70 Questions To Ask Your Crush And Know Him Better

Talking to the person you’re crushing hard on can be a nerve-wracking experience. Even if they’re clueless about the way you feel about them. If only there was a list of questions to ask your crush you could refer to!

A handy guide that can make the conversation flow and help you get to know him better. Ever found yourself secretly wishing for this? We feel ya! After all, haven’t we all been there? Forget coming up with suave, intimate questions to ask your crush, it seems hard to get past ‘how are you doing?’ and ‘what’s new?’

To bail you out of your tongue-tied state, we have compiled an elaborate list of 70 questions to ask your crush to get to know him. Read on, keep it handy, and brush up before you meet your crush next.

Good YOLO Questions To Ask Your Crush

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All you millennials and Gen-Zers out there already know what we mean when we say YOLO. Boomers and Gen X peeps, take note: YOLO means You Only Live Once. Is your crush someone who lives in the moment? Or are they the kind to meticulously plan their course of life and stick to that plan come what may? Knowing the right YOLO questions to ask them might just be the key to striking a chord with them.

Besides, finding out the answer to these questions can tell you whether or not you both will be compatible as romantic partners. If you’re spontaneous and they’re not – or vice-versa – it can turn out to be quite the dampener. So, use these YOLO questions to ask your crush and you shall have your answer about whether or not you will fit in like a hand in glove:

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1. Do you believe in fate?

If you’re looking for Yolo questions to ask your crush, lead with this. It’ll give you a fair idea about whether your crush is a realistic, agnostic, believer or someone who attributes the course of his future to the workings of a higher power.

2. If you had only one day left to live, how would you spend it?

Their answer will tell you a lot about his priorities, ambitions, desires, hopes, dreams and aspirations. With this single question, you can gain a sneak peek into the deepest recesses of his mind.

3. Carpe diem or not?

Is your crush a seize the day kind of a guy or does he like to plan his life down to the last detail? Add this to your list of Yolo questions to ask your crush to find out.

4. What is the greatest adventure you’ve embarked on?

Skydiving? Deep-sea diving? Bungee jumping? His answer will tell you how far he is willing to go for a good adrenaline rush. Are you ready for such extreme adventures?

5. What is the one fear that holds you back?

A person’s fears are among their most intimate thoughts. Something that is not easily shared. That’s why this is one of the great YOLO questions to ask that will truly help you get to know him better.

6. What is the one bad decision you don’t regret making?

Almost everyone carries the emotional baggage of bad decisions they regret in hindsight. Your crush isn’t an exception to this near-universal phenomenon. If you want to understand him on an intimate level, don’t miss adding this to your repository of questions to ask your crush.

7. If you could have any animal as a pet, which one would you choose? And why?

A dog? A cat? A dragon? His reply will tell you a lot about his personality. For instance, if he chooses a dog, he values affection, companionship and loyalty. If he chooses a cat, he is more of a free-spirited person who values his independence greatly. And if he chooses something as outlandish as dragons, you know that there is a fantastical streak to him.

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8. Would you ever go skydiving?

Jumping out of airplanes is definitely now for everyone. If he responds to this question with an animated excitement, you’d know that you can expect being with him to turn out to be the most thrilling experience of your life. Given that things progress between you two, of course.

9. Would you ditch an important work commitment for a trip with your friends?

This is among the fun yet intriguing Yolo questions to ask your crush. If he is up for ditching an important presentation at work to go on an impromptu road trip with his friends, you know that there is a whimsical side to him. This can be a good thing or bad depending on your own take on life and responsibilities.

10. If you had 10 million dollars, how would you spend it?

Looking for unmissable YOLO questions to ask your crush. We strongly recommend you add this one to the list. Let’s hope he doesn’t say, “Invest it.” Could there be a more snooze-inducing answer to this fun scenario that is replete with possibilities!

