75 Revealing Questions to Ask a Guy You Like & Read Him Like a Book

He’s cute, funny, and smart. But do you really know him? Is he right for you? Try these questions to ask a guy you like to know everything about him!

Questions to Ask a Guy You Like

We’ve all liked guys we barely know. Whether he is cute, smart, or just checks all your boxes, there are some things you probably want to find out before trying to take things further. Maybe you just met, maybe you work together, or maybe you’ve been dating a while, no matter what the situation, the answers to these questions to ask a guy you like WILL help you to find out if he’s right for you.

These questions will not only give you a better sense of who he is, but help him know about you too. And most importantly, you will also get to find out some important facts about him while he learns about what is important to you. 

These questions to ask a guy you like will help you figure out what you have in common, if you wants the same things in the future, if you’re compatible, and more. And all of them, just by using the right kind of harmless and easy questions no one would think twice about answering.

You can even ask these questions to your boyfriend or someone you’re getting serious with, in fact, I recommend it. It is never too late to find out more about a guy you like. [Read: 22 early warning signs of a bad boyfriend you MUST know]

Some of these questions are simple and fun, and will give you an introduction and break the ice, while others are deeper and more personal for when you’re really considering a future with him.

The big list of 75 perfect questions to ask a guy you like 

When you want to get him to like you or know if you should continue to invest your time and heart in him, here are the best questions to ask a guy you like, featuring everything from flirtatious wonderings to deep insightful queries.

[Read: How to show a guy you like him, and still be a tease]

#1 Are you available? It is pretty clear why this is important. If you like a guy that is in a monogamous relationship, things won’t work out, so it is best to know now.

#2 Are you free this weekend? Ask him out if he is free. The best way to get to know him and have a chance to ask these questions is on a date. This way you can share undivided attention and really learn more about him. [Read: How to subtly ask a guy out over text and get the answer you want]

#3 What did you get up to over the break? Ask him what he did over the holiday break, the weekend, or on his vacation. This will help you learn about what he does with his time off and what you may do together if you were to date.

#4 What shows are you bingeing? I know TV isn’t that important but sharing common ground by bonding over a series can help things flow more smoothly.

#5 What’s your favorite streaming app? The same goes for apps and other entertainment. Talking about something a bit more light can break the ice and let you get into deeper topics that we’ll get to later. 

#6 Do you have any pets? Pets are so important. They are family so it is good to know if they have that soft spot for animals. If they are allergic or don’t like cats and you have two, things may not work. [Read: Adopting a pet? The true signs both of you are ready for a pet together]

#7 Where’s your favorite place to travel? For those with the travel bug, this is a great question to ask a guy you’re interested in. Do you both enjoy relaxing on a beach or doing touristy things or a bit of both? Does he like to explore places that are underrated or well-known landmarks?

#8 What are you most passionate about? If you’re looking for exciting questions to ask a guy you like, this this, ask him about his passions and you will see another side to him! When people talk about their greatest passions, they light up, they get excited, and seeing that is so important. It shows he is dedicated and driven.

#9 Do you like your job? This can tell you a lot about a guy. If he loves his job, he makes his happiness a priority. Or if he hates it, he may be disciplined and willing to climb the ladder or he puts money ahead of his joy. 

#10 Are you close with your family? This is important to many people. Is he close with this siblings or parents? Does he see them often? Does he prefer his chosen family to his given one? How have your family lives been similar or different? What can you connect on?

#11 What show can you watch over and over? This question to ask a guy you like usually tells you a lot about someone’s sense of humor which makes a big impact on how you will get along. Do they prefer Seinfeld or Friends? Maybe they are more into New Girl or Schitt’s Creek? Or perhaps they like something a bit more serious or dramatic?

