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300 Questions To Ask A Guy You Like

When it comes to conversation starters and things to talk about, it can be a challenge coming up with questions to ask a guy. Dating can be stressful and getting to know someone can take time and effort. Whether you’re going on a first date and want interesting things to say or prefer funny topics to spice up an existing relationship, there are many good questions to ask that will keep the conversation engaging and fun.

Questions To Ask A Guy Over Text

If you’re looking for meaningful discussion and don’t know what questions to ask a guy over text, these topics can help facilitate the conversation and keep things interesting. Texting can be a great way to break the ice and start a new relationship, even if it only leads to friendship. Before going on a first date, most guys and girls will stay up late to text each other, especially if they’re starting to like one another. Unless you’re naturally flirty, it can be a challenge thinking of things to talk about via text and this list can inspire you with ideas.

Questions To Ask A Guy Over Text

  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?
  21. What was your first job ever?

Unique Questions

  1. What’s the most romantic thing you’ve ever done?
  2. What’s something you don’t like about women?
  3. Who do you act nice around but secretly don’t like?
  4. What do you think the meaning of life is?
  5. Which side of the bed do you like to sleep on?
  6. How would you describe the perfect kiss that leads to the bedroom?
  7. Do you like getting massages?
  8. Do you ever get shy around me?
  9. What’s something or someone you find irresistibly sexy?
  10. Do you believe in karma, fate or destiny?
  11. Where is your happy place?
  12. Do your friends impact your opinions and decisions?
  13. What would you want to name your daughter or son?
  14. At what point in a relationship do you let your guard down?
  15. Would you rather swim in a pool or sit in a hot tub?
  16. Do you like grand gestures?
  17. Do you forgive people easily?
  18. What’s the best relationship advice you would give your kids?
  19. What color do you think I look best in?
  20. Are you insecure about anything?

Simple Questions

  1. Do you like me as a friend or something more?
  2. Who are your family and friends?
  3. What’s your favorite animal?
  4. Where were you born?
  5. Where did you grow up?
  6. How did you perform in college?
  7. What’s something you can’t tolerate?
  8. What was your most memorable birthday?
  9. Do you have any questions for me?
  10. Have you ever lied to get what you want?

You may want to ask personal and deep questions to really get to know a guy and determine whether he would be a good match for you. Some girls like flirty and dirty questions to keep things sexy because all they’re looking for is a fling, while others need simple and unique ideas to start a conversation with a guy they have a crush on. What you talk about will depend on your relationship goals and personality as well as the guy and his interests.

While having great topics and cool stuff to talk about can be helpful, it’s important to consider context and timing. A random thought is different than an inappropriate question for the moment and you’ll want to pay attention to the guy’s reactions and responses. When talking to a new guy, you’ll need to begin slowly, cover the basics without resorting to small talk, and not interrogate him with several questions all at once. Good relationships grow naturally and with so many interesting things to talk about, starting a great conversation in person, over text or on the phone should be easy.

To inspire you with ideas, we’ve compiled a list of the best questions to ask a guy. From deep topics to funny stuff, explore the best things to ask a guy you like to get to know him and keep the conversation going.

Questions To Ask A Guy

Good Questions

If you want to avoid small talk and get to know your boy better, these good questions can help you discuss topics that are universally relatable. Whether you want to keep him engaged and interested or just need ideas that will naturally build rapport, there are many great questions to ask a guy that will bring you closer. When bringing up different topics, make sure you have the right timing and work these questions into the conversation naturally.

Good Questions To Ask A Guy

What’s your all-time favorite movie that you’ve watched many times?

It’s always endearing to know that a guy’s favorite movie is a veritable tearjerker. Whether he’s got a soft spot for the original “Home Alone” movie or prefers action-packed Marvel flicks, discussing his favorite movie certainly makes for interesting conversation.

What did you want your job to be when you were a kid?

Not everyone is cut out to be an astronaut or film star. Although there are plenty of normal jobs that kids grow out of, learning that he wanted to be a professional hot-dog eater is sure to give you two something to laugh about. If possible, ask why he gave up on these childhood career ambitions. It may teach you more about his practical approach to life.

Ask A Guy About His Future

If you could go on vacation anywhere in the world, where would you go?

Does he want to explore the Great Barrier Reef in Australia, or would he prefer an all-expenses-paid trip to Las Vegas? His bucket list spot not only gives you plenty of scope for vacation planning, but it should tell you what makes him feel alive.

What would you do if you won the lottery?

If your guy plans to blow his entire lottery winnings on gambling and booze, then he may not be the most fiscal individual around. However, if he has a decent financial plan for stretching his loot or hopes to give some of it back to his family, he’s likely a responsible and forward-thinking individual.

Best Things To Talk About With A Guy

What do you find most attractive about a woman?

If you’re at the flirting stage with a guy, you can subtly ask him what he finds most attractive about a woman. Depending on his answer, you can play up the features that he favors to get in his good books and capture his attention.

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.

Questions For Guys

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

Whether it’s the endless support or the reliable intimacy, what they value in a relationship is important to understand. Having frequent discussions about your expectations will keep your partnership healthy and thriving.

Would you wait for me to watch the next episode of a TV show we started together?

When you’re in a relationship, there is no greater sin than pressing play on the next episode without your significant other present. Although watching ahead isn’t a deal-breaker for most people, knowing that your guy will wait in suspense for you to settle in is heartwarming.

Casual Questions To Ask

What is your biggest pet peeve about dating?

If you feel comfortable enough, ask your guy about what he hates about the dating game. There are wonderful things that come with getting to know a potential partner, but if you both can skip the arbitrary rules and make dating a more pleasant experience, then you should!

What is your favorite compliment to receive?

