist in smoothing the conversation and keep things interesting if you’re looking for meaningful conversation and don’t know what questions to ask a guy through text. Even if it merely leads to friendship, texting can be a terrific method to break the ice and start a new relationship. Most guys and girls will stay up late the night before a first date to text each other, especially if they’re starting to like each other. It might be difficult to come up with topics to text about unless you’re naturally flirtatious, and this list can help you come up with some suggestions.

  1. Who is your favorite person to follow on Instagram?
  2. What do you usually like to do on the weekends?
  3. What’s the most memorable thing you’ve done so far in your life?
  4. What’s your biggest pet peeve?
  5. When you’re in a bad mood, what cheers you up?
  6. How do you feel about surprises?
  7. Which sexy scene in a movie would you want to recreate?
  8. Have you taken a Myers-Briggs personality test? If so, what’s your type?
  9. What’s the most important thing you’ve learned in life?
  10. Would you rather drink coffee or water?
  11. Do you have a real-life archnemesis?
  12. What’s the craziest place you’ve done it?
  13. What’s one thing a classy woman should never do?
  14. If your house was on fire, what’s one thing you would save?
  15. What were your favorite and least favorite subjects in school?
  16. What’s your favorite quality about yourself?
  17. What did you spend your allowance on growing up?
  18. Did you play high school or college sports?
  19. Have you ever been in a fight?
  20. Would you rather be smart and ugly or dumb and beautiful?
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Kiara Shailene

Kiara has branched out into freelancing after years of managing hundreds of fashion brands for a major store. In the United States, Canada, Australia, and the United Kingdom, we're connected to a number of fashion retailers and media platforms. As an editorial strategist for a number of online magazines, Kiara uses her experience to help growing fashion firms develop high-quality content. Her work in JazzyFeed consists of articles on Fashion, Beauty, and Lifestyle products.