#12 What do you do in your free time? Free time is the time you would potentially spend together, so knowing how he fills that time is important. If he likes to lounge around and watch TV while you’re super active, you may be too different or perhaps you could bring each other out of your comfort zones. [Read: 20 positive personality traits that can change your life forever]

#13 What are your dealbreakers in dating? I always think these are good to get out of the way now. If he doesn’t want to date a smoker and you’re a smoker, it probably won’t work out so neither of you should waste your time. [Read: The 25 most common dating deal breakers almost all women agree on]

#14 Do you have a secret talent or party trick? This is always fun to find out and can be a cute memory to share if it does work out down the road.

#15 If money wasn’t a factor, what would you be doing? I personally love this question to ask a guy you like. Although it may not be realistic or practical, it tells you a lot about someone. Would they be doing what they’re doing now? Would they go on a permanent vacation? Would they volunteer?

#16 What is your biggest pet peeve? This could be anything from racism to not put the shopping carts back, and it can tell you a lot about what people let get to them.

#17 How did you meet your best friend? This is almost always a good story. And hearing the guy you like, talking about someone who is so important to him will show you how much he cares about his friends. 

#18 What is something unexpected about you? This question is something that not only shows something you probably didn’t know about the guy you like but it also clues you into what he finds unexpected about himself.

#19 Are you more into maths and sciences or the arts? This can really give you a glimpse into his interests and mindset. If you are more creative and artsy while he is more clinical, that can give you a clue into your compatibility.

#20 Do you have a favorite quote? Not everyone does, but if he does, it is likely something he lives by which could let you know his morals and goals in life. [Read: 19 less-popular life quotes that’ll motivate you to live a better life]

#21 What would you do if you have 24 hours to live? This question can seem a little morbid but can also be very telling. Would he go see the most beautiful places on earth or hang out at home with his family? What would you do?

#22 What are you most proud of yourself for? I love this question because you get to see his confidence shine through. Some people, especially those who are shy, have a hard time patting themselves on the back but this question lets them do so.

#23 What is your favorite book and movie? Depending on if you are more of a movie or book person, this will let you know their tastes.

#24 What was your childhood like? This is one of those questions to ask a guy you like that’ll reveal his outlook towards life as a grown-up. Did he grow up with money or more humble? Were his parents together? Did his grandparents raise him? All those shows what he’s been through in his life and handled as a kid. [Read: The child of a narcissist and 16 lasting effects that will affect others in their life]

#25 Who has impacted your life the most? Is it someone he aspires to be like in business or his father or brother? What does that say about him? 

#26 Who are you closest to in your life? Knowing what his personal life is like can tell you how you click on that level. Is he super close with his parents or his best friend or his roommate? Does he have a ton of friends he’s close to?

#27 Do you believe in marriage? Is that something you want? This is one of those questions to ask a guy you like, that cannot be ignored. If you like this guy and are looking for a serious relationship, knowing his stance on a potential future is important. If he never wants to get married and you do, it’s going to be a very big issue some day in the near future.

#28 Who do you miss the most? His grandma? His childhood friend? His mom who lives across the country? Let him share that bond with you. Connecting with you over something so serious will bring you closer.

#29 What celebrity death impacted you the most? Was it Robin Williams who made him laugh as a kid, or Chadwick Boseman who made him feel seen in pop culture? Or was it someone else? 

#30 Do you have any regrets? It is nice to say you live your life with no regrets, but most people do have something they would have done differently. For him, is that something in his professional or personal life? [Read: 5 life altering lessons you can learn from regret]

#31 Have you ever been in love? If he shares this with you, he is being vulnerable. Maybe he’s been in love or thought he was, but after some time realized he wasn’t. His ability to think about that time and open up to you says he feels comfortable sharing with you.

#32 How do you deal with stress? This is important to your possible future. Will he shut down when he’s going through a hard time or will he open up and vent? Will he want advice and help or just to get it out? 