If you can find out what makes your guy feel good about himself, you can pull out the perfect compliment when he needs it most.

Good Questions To Ask A Guy You Like

What do you think your best physical feature is?

If a man spends hours in the gym each week, he probably wants you to notice. Depending on his answer, you can subtly compliment your guy on his favorite physical feature when the mood strikes. If it’s appropriate, you may even want to lightly touch this area or bring attention to it when you’re flirting.

What would happen on a perfect date night?

Not only does this make for a great conversation booster for when you run out of topics, but it encourages you both to plan an incredible date that you’ll wholeheartedly enjoy. If he mentions something particularly corny, some light teasing wouldn’t go amiss!

First Date Questions To Ask A Guy

Should men and women have different roles in a relationship, or should it be based on individual strengths and weaknesses?

Relationships require clear boundaries and expectations. Therefore, you should take the opportunity to figure out your respective roles once you start dating. The last thing you’ll want is to be stuck in a role that you’re not comfortable with, so don’t be afraid to be assertive if you don’t agree with his take on your responsibilities.

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

Whether it was coaching him for an important class or giving him the perfect gift for his birthday, this is a conversation that will allow you to measure up. You don’t need to improve upon his amazing experience, but the gesture he discusses can tell you a lot about how others value him.

Cute Questions To Ask

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

A man loves to talk about his accomplishments, so be sure to give him space in a conversation to discuss the most impressive thing he’s ever done. Not only will this allow him to shine, but it will shed light on the kind of guy he is.

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

Perhaps he thinks your charity work reveals a lot about your generous nature, or your intense gym schedule is indicative of a driven personality. The answer to this question is likely to vary, so listen intently.

Revealing Questions To Ask A Man

What do you tell women about yourself to impress them?

We all have incredible stories that make us look amazing on paper. Although it’s unlikely that he’s saved someone from a burning building, hearing his most impressive story or anecdote is sure to leave you two with plenty to talk about.

What is one thing you never get bored of?

Is it long hikes during the summer or an intense session of video games? Something a man never gets bored of often speaks volumes about his hobbies and interests. If you can, suggest that you engage in one of these activities together. He’s sure to appreciate your willingness to be part of his world.

What To Ask A Boy

Would you ever change career paths or do you see yourself having your current job until retirement?

Not everyone is head over heels in love with their job. He may be happy with where he is, but if he isn’t, offer the support that will encourage him to move on and find something that he can’t wait to wake up for each morning.

What’s your favorite type of alcohol or cocktail?

The answer to this question will help you learn if he’s a classic beer drinker, enjoys Scotch whisky, or has a secret love for cocktails. Not only will knowing more about his favorite drink help you get inside his head, but it will make buying rounds so much easier.

Top 21 Questions To Ask A Guy

If you need things to talk about to ensure an intriguing and fresh conversation, these are some of the best questions to ask a guy that will keep the dialogue going. Some topics are appropriate for a first date or conversation online, while others can offer a starting point when talking to a friend who you might have feelings for. While you’ll need to choose which topics are appropriate for you, these questions will give you fun ideas.

What do you look for in a girl?

It may feel awkward to ask a guy what traits he looks for in a girl. However, knowing what he values will allow you to see if you align with what he envisages as his ideal partner. Whether he values personality or looks above all else, figuring his taste out from the start will let you know if a relationship is worth pursuing.

Top 21 Questions To Ask A Guy

If you love someone, do you wait for them to say it first or would you just tell them?

When you’re in a new relationship, waiting to hear those magical three words for the first time can be anxiety-inducing. Knowing where he stands with saying “I love you” should help to manage your expectations early in the relationship. Some guys simply don’t feel comfortable dropping that all-important phrase before their partner does, no matter how confident they may appear.

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

You’ll be able to figure out just how far you can push his folks with this leading question. If your crush was berated for staying out ten minutes past curfew when he was simply stuck in downtown traffic, then you’ll know you’re dealing with strict parents that you may need to handle with care.

Things To Ask A Guy

What is something everyone always gets wrong about you?

This question should gently nudge a guy into filling you in on personality traits that lie beneath the surface. Maybe he’s got an agitated resting face that leads people to believe he’s unfriendly, or perhaps people think he’s a happy-go-lucky guy when he’s an introvert. Whatever his answer, it should give you more information about the real him.

Who is your role model?

Most men will look up to those who have achieved greatness in one way or another. If he’s inspired by a celebrity’s philanthropic work, then you may have a charitable guy on your hands who wants to invest time into giving back.

Cool Questions For Guys

Why is your best friend your best friend?

A guy’s best friend is his right-hand man. Finding out more about the qualities that his best friend offers will turn you into that perfect shoulder to cry on during hard times. Most good relationships have strong friendship at their core, so try and engage with the qualities that he values in his closest friends for a connection that can weather any storm.

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

To get on his good side, make sure you find out what instantly turns a guy off. If you are trying to pursue a relationship with a man, you won’t get very far if you engage in behavior that he can’t stand! Any turn-offs that are intrinsic to your personality can’t be changed but if he hates when girls are on their phones during conversations, that can be easily remedied.

Questions To Ask A Guy You Like

What makes you smile even when you’ve had a bad day?

Lift his mood instantly by keeping the answer to this question in your back pocket. Maybe he loves long walks in the sunshine to boost his mood or loves to switch off with a trip to the movies. Whatever his answer is, it gives you great ammunition that will put a smile on his face when the time comes.

What’s something you’ve never told anyone else?

It can be tough getting guys to share secrets, but once they do you may well become their top confidante. Knowing his deepest secret is sure to bond you guys on a deeper level, regardless of how silly his answer may be.

Best Questions To Ask A Guy You Want To Get To Know

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.

What are three words you would use to describe yourself?

