108 Casual-Yet-Deep Questions to Ask a Guy to Get to Know Him in Minutes!

You really like him a lot. But how well do you really know him? Is he a good match for you? Try these questions to ask a guy you like and find out!

Questions to Ask a Guy to Get to Know Him

Maybe you just met, maybe you work together, or maybe you’ve been dating for a while. Regardless of 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.

Let’s be real, 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 more about before trying to take things further. 

These questions will not only give you a better sense of who he is but help learn more about know about you too. [Read: 71 friendly and funny questions to get to know someone better in a happy way]

These questions to ask a guy you like will help you figure out what you have in common, if you want the same things in the future, whether you’re compatible, and so much more. All just by asking 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, we 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]

How to know if you’re asking the right questions 

While getting to know a guy you like is always exciting and fun, it can also be a bit nerve-wracking too. [Read: 41 casual conversation starters to use with a guy to get him talking]

Since you have a crush on him, your emotions are running high and you might have some anxiety that you’re asking the wrong questions.

But just calm down. There really are no “right” or “wrong” questions. As we said in the last section, just “read the room” – meaning him. If you just started talking to him, then choose light questions like “what’s your favorite movie?”

On the other hand, if you have known him for a while, then you can go a little deeper with your questions. [Read: 62 flirty topics and things to talk about with a guy to keep him interested]

You might want to try ones like “what’s your favorite childhood memory” or “where do you see yourself in five years?”

And finally, if you are already romantically involved or dating, then it’s fair to ask him questions that assess your compatibility.

Questions about his political or religious beliefs would be appropriate because if the two of you are wildly different, it might not work out so well. [Read: 32 flirty and deep would you rather questions for couples to connect better]

Just remember to be yourself. Ask the questions that seem appropriate given all the factors involved, and you’ll do just fine.

The big list of 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? 

If it isn’t pretty clear why this is so important, then we don’t know what to say. 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? 

There’s nothing men love more than a woman who knows what she wants, so straight up 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 your 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? 

If you’re talking to a guy just after the summer or the festive season, then 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? 

Sure, 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 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 our furry family, so it is good to know if they have a soft spot for animals. 

If they are allergic or don’t like cats and you have two, things may not work, so it’s better that you know sooner rather than later. [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? This is a really good question to ask because no one likes to travel alone every time!

8. What are you most passionate about? 

If you’re looking for exciting questions to ask a guy you like, then ask him about his passions and you will see another side to him! [Read: 48 real secrets to change your life and find the right path when you’re lost]

When people talk about their greatest passions, they light up, they get excited, and seeing that is so attractive. After all, who doesn’t like a guy who is dedicated and driven?

9. Are you close with your family? 

This is important to so many people. Is he close with his 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?

If you’re a big family person and he’s more of a lone wolf, then you know that you might not be very compatible.

10. What show can you watch over and over? 

This question to ask a guy you like will tell you a lot about someone’s sense of humor, which makes a huge impact on how you will get along. [Read: 60 of the most romantic movies in the world that are a must-watch]

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? If you want to be cuddled up on the sofa with this guy after a long day of work, then you need to know what you’ll be watching!

11. 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]

12. What are your dealbreakers in dating? 

These are always good to get out of the way now so that you don’t waste your time. 

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 bother with a second date. [Read: The 25 most common dating deal breakers almost all women agree on]

13. 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.

14. If money wasn’t a factor, what would you be doing? 

This is a great question to ask a guy you like because it reveals a lot in a lighthearted way. Although it may not be realistic or practical, it tells you a lot about someone. 

Would they be doing what they’re doing now? Perhaps they would go on a permanent vacation? Would they spend their time volunteering?

15. What is your biggest pet peeve? 

This could be anything from racism to not putting the shopping carts back, but it can tell you a lot about what people let get to them. [Read: Petty Percy – 18 signs of a petty person that make them so annoying]

16. 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. 

17. 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.

18. Are you more into math 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 about your compatibility.

19. 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]

20. 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?

21. What are you most proud of yourself for? 

This is also a great 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. [Read: How to respect yourself – 37 secrets of self-respect, self-belief, and self-love]

22. What is your favorite book? 

This will let you know their tastes or even if they read books at all!