#33 Do you get jealous easily? Whether you’ve dealt with a jealous guy in your past before or not, I’m sure you know how that can go. It can be very controlling. Is he aware of this? Is he working on it? Is he secure in himself? [Read: How to tell if a guy is jealous – 25 hints he just can’t hide]

#34 Have you struggled with a mental illness? This is an important question whether you have struggled yourself or not. Are you capable of the patience needed to handle anxiety or depression from your partner? Will you be able to bond over shared experiences? Can you be there for each other?

#35 What’s on your bucket list? What is important to him that he wants to do in his life? Does he want to foster dogs? Does he want to visit all the continents? Does he want to make a million dollars in one year? Do you agree that these things are important? [Read: Couples bucket list and 20 things all couples must try to do]

#36 Do you find it difficult to trust people? This can tell you if you need to be patient with him or if you can both jump into something. Does he have trust issues from his childhood or a past relationship?

#37 What are your opinions on social media? Social media is like a lifestyle to some people. It can really eat away at a relationship. If he is very private and you love to share your daily life with thousands online, it can cause a rift. 

#38 Do you believe men and women should be treated equally? If he doesn’t say yes, you know what to do.

#39 What charities, organizations, or movements do you support? Do your opinions and passions align here? Would you go to the same protests together and volunteer together, or do you care about different causes or even care about opposing causes?

#40 Are you competitive? This question to ask a guy you like probably isn’t a deal-breaker, but can be intense for some people. If you are laid back and they are intense about winning, it could cause issues but if you both meet in the middle, that difference can be balancing.

#41 Do you follow any religion? If you share a religion, it is something you can bond over and if you have differing beliefs, it can be something you learn about each other. 

#42 Have you ever been heartbroken? If he has been through heartbreak, he may be more sensitive to your feelings or more slow-moving. This can help you understand where he’s coming from. [Read: 60 must-ask get to know you questions for a new romance]

#43 What are your political affiliations, if any? Politics can be an iffy subject for couples and if those positions matter to you, differing opinions here can be a deal-breaker. 

#44 Do you trust the government? I don’t want to get too into this, but with all the theories and conspiracies going around lately, it is important to know if you could be dating someone who lives in a different reality to you.

#45 Where do you see yourself in 5 years? or 10 years? This is a pretty basic question to ask a guy you like, but it says a lot about what you and he want. Do you both want kids and a family and to own a home or does one of you want to travel or drive cross-country in a converted van?

#46 Have you ever cheated on someone?  For those with trust issues, finding out someone cheated before could be enough to turn them off. But if he owns up to it and takes responsibility, you might take that as a sign of growth and maturity. [Confession: I cheated on my boyfriend with his friend and feel way, way better]

#47 Do you want to have kids? This is such a big topic and it matters a lot to your future. A lot of couples don’t talk about this until they’re already engaged or married. Sharing your feelings on this sooner rather than later is always a good idea.

#48 Would you adopt or foster? To take the topic of kids even further, knowing whether this guy would be open to adoption or fostering is important. Not everyone can have kids biologically and others would prefer not to. Knowing where he stands now can really make things easier later.

#49 What is your favorite board game? Will you crush him in Monopoly or Scrabble?

#50 Are you a feminist? If he says no, he probably doesn’t view you as an equal, so you can do with that what you wish.

#51 Do you recyclable, use reusable bottles, and care about the environment? If you take the environmental crisis in the world seriously and he tosses plastic bottles in the trash, that could be a small pet peeve that slowly drives you insane.

#52 What do you do when the power goes out? I love this question to ask a guy you like because it takes away phones, internet, TV and leaves you with old-fashioned bonding. Would you two play cards, eat all the food that might go bad, or just lounge around? [Read: What to do when you’re bored at home with nothing to do]

#53 Do you enjoy being single? Even if he says yes to this, it doesn’t mean he doesn’t want to date you, but it does let you know if he can keep himself company. 

#54 What is the longest relationship you’ve ever had? If he has never dated anyone for over 6 months, maybe he isn’t ready for something you’re ready for, or maybe he is fresh out of a seriously long relationship.