The three words game always produces interesting answers and should give you a decent idea of how a man views himself. If he describes himself as intelligent or funny, be sure to find ways to compliment him on these attributes down the line. He’s sure to enjoy the affirmation!

Questions To Ask Someone You Are Talking To

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

Although you need to be careful not to use this to level expectations on a guy, it can be a useful question to ask if you want to learn more about a man’s generosity and respect for women. If he went out of his way to make a woman happy in the past, he’s likely willing to do it again!

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.

Things To Talk About With A Guy

What is something you think everyone should experience at least once in their life?

Whether they feel that everyone should explore a certain country or jump out of a plane, what a guy considers an unmissable life experience gives you the perfect opportunity to plan an incredible and meaningful trip together.

What have you always imagined doing with a girlfriend that you’ve never done?

If you’ve recently gotten into a relationship with a guy, then you can one-up their previous partners by becoming the girlfriend they’ve always wanted. Have they always wanted to hang a lock at the Pont des Arts in Paris, or do they dream about a candlelit couples massage? Whatever his answer is, chat about accomplishing this together as soon as you can.

Good Questions To Ask A Guy To Get To Know Him

What were you like in school?

Were they the class clown or were they the classic, studious type? What someone was like at school can tell you a lot about their work ethic, but it also opens your conversation to hilarious childhood stories.

What’s the next goal, big or small, that you want to accomplish in life?

Goal setting is often the sign of a successful and driven individual. Not everyone has lofty ambitions and long-term goals, so don’t push this question too hard. However, learning that they want to live abroad or get that all-important promotion can reveal a lot about what they deem important both personally and professionally.

Great Topics To Discuss With A Guy

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.

Conversation Starters With A Guy

What do you expect from a relationship?

If your crush is looking to keep things casual and you’re looking to settle down, you may simply be incompatible. However, if your expectations align, you can work in tandem to become the power couple that all folks envy.

What are some non-negotiable boundaries you have?

Out of respect, you should never cross someone’s clear boundaries. Just as girls may be uncomfortable with their man frequenting strip clubs, he may hate that you still text your ex. If you two get your boundaries cleared up from the outset, you’re much less likely to experience arguments.

 

Interesting Questions

Interesting questions are a great way to show a guy that you’re fun and refreshing to talk to, which will make you more attractive to him. When you want to add spice and keep the conversation entertaining, ask a guy these cool questions to get him talking about his interests and passions.

Interesting Questions To Ask A Guy

What’s the most ridiculous talent you have?

Special talents are always attractive, but it’s the weird ones that can blow us away! It may not be a useful or overly impressive talent, but it’s an extra layer to his personality that you can uncover.

Which celebrity would you want to meet the most?

A guy’s answer to this question will link closely with his interests. Whether he’d like to trade jokes with Dave Chappelle or get workout advice from Dwayne Johnson, you’ll learn more about his priorities and the people he admires, helping you decide if he’s a compatible partner. In the meantime, it will be fun to talk to him about something he is passionate about.

What have you done that you’re most proud of?

Talking up a guy’s accomplishments is sure to make him feel incredible and should bond you two even further. When he’s feeling down, you can remind him of that time he nailed that big job interview or helped his closest friend in their time of need.

What’s something on your bucket list you really want to do soon?

It’s difficult to find time to accomplish our wildest dreams when we’re just trying to muddle through life. To give him a nudge, ask him what he’d like to tick off that all-important list soon. Give him a deadline and stick to it together!

If you could meet one dead celebrity, who would it be?

The celebrity that your guy chooses will tell you a lot about their passions and interests. History buffs may wish to learn more from famous figures, whereas struggling artists may seek words of wisdom from artists who defined a generation.

What was your favorite candy or treat as a kid?

Nostalgia is a powerful thing, so don’t be afraid to discuss your favorite sweet treats that rocked your world back in the day. If you remember popping candy and mysteriously flavored jellybeans, there’s a good chance he does too!

What is the coolest vacation you’ve ever taken?

Learning about your guy’s most unforgettable vacation will give you a great idea about how he likes to spend his leisure time. Be aware that what counts as cool to one guy may well be unappealing to another. Depending on his personality, be prepared for everything from a trip to Disney World to a train ride across continental Europe.

What’s your earliest childhood memory?

Our earliest memories can be fuzzy and unreliable, but some people have vivid recollections of their early days. If the memory stands out, it probably relates to either an incredibly positive or traumatic experience. Tread carefully here in case you hit a nerve.

What’s the worst and best thing about being a guy?

This will probably elicit some hilarious responses, so be prepared for some belly laughs. If he answers with something more meaningful or troubling, be open to his energy and offer something equally difficult about being a woman.

Would you rather find true love today or win the lottery next year?

There’s nothing wrong with being financially motivated, but there’s something beautiful about wanting love over money. If you’re on the hunt for a hopeless romantic, then a man’s answer to this question should help you figure out whether you’re dealing with one.

What is one thing you love about where you live?

Everyone has that tiny corner coffee shop that they adore. Find out about his favorite local spots and offer to check them out together when you’re next available.

Would you rather have another 10 years with your partner or a one-night stand with your celebrity crush?

It’s unlikely that any guy would say they’d trade you in for a celebrity, so keep this conversation lighthearted and fun! However, remember that celebrity hall passes exist for a reason!

What’s your kinkiest turn-on?

He may be very vanilla in the bedroom. However, if he’s not, then take the opportunity to ask about his kinkiest turn-on that will spice things up. Sexual compatibility is key for any good relationship, so don’t be afraid to push your conversations and find out what he likes.

What was your best drop-the-mic moment?

Is there a time when he called out bad behavior at work or stood up for a stranger at the local coffee shop? Whatever it is, he’s sure to be proud of his triumph over negativity.