23. What was your childhood like? 

This is one of those questions to ask a guy you like that’ll reveal his whole outlook toward life as a grown-up. Did he grow up with money or in a more humble manner?

Were his parents together? Did his grandparents raise him? All those show 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]

24. 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? 

25. Who are you closest to in your life? 

Knowing what his personal life is like can tell you how well 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 that he’s close to?

26. 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 so important. [Read: Happily ever after – the psychological benefits of marriage and commitment]

If he never wants to get married and you do, then it’s going to be a very big issue someday in the future.

27. Who do you miss the most? 

His grandma? Or his childhood friend? Maybe 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.

28. 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? 

As dark as this question is, it really helps you learn so much about him and what’s important to him. [Read: Life-altering lessons you can learn from regret]

29. 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 so comfortable sharing with you.

30. 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? 

31. Do you get jealous easily? 

Whether you’ve dealt with a jealous guy in your past or not, you probably know how that can go. It can be very controlling. Is he aware of this? And if so, 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]

32. 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? All these questions are so important to answer.

33. What’s on your bucket list? 

What is so important to him that he wants to do in his life? Does he want to foster dogs? 

Or does he want to visit all the continents? Maybe he wants to make a million dollars in one year? Do you also agree that these things are important? [Read: Couples bucket list and 20 things all couples must try to do]

34. 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, and if so, is he willing to work on them?

35. 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. 

36. Do you believe men and women should be treated equally? 

If he doesn’t say yes, then you know what to do. [Read: Mars and Venus? Very obvious gender differences in communication]

37. 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? If so, can you respect your differences?

38. 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 balanced.

39. 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. 

40. Have you ever been heartbroken? 

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

41. What are your political affiliations, if any? 

Politics can be an iffy subject for couples and if those positions matter to you, then differing opinions here can be a deal-breaker. 

42. Do you trust the government? 

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 from you… you know, wearing a tin-foil hat.

43. 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]

44. Would you adopt or foster? 

To bring up the topic of kids, 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.

45. What is your favorite board game? 

Will you crush him in Monopoly or Scrabble? Knowing this is so important, but only if you want the advantage on game night!

46. 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. [Read: Feminism – what it is, 5 different types and how they differ from each other]

47. Do you recycle, use reusable bottles, or 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 pet peeve that slowly drives you insane, so maybe it’s best to avoid that.

48. What do you do when the power goes out? 

This is another fun question to ask a guy you like because it takes away phones, the 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]

49. 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. 

50. 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 like what you’re ready for, or maybe he is fresh out of a seriously long relationship; if so, maybe he’s not ready to move on.

51. 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: Secret clues your boyfriend is definitely not over his ex yet]

52. 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? If he’s not a very emotional person and you’re very in tune with your emotions, do you think that could cause problems or not?

53. 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? 

54. Have you ever been in a physical fight? 

Is he against violence or will he not let a conflict go unresolved? What was the fight about? If it was about something insignificant and you’re a strong pacifist, you might want to cut ties now rather than get upset later.

55. 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. [Read: Is monogamy for you? How to know your needs and what works for you]

If you two aren’t on the same page with what you would potentially want together, it probably won’t work.

56. 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 and, depending on his answer, are you two compatible?

57. 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?

58. Do you believe in ghosts? 

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

59. 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. In addition, it’s a great way to get a compliment, and who doesn’t love those? [Read: 25 things guys find sexy and very attractive about a girl they see]

60. Who do you look up to the most?  

Does he look up to Gandhi, his mother, or Martin Luther King? Why does this person inspire him?

61. 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 when you find the fandom you’re both obsessed with.

62. Do you prefer summer or winter? 

Sure, 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?

63. Would you travel to space given the opportunity? 

This is quite the conversation starter and a conversation continuer. How far would he go, and would he come back? Does he want to colonize Mars, and if so, does he want you to be there with him?

64. Do you enjoy long car rides? 

This small question to ask a guy you like might not seem like a lot, but it actually does reveal a fair amount of his personality. Will you be going on any road trips or flying just to travel two states over? [Read: 20 fun, unique things to do on a car ride to make it memorable]

65. What languages do you speak? 

This question not only tells 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?