#55 If you had the chance, would you try again with an ex? This can be a hard one to hear the answer to, but it can be vital to whether or not you want to move forward with your feelings. [Read: 13 secret clues your boyfriend is definitely not over his ex yet]

#56 What makes you sad? This tells you what is important to him. Does his dog whining for treats make him sad or does the news make him sad? Or both?

#57 What is your favorite childhood memory? This is a fun question to ask a guy you like, that tells you something about his life before you and clues you into what sort of memories stay with him.

#58 Do you hold grudges? Is he quick to forgive if you mess up or does he hold onto his anger? Why does he hold grudges? 

#59 Have you ever been in a physical fight? Is he against violence? What was the fight about? 

#60 Do you practice monogamy? This is also important. If you are into having an open relationship, this could be a no-no for you and vice versa. If you two aren’t on the same page with what you would potentially want together, it probably won’t work. [Read: Is monogamy for you? How to know your needs and what works for you]

#61 What’s your favorite thing to cook? Not only will this let you know his cooking skills, but maybe his diet as well. Is he a meat and potatoes guy or is he vegan?

#62 Do you prefer the city or the country? Would he love to live in the center of NYC or does he prefer a rural area? What about you?

#63 Are you a morning person? This question could be a long way off, but it could give you some insight into your life together.

#64 Do you believe in ghosts? Is he spiritual? Maybe he is very skeptical about ghosts, psychics, and the paranormal while you believe in it? 

#65 What is the first thing you noticed about me? This can let you know how he sees you and what is important to him upon meeting someone new. [Read: 25 things guys find sexy and very attractive about a girl they see]

#66 Who do you look up to the most?  Does he look up to Michael Jordan, Barack Obama, or Oprah? Why does this person inspire him?

#67 What is your favorite series, saga, or fandom? Is he obsessed with Star Wars or Lord of the Rings? Maybe he loves Harry Potter or is super into the MCU. This can help you click on a more lighthearted level.

#68 What scares you the most? Is he afraid of climate change or the government or war? Is he worried about his future? Is he scared of losing his parents?

#69 Do you prefer summer or winter? I know this can seem like a simple question to ask a guy you like, but it can impact a relationship more than you know. Will you always fight over where to vacation or even where to live based on the weather?

#70 Would you travel to space given the opportunity? This is quite the conversation starter.

#71 Do you enjoy long car rides? Will you be going on any road trips or flying two states over? [Read: 20 fun, unique things to do on a car ride to make it memorable]

#72 What languages do you speak? I love this question because it doesn’t only tell you how diverse or educated someone is, but it also shows their history. Did they live in France for a while? Were they born in Mexico? Did they learn sign language because a family member is deaf?

#73 How would you describe a healthy romantic relationship? Are you on the same page? Do they want something simple and loving and comfortable or something passionate and wild? [Read: What does a healthy romantic relationship look like? Your guide to building the perfect one]

#74 Do you consider yourself to be stubborn or open-minded? Depending on where you fall on this spectrum, it could make a big difference where they do. If you are both stubborn and unwilling to bend on certain subjects, it could create a big mess.

#75 Do you like me? This is probably the most important question to ask a guy you like. If he doesn’t like you back, most of these other questions won’t really matter. But, if he does, you can move forward and get to know each other and hopefully become a great couple.

With this, remember that these are not meant to be rattled off in a list. You can’t just walk up to the guy you like and ask him these 75 questions. 

Take your time and enjoy getting to know him. These shouldn’t be checked off like a list but asked because you are genuinely interested in the responses and want to share your answers with him as well. 

Using just some of these questions to ask a guy you like will help you find out if he is really the right one for you. Try it, you’ll be surprised just how revealing and insightful it can be in no time!

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Samantha Ann
My name is Samantha Ann. I am 28 years old. It was always my dream to become an advice columnist, so after years of off and online dating and eventually finding...