If you had three wishes, what would they be?

Asking what someone would wish for if they could have anything in the world tells you a lot about their priorities. If he says he’d end world hunger, strive for peace, and give the final wish to his folks, you’ll know you have a stand-up guy on your hands.

What was your favorite cartoon as a kid?

Talking about your childhood memories is a great way to break the ice. Your nostalgic conversation should lead nicely into talking about your experiences growing up and how they shaped you as people.

Is there a song that always brings up old memories for you?

If a guy unashamedly listened to Carrie Underwood’s “Before He Cheats” after a bad breakup, then you can both laugh about this for days on end. However, as songs are a powerful way for us to connect to specific moments from the past, he may well have a song that speaks to his sensitive nature differently.

Where do you think the most romantic vacation would be?

Lying under the stars in Barbados or exploring the great lochs of Scotland might be your idea of romantic heaven but they may not be quite his style. To learn more about what your next vacation might hold, ask him for details on what he finds romantic and try and make it happen.

What’s the most dangerous experience you’ve ever had?

Although some dangerous experiences are entirely voluntary, some guys have had terrifying experiences that make for incredible stories. If he’s been faced with true danger, allow him to share his story.

Have you ever told a small lie that spiraled out of control?

White lies are a natural part of life, so even the most honest men have told them. Perhaps he called in sick at work for a baseball game or told his mom that he loved her gift and is now saddled with an ugly Christmas sweater every year. Whatever his answer, it’s sure to be insightful and amusing.

What long shot have you taken that really paid off?

Sometimes taking risks can reap massive rewards. Let him brag about the time he defied all odds to come out on top!

Funny Questions

Funny questions can break the ice and spark cool conversations that will make him laugh and stay engaged. These fun and playful topics will also allow him to relax, get more involved in the conversation, and open up to you. If you want to lower social anxiety and ensure a guy enjoys talking to you, these silly and happy questions to ask are a good bet.

Funny Questions To Ask A Guy

What is something you’ve never been good at doing?

Maybe he dreads public speaking or just can’t get his head around ballroom dancing. Whatever it is, his answer is sure to surprise you! After all, not many people actively advertise their weaknesses.

What’s the dumbest thing you’ve ever seen somebody do?

People are interesting creatures and he’s likely seen some strange behavior around town. Recount your stories and have a good laugh about the weird, wonderful, and stupid humans who walk the earth and make life fun and funny to live.

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

Not all dates are success stories. If you’re looking to liven up your dates together, ask about his weirdest experiences. It will also help you know what behaviors to avoid on your dates!

What’s your go-to move when flirting with a girl?

It’s useful to know how a man flirts as it allows you to gauge whether he’s putting the moves on you. If he mentions an ineffective move, don’t be afraid to playfully tease him about it.

What’s the worst pick-up line you’ve ever heard?

Ridiculous pick-up lines are always a great way to get a conversation started. Although they’re rarely effective, you two can take turns offering terrible pick-up lines until you both beg for mercy.

What’s the funniest thing that’s happened to you?

Nothing lightens the mood like a funny story. To get to know each other better, ask him to share the funniest thing that’s ever happened to him. There’s guaranteed to be an excellent story behind it, so listen up!

What was the weirdest punishment your parents gave you when you were growing up?

Whether strange punishments whipped him into shape or not, recounting them is sure to elicit some laughs!

What or who do you think you were in a past life?

If he’s into spirituality and reincarnation, then humor him by asking about his past life. You may just be able to connect the fascinating dots and become a believer yourself.

Who’s your favorite comedian?

Nothing raises your spirits like some good belly laughs. If you find out who his favorite comedian is, you can schedule comedy date nights and better understand his unique sense of humor.

Have you ever been asked to leave a public place?

Being kicked out of an establishment can be embarrassing and there’s usually a funny story that goes along with the event. Whether he was booted out for being too drunk or simply tried too hard to pet a stranger’s dog, this question is sure to give you a look at his wild side.

What is your best corny joke?

Let him embrace his goofy side by asking for his best corny joke. It’s unlikely to be funny, but you’ll probably be able to offer at least a polite laugh in response! When he’s done, feel free to share your own.

What’s the cheesiest line you’ve ever used that actually worked on a girl?

We’ve all heard the line about an angel falling from heaven and wondered if it’s ever been effective in the real world. Don’t be afraid to put him on the spot and ask which of his cheesy lines has had the most success.

What would you do during a zombie apocalypse?

Although it’s purely hypothetical, knowing how he’d respond to a fight or flight scenario is always useful information to have. This question can also be entertaining and fun because it allows you to be playful with creative scenarios and ideas.

What’s the worst thing you’ve done on a dare?

Truth or dare can lead to some messy outcomes, so don’t be afraid to cheekily ask just how far he’s gone in the name of the game. If he’s done something that’s bordering on illegal, be sure to keep it to yourself!

What’s your favorite curse word?

There are a plethora of fantastic curse words that are thrown around daily. Though it’s not recommended to scream your favorites out in public, having a quiet word about your most cathartic curse word can certainly break the ice.

Which direction do you hang toilet paper?

Perhaps he’s never thought much about it, but some guys are very particular about the face-down or face-up hanging methods. Learn his favorite direction and you’ll never be considered an unwelcome house guest.

If you could come back as anything in your next life, what would you choose?

Not everyone believes in reincarnation. Asking about what he’d love to be in another life is sure to prove fascinating. He may want to be free like the birds or try to improve upon his own life with an identical second chance.

If you were a girl for a day, what would you do?

The answer to this question may well get X-rated and can be a great intro into a dirty conversation. It’s always interesting to know what the opposite sex would choose to do if they switched bodies for the day. Whether your guy would focus on the physical aspects or try to get inside a woman’s mind will tell you about his priorities and thoughts.