66. 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? This is so an important question to ask, so don’t forget it! [Read: What does a healthy romantic relationship look like? Your guide to building the perfect one]

67. 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.

68. 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.

[Read: 22 early warning signs of a bad boyfriend you need to leave ASAP]

69. Where do you see yourself in five years?

This is a great question because it is relatively soon, but not too far. You will find out if he is ambitious and motivated in his career. 

Generally, this matters a lot, especially if you are career-driven as well. [Read: 50 relationship questions to test your compatibility instantly]

70. What about in ten years?

This question is a little bit more intense because depending on how old they are at the time, this means they will be a real adult, doing adult things. 

If you are even asking, it means you are thinking long-term with this fella, so proceed with caution.

71. What is your biggest accomplishment?

This question tells you about how motivated they are, and WHAT motivates them in life. [Read: Stop being a wallflower and talk to the guy you like]

72. What is your favorite childhood memory?

This is one of those questions to get to know a guy that gives you some insight into what their childhood was like. 

Without digging for answers, you could potentially learn if they had a fantastic childhood, or if it was rough. This allows them to give up as much or as little as they choose, so it’s a pretty safe question to ask on a first date.

73. Who are you closest to in your family?

It says a lot about someone once you know whether they are closer with their mom, dad, sisters, brothers, etc.

If they are closer to their mom or female family members, they could be more sensitive and respectful of women. [Read: Feminine men and 40 signs of a guy who’s more in touch with his softer side]

But if they are closer to their dad or male family members, they could be more masculine and have more difficulty discussing their emotions. The keyword though is “could.”

74. What is your biggest fear?

This could be a funny answer, like mice, or a deep answer, like being forgotten.

75. What is one thing you would never want your parents to know?

Again, this could be something funny, like they had sex in their bed in high school, or it could be that they were addicted to cocaine. Could go either way at this point. [Read: 20 good questions to ask a guy and find out who he really is]

76. Describe your dream life

This is literally the perfect question because you can hear how they envision their future, and you get to decide if you could imagine yourself sharing that life with them or not.

77. If money wasn’t an issue, where would you travel and why?

Everyone really likes talking about traveling, so he will adore this question. It also tells you a lot about a person in terms of the types of landscapes they like, the cultures they’re pulled towards, etc. 

Let’s be honest, if they’re a ski and snow kind of guy and you can’t stand anything below 90 degrees, you’re just not a great match! [Read: Reasons traveling is a great test of compatibility]

78. What is the stupidest thing you have ever done?

This one is just fun, so go on, ask it.

79. Do you have any regrets in life?

Their answer could be “I have no regrets in life because everything happens for a reason” which you could love, or they could tell you some deep, personal things.

80. Share your first kiss story

These are always just embarrassing, awful, and so hilarious. 

81. Share your first “time” story

Well, you might get a surprise here. He may just laugh it off, go into explicit details *in the hope of making you horny!* or you may just find out he’s red-faced because he’s still a virgin! [Read: 28 awkward questions to ask a guy and the weird ones you never should]

82. What would you say is your biggest turn-on about a woman?

Does he describe something about you? SCORE.

83. Your biggest turn-off?

Again, does he describe something about you? …Okay, maybe not a score this time. [Read: The biggest dating turn-offs for guys]

84. What is the hardest thing mentally you have ever had to go through?

He might describe the death of a family member or his best friend… just be prepared here, because it could get very emotional. You might be opening up a fresh wound with this question to get to know a guy. So, proceed cautiously.

85. Describe your perfect partner

He is basically going to hand you everything he is looking for in a partner in a pretty pink box with a bow on it. Does he describe you? Perfecto.

86. What is your ideal first date?

This question gives you insight into his romantic side. Also, this will tell you if he is a down-to-earth guy that just wants to go to the beach or order pizza and watch a movie. 