What’s something you’re really bad at?

No matter how hard we try, some things just aren’t meant for us. Whether it’s juggling or basketball, finding out what a guy is bad at can humanize him.

Personal Questions

If you want to get to know a guy you like, you’ll need to ask him personal questions that scratch more than just the surface. When discussing personal stuff, you’ll need to work these ideas into a conversation naturally, ensuring that the time, place and mood are right. To be successful, you must read the room, set the stage, avoid suddenly changing topics and allow for a little back and forth while casually working your questions into the conversation.

Personal Questions To Ask A Guy

What did you notice about me first?

It may sound like you’re fishing for compliments but finding out what people first notice about you can be both interesting and affirming. Whether it’s your eyes, legs or sparkling personality, you’ll get an interesting look into how others perceive you.

How do you feel about PDA?

You don’t want to be planting kisses on a guy if he’s not comfortable with PDA. Before you start making out in public, check what he’s comfortable with. If in doubt, keep things private!

What’s your favorite childhood memory?

Find out more about his early life and how he grew up. His adorable stories of days gone by are sure to connect you on a deeper level and should give you further information about his family life.

What’s an embarrassing moment you had growing up?

No matter how awesome we were as kids, everyone has an embarrassing schoolyard story that they still cringe at.

What is one thing that always makes you angry?

Knowing what turns his pressure gauge from zero to a hundred is sure to come in useful when you’re trying to diffuse tension. Every relationship must deal with conflict at some point, so avoiding phrases or actions that make him angry will lead to shorter arguments with less fallout.

If you could re-do one moment in your life, what would it be?

Even the most successful people in the world have regrets. Finding out what he’d like to re-do from his past will reveal layers to his personality that you may not have seen at first glance. If possible, encourage him not to dwell on it too much as the experience shaped him into the wonderful man he is today.

Have you ever been betrayed by a friend?

Being betrayed by someone you hold dear feels like a knife in the gut. Although he may not be keen to discuss this too deeply, learning about his greatest betrayal can help you steer clear of making the same mistakes in the future.

Are you more into giving or receiving?

Depending on his love language, he may prefer to receive gifts than give them. However, some guys love showering girls with gifts. To keep your expectations in check, gently ask this question to see what you can expect down the line.

How much porn do you watch?

Porn can make or break a relationship depending on the parties involved. If his porn consumption is too intense for your liking, then be sure to lay down boundaries to avoid confrontation or mistrust as your romance progresses.

What do you worry about?

Knowing what keeps him awake at night will allow you to be his guiding light and voice of reason. Often, all someone needs is some encouragement to be able to tackle their biggest worries.

Who has completely lost your respect?

Whether it’s a celebrity or someone closer to him, knowing what causes someone to lose his respect is important. To avoid falling from his good graces, don’t mimic the actions of his top offender!

When do you know it’s time for a woman to meet your family?

Meeting the parents can be a nerve-wracking experience for any partner. Asking when he thinks it’s appropriate to meet the parents will help you manage your expectations and prepare adequately for when the time comes.

What’s the dirtiest thing you’ve tried during sex?

If you’re in a sexual relationship with a guy, then it’s well worth digging more deeply into his desires and past encounters. If he was grossed out by his dirtiest experience, be sure to leave it off your bedroom bucket list.

Are you still close to an ex-girlfriend?

Depending on your relationship history, you may or may not be comfortable with a man being in contact with his ex. If this is a hard boundary for you, either discuss it openly with your boyfriend or consider whether moving forward together is in your best interest.

Which of your physical features are you most proud of?

Knowing what a man loves about himself can help you out when he’s feeling down. Complimenting his best physical features will not only give him a much-needed boost but will help you know which areas to focus on during foreplay too.

Have you ever ghosted a girl and why?

In a world of dating apps and blind dates, it’s unsurprising that ghosting is relatively commonplace. Although this question may be awkward to ask, it’s worth knowing if there’s a chance that your dream man will suddenly disappear.

What’s something you’ve never told your family about?

A man who tells his family members every minute detail of his life may be prone to oversharing. You can use his answer to figure out what his boundaries are like and get some inside information too.

Have you ever dated a friend’s ex?

Although he may respond to this rather sheepishly, it’s always fun to tease a guy about dating his friend’s ex. Just be aware that this is usually against the unwritten guy code, so it may point to holes in his moral compass if he has done this.

What is something you took for granted in your last relationship?

To allow you to meet the one, every relationship must fall apart. To avoid experiencing the same frustrations as his ex, check in to see what he tends to take for granted in his partners.

Do you get offended often?

It’s difficult to have productive conversations with someone who’s offended by everything you say. To avoid treading on eggshells, it’s good to know how often your partner takes things to heart.

What comforts you the most?

Regardless of whether it’s warm hot cocoa or a Netflix marathon, finding out what comforts a guy will help you brighten up his dark days.

What was one time you really stepped out of your comfort zone?

Courage and risk-taking are attractive qualities in men, so discuss a time he decided to shoot his shot. You may just learn something new about how he got his current job, met his best friend, or decided to come up and talk to you!

What is your biggest guilty pleasure?

If he loves to dance around to Britney’s Greatest Hits on a Saturday night, then you should know about it from the outset. If you share a guilty pleasure, then it’s a great idea to indulge your obsession as a twosome.

What do you daydream about every time you’re bored?

Daydreams don’t necessarily reflect the inner workings of our minds, but they often nod to our goals, hopes, and dreams. If he can chat openly about his daydreams without embarrassment, you’ll know you’re one of his more trusted companions.

What’s the craziest thing you’ve ever done?

This doesn’t have to be relationship-related, it can be anything from sneaking out past curfew to stealing some bottles from a liquor store. This should let you know whether you’re dealing with a bad boy or a veritable good guy.

Deep Questions

Deep questions can help take your relationship to the next level and allow you to understand the heart and soul of the guy you’re interested in. These serious topics should be reserved for conversations with guys you actually like, may consider dating long-term or actual boyfriends. With the right environment and mood, these deep questions to ask will strengthen your connection.

Deep Questions To Ask A Guy

What’s your biggest fear?

The world can be a scary place, so why not learn more about what gives him the creeps? Use this as an opportunity to discuss your fears too. Perhaps you have more in common than you think.

Who do you admire most in life?

Whether it’s a close family member or a celebrity, the person he admires most in life is a name that you’ll want to remember.

What made you choose your career path?

Unless you’re dealing with a guy who works in the medical profession, it’s unlikely that he was settled on his career path early on. Many people choose careers that match their strongest traits, so this is a useful question to ask any high-flying guy.

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

He may not be able to cure world hunger but may feel attending protests and working hard on recycling is enough to make a marked difference.

What would you change about your family dynamic?

Discussing family dynamics can be tricky for those who aren’t part of a strong familial unit. Learning about what he’d like to change about his family will help you set your future for success.

What kind of father would you want to be?

If your man has expressed an interest in parenting, then throw this hypothetical question into the ring. Would he be lenient or strict? It’s worth knowing who’s going to be playing good cop and bad cop down the line!

Do you believe in a higher power?

If he’s an incredibly spiritual guy, then you’ll want to respect that from the outset. Should you disagree strongly with his beliefs, you may not be compatible.

Are you more of a free spirit or do you appreciate a strict schedule?

Although it may come as a surprise, some of the best relationships work well when the partners are total opposites. Even if you roll with the punches and he sticks rigidly to his day planner, you may well balance each other out perfectly.

If you could change the past, what would you do?

Would he choose to assassinate Hitler or save Abraham Lincoln from his fate? If he answers this on a more personal level, feel free to dig more deeply for answers. He may have lived through a trauma that he’d rather forget about.

What was the last thing that made you cry?

Some men are afraid to show their sensitive side, but most women appreciate a man who isn’t afraid to cry. Whether it was a touching movie or a traumatic event that set him off, be sure to let him know that you value his emotional response.

What motivates you in life?

Motivation is an important tool that will drive a man to be successful. You’ll want to learn what drives him to be better, what he is working to achieve in his life, and the impact he wants to make on the world. From money to helping people, understanding the things that motivate this guy will help you appreciate where he wants to go in life.

Has anyone ever broken your heart?

All breakups hurt, but there may be a particular ex that broke his heart into a million pieces. If he’s been unlucky in love, work to rebuild his trust with plenty of support and positive affirmations.

Have you ever lost someone close to you?

This is always a sensitive topic of conversation, so it’s best to approach this with a guy you’re comfortable around. If he opens up to you, be supportive, understanding and offer him room to discuss the person he lost should he wish to.

If you knew the world was going to end in a week, what would you do?

This interesting question will tell you about a guy’s priorities and bucket list. If he chooses to visit every person he holds dear, then you’re probably dealing with a sensitive, loving man. If he’d rather visit his ultimate vacation spot, he’s more likely to value culture and experience.

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

Not everyone leaves behind an incredible legacy, but that doesn’t mean he doesn’t want to be remembered after he dies. Some guys just want to have an amazing family, be part of a community, do good in the world and have a happy life while others would rather be known for their professional accomplishments. The ideal guy will discuss a work-life balance that ensures his family comes before his career ambitions.

How would you describe me to someone who doesn’t know me?

Do you ever wonder how you come across to others? If so, ask what physical features and personality traits best describe you. It just may surprise you to know that you have twinkling eyes and a killer laugh.

How do you define love?

He may not see love in the same way you do, so be ready to open your heart and mind to a new perspective.

What motivates you in life?

Passion and motivation are incredibly attractive and it’s always worth asking about what makes someone tick. If you have similar motivations, then you’re in a great position to move forward together.

What’s your worst habit and how are you working on changing it?

Everyone has bad habits but not having the foresight to work on them can be a dealbreaker for many. Asking about his bad habits and sharing your own will help you encourage each other to better yourselves one step at a time.

What event has had the most impact on you?

Not only will this tell you more about his past, but it will give you a good look into what shaped him into the man he is today.

How do you know when you’re in love?

Everyone falls in love differently so listen carefully to his answer so that you can sense when he’s starting to fall hard.

Random Questions

To keep it spicy and intriguing, you can ask these random questions that apply to any guy. If there’s ever a lull in the conversation or you just need something light to talk about, these random thoughts might offer the perfect solution.

Random Questions To Ask A Guy

If you could marry one celebrity, who would it be?

Being able to tease a guy about his celebrity crush is always fun. Whoever it is, be sure to pick them out in movies and commercials whenever they appear. He may seem irritated at first but remind him it’s all in jest!

What’s something on your bucket list you think you’ll never actually do?

Despite being a combination of things that we wish to accomplish before we die, some bucket list items just aren’t plausible. If you feel it can be done, encourage him to keep pushing to make it happen.

What do you always lie about on your resume?

We all tweak our resumes to land dream jobs. Perhaps he’s noted that he has acrobatic skills or slightly modified his last job title. As long as he’s not massively altering his employment history, you can both have a good laugh about this one.

Which show could you binge-watch more than once?

If he has a comfort show, then you should certainly consider catching up on it. He’ll appreciate the effort and enjoy discussing your thoughts on every aspect of the show.

Would you rather go camping or clubbing?

Some guys love the intense atmosphere of a club, whereas others love the wistful, serene quiet of the Great Outdoors. You will want to be on the same page with this one, as there’s nothing worse than being dragged to a bustling club when you’re not feeling it.