Or if he is extravagant and wants to take you out to a nice dinner with candlelight and such. [Read: Top 50 amazing first date ideas to wow your date]

87. If someone gave you a million dollars right now, what would you do with it?

Does he give some to charity? Does he keep all of it? Spend it all in a week? Ah, this question to ask a guy and get to know him is just so cliché but it still reveals his inner workings!

88. What’s your guilty pleasure?

Porn? Social Media? Dark movies and shows on Netflix? What is it, and do you have the same guilty pleasure? [Read: 33 guilty pleasures you should keep a secret]

89. How do you imagine your future family?

Does he want children? Can he envisage getting married? Could he imagine family dinners every night, and if so, can you?

90. Who is your role model?

Knowing who he models his behavior after is so important. This will shape the relationship that you might possibly be entering.

91. How would you describe “love”?

Maybe he has never actually experienced love. Perhaps you’ll be his first. Maybe his idea of love is a very superficial, shallow definition. You will learn it all with this question to get to know a guy. [Read: What does it feel like to be in love – 33 must-know truths about being in love]

92. What is one thing that you have learned about yourself from past relationships?

Are you a firm believer in the fact that every relationship teaches you SOMETHING? If he hasn’t learned anything from his past relationships, then perhaps he lacks personal insight, i.e., he does nothing wrong. 

93. Are you a morning person, or a night person?

This is just an interesting question to get to know a guy because perhaps you align in this sense. Both morning people? You can wake up and have breakfast together.

94. What is your favorite animal?

Let’s be honest, a guy who loves animals is instantly more attractive than one who doesn’t. Is it a cute dog or a cat? Is he more about reptiles than cuddly animals? 

95. What trait do you consider the most important in a partner?

Most people will say honesty or faithfulness but it’s interesting to ask. This is one of the more searching questions to get to know a guy because it tells you what is important to him. You never know, he might surprise you. [Read: 20 positive personality traits that can change your life forever]

96. Sex on a first date or not?

A cheeky one but it’s fun to ask! Most guys will say that they don’t want to have sex on a first date but most are lying. If you make it to a date, it gives you a few ideas on whether you want to go there or not!

97. What makes you super angry?

This can give you some very interesting insights into what he can tolerate versus what makes his blood boil. It’s always fun to learn these things and of course, tells you what to avoid!

98. If you could change one trait about yourself, what would you choose?

Nobody is perfect and the fact he can choose a trait tells you that he knows this and he’s working towards self-improvement, in some way at least. 

If he tells you he’s perfect and wouldn’t change anything, he’s lying. [Read: 33 traits of a good boyfriend you should always look for in a guy]

99. What is your favorite movie of all time?

His favorite movies don’t just reveal how he likes wasting his time, but it actually talks about his core values and what makes him who he is. 

Use this question to get to know his favorite movies, and chances are, the lead male characters are people he associates with or aspires to be.

100. Who is your favorite actor?

Is it an action specialist, a deep and meaningful actor, or a comedic genius? This is one of the questions to get to know a guy that will give you a real insight into what he finds entertaining. 

101. Do you really like your job?

This is a loaded question and one that could take the conversation further. He may say that he loves his job and tell you why. Or, he may say he hates it or doesn’t enjoy it generally, and what he would like to do. [Read: Love or career? How to make the right choice]

102. If you could relocate and live somewhere else, then where would you choose?

This is a little like the travel question because it tells you about the types of locations he likes. Again, sub-zero temperatures could be a serious red flag for you, so it’s good to know in advance if he’s drawn to the snow-top mountains!

103. What is your go-to song on karaoke night?

He’ll probably tell you he doesn’t do karaoke but that’s just his ego talking. Push a little further and he’ll buckle under the pressure and admit that he likes “I Will Survive” or something just as cheesy!

104. What was your childhood nickname?

Out of all the questions to get to know a guy, this one will make him smile and take him back to his childhood years.

Just try not to laugh when he tells you what his mom used to call him! [Read: 50 cute things to call your boyfriend to create intimacy]

105. One pillow or two?

Another cheeky one because it gives you pre-information if things were to get intimate! 

106. Ross & Rachel… were they on a break or not?

Even if he wasn’t an avid Friends watcher, he is probably going to understand this debate and will probably also have an opinion on it. Does his answer match yours?