Have you ever bullied someone or has someone bullied you before?

Not all guys will give an honest answer to this but knowing about their experience with bullying can tell you a lot about why they’ve grown into the person they are today. Previously bullied individuals can be hardy and defensive, so knowing more about their past can help you understand a man’s reaction to certain situations.

If you could see any artist or band, alive or dead, in concert, who would it be?

Does he want to catch Queen in their prime or would he unashamedly love to watch an Ariana Grande concert? As music is so personal, this will give you an amazing look into what he loves to rock out to.

How much time do you spend getting ready in the morning?

If you’re someone who needs their time in the bathroom, then you’ll want to make sure your prospective boyfriend isn’t going to monopolizing the bathroom. In addition to being irritating, too much grooming time could point to him being high maintenance.

Where is a place you never want to visit?

There’s no point wasting time discussing your dream vacation with a guy if he would never visit it in a million years. If you’re not overly attached to a place, you can make a joint decision to cross his least favorite destination off your list of locations to visit.

Are you happy with your life?

Tread carefully when you ask this question, as it can quickly become incredibly introspective. If you’ve noticed a man being withdrawn and quiet, offer to help him get to a better place in life. If he’s completely happy, then be sure to take notes!

Did you ever get spanked as a kid?

Knowing whether a man got spanked as a kid may reveal a lot about his guarded personality and aversion to physical touch. Spanking isn’t always a sign of poor parenting but it’s worth asking whether he feels it’s an appropriate disciplinary measure for kids if you fundamentally disagree with it.

If you were a dictator, what laws would you make?

Not many of us can make lasting changes in the world, so it’s always interesting to know how a man would respond to having ultimate power over people. Would he use his influence for good or choose to be controlling and overbearing?

What’s your favorite store?

If he loves a bit of retail therapy, then it’s a great idea to find out what his favorite store is. Not only will this prove useful for gift ideas down the line, but you two can easily head on a playful shopping date afterward.

Do you trust people easily?

It’s useful to know how hard you’ll have to work to break down his walls. As a rule, some people trust more easily than others. Therefore, prepare to be patient with him if he admits that it may take him time to trust you.

What did you think was silly until you tried it?

Whether it’s karaoke or electric scooters, finding out what changed a guy’s mind about something is always interesting. If you’re unsure about the activity yourself, why not let him inspire you and try it out together? You may just find a new hobby!

Weird Questions

For interesting and unique topic ideas that work, you can try to ask these weird questions. Most guys don’t like talking about the same things over and over again. When you’re feeling stuck, use these unusual conversation starters and topics to get him going.

Weird Questions To Ask A Guy

What fun activity from your childhood has been completely ruined for kids today?

With each decade comes new ways to play. However, not every new game or activity beats its predecessor. Find out what he thinks has been ruined for kids today and spend time reminiscing over the good old days!

What game do you absolutely dominate when playing?

Allow him to show off his skills by discussing his awesome game tactics. Regardless of whether he excels at board games or video games, he’s sure to teach you a thing or two about how to dominate the competition.

What’s the most interesting dream you’ve ever had?

Dreams are often a reflection of our subconscious mind and can reveal a lot about our hopes and dreams. Although they’re not always meaningful, finding out about his most interesting dream may lead to a discussion about his deeper, more hidden desires.

What did you usually do at recess when you were in elementary school?

How your guy spent his time at school can tell you about his interests, personality, and social presence. If he was shy and anxious but is now bold and adventurous, ask him how he transformed. Some guys may have been outgoing kids until a traumatic event changed their lives.

What is the ugliest thing you own but still love?

Sentimental items don’t have to be beautiful to be loved. It’s bound to endear you to him if you learn that he still sleeps with a teddy bear that he received when he was born. It may only have one eye and look ragged, but that bear is a sign that he values sentimentality and meaningful gifts.

Where do you like to sit on a plane?

Although we’d all like to sit in First Class, this is a pipe dream for most. However, that doesn’t mean that you can’t find out about your partner’s seat preference! If you insist on sitting by the window, then you’ll pair excellently with a dedicated aisle or middle-seat lover.

Where would you like to retire?

There are so many options for retirement, so it’s always good to ask how they’d like to spend their twilight years. Perhaps they’d like to live by the sea or live out their days abroad. If you have similar views, your relationship likely has phenomenal staying power.

Where is your safe place?

When the world gets to be too much, it’s great to have a haven to escape to. He may not share his answer with you if he’s a private person. However, if he does, you’ll know that he trusts you with both his privacy and safety.

What board game always ends badly?

Although game nights don’t always end up with flipping the board in frustration, some games just bring out the worst in people. Does his family get way too intense with their property empire in Monopoly or get aggressive with Scrabble? Whatever his answer, be sure to remove it from your list of board game options to play together.

Do you have a restaurant horror story?

Restaurant horror stories always feel terrible at the time but are hilarious in hindsight. Whether he reveals that his card was repeatedly declined on a first date, or he had a waitress who was slightly too friendly, you can swap stories until you’re crying with laughter.

What is the most boring activity imaginable?

Everyone has different tastes, so it’s worth figuring out whether your love interest thinks your favorite hobby is an utter waste of time. If you both agree on a boring activity, have some fun ripping it to shreds. Keep it playful, of course!

What’s something about you that people don’t usually appreciate as much as they should?

Gratitude is a funny thing and many of us don’t appreciate how lucky we are. To get your guy’s perspective on the world, why not ask him this fascinating question. It’s likely to give you some useful information on how he views simple pleasures and his current position in life.

What’s your favorite kid’s cereal?

Something is comforting about eating a bowl of Captain Crunch on a lazy Sunday. To bring back fond memories of childhood, discuss what cereals used to get you two out of bed in the morning!

What is the most useful thing your mom or dad has taught you?

Advice passed down from mom and dad is often the most meaningful. If he has staunch family values or holds his parents in high regard, then this may give you a great insight into his approach to parenting and kids too.

What fact do you wish you had never learned?

Whether it’s a gross fact or a traumatic one, his answer to this question is likely to catch you off guard! If you have any major triggers or fears, be sure to warn him of them before he answers. The last thing you’ll want is to accidentally relive something from your past against your will.

Flirty Questions

When it comes to opening up and having freaky conversations, it can be a challenge choosing the right flirty questions to ask. Whether you’re sexting him or having a nsfw chat, these juicy topics will keep him engaged and begging you to keep talking.

Flirty Questions To Ask A Guy

  1. Do you prefer making out or cuddling?
  2. What’s your favorite sex position?
  3. Do you think about me when we are not together?
  4. What is your most embarrassing sex memory?
  5. What is your idea of foreplay?
  6. Have you ever had a dream about me?
  7. Who is your dream girl, if you couldn’t have me?
  8. How important do you think sex is in a relationship?
  9. What is the difference to you between sex and making love?
  10. What do you wear to bed?
  11. Are you shy in the bedroom?
  12. What physical features are you most attracted to?
  13. Have you ever wanted to tear my clothes off?
  14. Which one of my outfits turns you on the most?
  15. How many girls have you been with, before me?
  16. Have you ever had a one night stand?
  17. What do you want me to be wearing right now?
  18. Do you prefer to give or receive?
  19. What is your opinion on a girl making the first move?
  20. Would you ever shower with me?
  21. What part of my body would you want me to tattoo?

Sexual Questions

When it comes to naughty topic ideas that will blow his mind, these dirty questions to ask will turn him on instantly. Sexual questions are a great way to take your conversation to the next level and show that you’re really into a guy. While someone might get nervous talking about freaky stuff, you should know that almost all guys welcome these juicy bold subjects and love playing sexual games. If you’re planning on approaching these topics, make sure you know how you feel about him before moving forward.

Sexual Questions To Ask A Guy

  1. What’s your favorite thing about sex?
  2. What was your first sexual experience like?
  3. What body part do you like me to touch the most?
  4. Do you like when a girl gets on top?
  5. What kind of porn do you watch?
  6. What’s an act you’ve never done, but want to try?
  7. Do you like to go down on a girl?
  8. Would it turn you on to watch porn together?
  9. What’s your biggest fantasy?
  10. Do you like a screamer or do you like it quiet?
  11. How often do you masturbate?
  12. What do you enjoy most when I go down on you?
  13. How would you feel about a threesome?
  14. What sort of role play would turn you on most?
  15. What dirty words arouse you the most?
  16. Do you prefer to be dominant or submissive?
  17. What are your thoughts on anal play?
  18. What does consent mean and look like to you?
  19. What’s the one thing I can do right now to drive you wild?
  20. Do you have any fears or concerns when it comes to sex?

Conversation Starters With A Guy

Whether you’re going on a first date or just need a few ice breakers to text him, these conversation starters can be used with a guy to provoke banter and prevent awkward silences. Open-ended questions and fun topics can get him talking about the things he enjoys in his personal and professional life, helping you learn more about him without being too direct. Make sure to listen intently for details and clues that will allow you to naturally follow up with his answers and keep the conversation going all night, creating a great first impression.

Best Conversation Starters With A Guy

  1. What’s your story?
  2. What’s your favorite thing to do with your friends?
  3. Have you been working on anything exciting lately?
  4. What do you do to relieve stress?
  5. What made you smile today?
  6. How did you meet the host?
  7. What do you have planned this weekend?
  8. Do you have any personal passion projects?
  9. How would you describe yourself in three words?
  10. What did you want to be when you were younger?
  11. What do you bring with you everywhere and anywhere you go?
  12. What’s the most interesting thing you’ve read recently?
  13. What are your favorite restaurants around here?
  14. Where do you see this field going in the future?
  15. What’s the most important thing I should know about you?
  16. What is your guilty pleasure?
  17. What do you think is the best show on Netflix right now?
  18. Have you been on any interesting trips lately?
  19. What’s your coolest talent?
  20. What is the most rewarding part of your career?
  21. What did you do for your last birthday?

Questions To Ask A Guy To Get To Know Him

Asking the right questions can help you get to know a guy. While some guys don’t open up easily, others are talkative and extroverted, and may express interest early on. If you need help starting a conversation, these are great questions you can ask to get to know him.

Questions To Ask A Guy To Get To Know Him

  1. What’s your family like?
  2. What’s the scariest thing you’ve ever done?
  3. What would you say is your life philosophy?
  4. Would you describe yourself as more of an introvert or an extrovert?
  5. What question do you always ask women on a first date?
  6. What’s your dream car?
  7. Would you rather have universal respect or unlimited power?
  8. What’s your favorite song?
  9. If you could have any superpower, what would it be?
  10. What’s the best gift you’ve ever received?
  11. What’s your favorite cuisine and food?
  12. What do you enjoy most about your job?
  13. What’s the funniest joke you’ve ever heard?
  14. What’s your favorite time of the year?
  15. What makes you happy?
  16. What’s the stupidest thing you and your friends have ever done?
  17. What’s the hardest thing you’ve ever had to do?
  18. If you could change anything about yourself, what would it be?
  19. What’s your favorite college memory?
  20. What’s something you could not live without?
  21. Do you believe in love at first sight?
  22. What’s your go-to phrase?
  23. What’s your favorite curse word or insult?
  24. What did you spend your allowance on growing up?
  25. What’s the biggest life lesson you’ve learned and would like to share with your kids one day?

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