107. If you could have dinner with one famous person, who would it be and why?

Will he choose a beautiful actress just because he can, or will he choose a highly intelligent historian so he can pick their brains? 

Of course, there’s a huge amount of ground between those two examples! [Read: What to look for in a guy – 40 traits that make a man worth dating]

108. Is the glass half full or half empty?

Is he an optimist or a pessimist, are you the same, and if not, then can you live with that?

Wait, don’t you get to know one another slowly over time?

Admittedly, yes, but having a little pre-information is never a bad thing. After all, why waste your time on someone just to find out that you’re not going to get along with them? 

By asking some questions to get to know a guy, you can work out whether this is a guy who is worthy of your time and attention, or someone you should pass on. [Read: How to get to know someone on a date]

Getting to know one another over time is a totally different type of familiarity. That’s all about making memories together and growing as a new couple; that takes so much time.

But by asking these pre-dating questions, you can work out whether you’re really suited for the long run. 

Do you have the same values? Does he like animals? What is his favorite color? You know, all the important things in life that you have to know! [Read: 24 secrets to talk to your crush and get them to fall for you in no time]

Of course, one thing you shouldn’t do is make him feel like you’re interviewing him. That’s not cool or fun. 

If you’re going to go down the quick-fire question game, fair enough, fire away, but make sure he knows it’s a game and not a grilling he wasn’t pre-warned about!

Why should you ask a guy these questions?

When you are trying to get to know someone, how else can you do it than by asking them questions, right? [Read: 27 happy, fun questions to ask a guy to make him laugh and smile around you]

If you don’t ask him any questions, then you will only talk about external things like the weather or the current political situation in the world.

But those kinds of generic questions won’t let you get to know him as a person. Sure, they could be interesting conversations, but they shouldn’t replace the more personal ones that will help you dig deep with him.

Also, these questions will also help you figure out of the two of you are compatible. Too often, people start dating and forget to ask the hard *and fun* questions to see if they would work out long-term. [Read: 196 fun and deep relationship questions to test your couple compatibility]

So, that’s why you need to ask these questions of a guy you like! 

What should you be mindful of before asking questions?

While asking a guy you like all these questions is important and helps you get to know him better, that doesn’t mean you should ignore social cues. So, you have to pay attention to and be mindful of the following things before you start asking questions.

1. Timing

If you just met the guy or it’s a first date, you don’t know him, so you might not want to start digging too deep with your questions right away. Some people – especially guys – aren’t very comfortable sharing personal details or their thoughts and ideas. [Read: 19 secrets to not be shy around your crush and talk casually]

Of course, you can ask some light-hearted questions early on. But save the deeper ones and the ones about the future *like starting a family* until later on. You don’t want him to feel uncomfortable or that you’re trying to pry.

2. Read the room

“Reading the room” is basically just a phrase that says that you need to take contextual cues into consideration before you say and do anything. [Read: Male body language – 48 signs to instantly read a man’s mind]

For example, you probably wouldn’t tell a dirty joke to your grandma, but you would to your best friend.

So, when you’re “reading the room” with a guy you like, just try to stay tuned into his body language and other nonverbal cues. If his face or posture tells you that he’s getting uncomfortable, then back off. If he seems to be enjoying it, then keep going.

3. This isn’t an interrogation

Remember, this isn’t an interrogation or interview so you don’t want to make it feel like one. He’s not some criminal or candidate for a job interview after all! [Read: How to talk to a guy – 40 secrets to sweet talk and make him like you]

He’s a guy you like, so you just want to get to know him better!

So, don’t pull out your list and go question by question. Instead, you want to weave these questions into your conversation easily and effortlessly. You have to make him feel like it’s just a fun conversation that you’re trying to have with him so that he doesn’t feel under pressure and, you know, make a run for it!

Getting to know him better

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 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. 

[Read: 60 fun get-to-know-you questions to know your new romantic partner]

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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Vinod Srinivas Serai
Vin Serai
Vin Serai is the founder of LovePanky.com, and has delved deep into the working of love and relationships for almost two decades. Having dipped his feet in almo...