Subtle Questions To Ask Your Crush

Settle the curiosity about private aspects of your crush’s life
Settle the curiosity about private aspects of your crush’s life

You may be curious about some rather sensitive or private aspects of your crush’s life. But you haven’t asked him about any of it yet for the fear that you can come across as too forthright or nosy. That may scare him or put him off.

Your apprehension is spot on too. Not many people are comfortable opening up to others about things closest to their hearts. What if we told you that you could fish for answers subtly and put your curiosity to rest.

Intrigued? Pay attention to these subtle questions to ask your crush to uncover the layers of enigma surrounding them:

Related Reading: 30 Interesting Questions To Ask A Girl To Know Her Better

11. Is there an experience that influenced you deeply as a child?

Want to understand why your crush behaves a certain way in certain situations? Do you suspect that there may be some underlying emotional triggers at play but don’t want to ask him that upfront? That’s where such subtle questions to ask your crush come in handy.

12. Have you ever been in love?

Our experiences with love shape our personalities
Our experiences with love shape our personalities

Our experiences with love have a lot of bearing on our personalities. That’s why this is among the important questions to ask your crush to get to know him.

13. Why didn’t it work out?

The fact that he is now single and there is this thing brewing between you two is proof that his past love story or stories didn’t pan out well. Don’t hesitate in asking him why. The right subtle questions to ask your crush can offer you great insights into his personality and the inner workings of his brain.

14. How have you dealt with heartbreak in the past?

Heartbreak is a crushing experience that changes people on a fundamental level. Commitment issues, trust issues, giving up on love are all outcomes of heartbreak. In light of all this, this becomes one of the most crucial subtle questions to ask your crush to understand if he is ready for a relationship. Or ever will be.

15. Do you believe in soulmates?

Whether or not your beliefs regarding soulmates converge or not can have a significant bearing on your compatibility as a couple. This is among the subtle questions to ask your crush that can serve as a covert compatibility test.

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16. Have you ever fallen in love at first sight?

Even if this happened when your crush was a teenager, it can make for a cute story that will help you see the soft, mushy side of your guy.

17. Who is the one person you value the most?

This is one of the subtle questions to ask your crush that will instantly tell you how much he values relationships in his life. Besides, giving you a clear picture of people in his innermost circle.

18. What is your vision for your life?

How does your crush envisage his life to be? Is he someone who’d chase the societal benchmarks of success and prosperity or is he happy doing his own thing? Use these subtle questions to ask your crush to know what is it that he truly desires (insert Lucifer Morningstar’s drool-worthy accent).

19. What was your first impression of me?

Subtly weaving this question into a conversation can help you understand what he thinks of you and what are the odds of you both ending up together.

20. Are you looking for a long-term commitment right now?

Want to know whether or not your man is a commitment-phobe? Don’t miss out on this question. Now, just because he says that he is not ready for long-term commitment doesn’t mean that he fears it. But if the mention of the word commitment makes him jump out of his skin, then that’s a definite red flag that shouldn’t be ignored.

Provocative Questions To Ask Your Crush

How does your crush react when provoked, cornered or put in a tight spot? If you like him enough to consider taking this attraction to the next level, it’s best to find out these often well-masked details. That way you can be sure that there are no unpleasant surprises later.

Take your mutual attraction to the next level
Take your mutual attraction to the next level

Like, them crashing an exquisite vase to bits because you referred to their favorite team as a bunch of losers. Be warned though, asking provocative questions can inspire some passionate responses. And may even lead to heated arguments. You have to be sure that you share a certain comfort level with this person before taking the plunge.

When timed right, these can turn out to be stimulating and good questions to ask your crush. If you’re ready, here is a rundown on provocative questions to ask your crush:

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21. Democrats or Republicans?

Political beliefs are undoubtedly among the most provocative questions to ask your crush. Be warned that a heated discussion (read argument) may ensue if you’re both on opposite sides of the political divide. You have to risk venturing into such questions to ask a crush to get to know them.

22. What are your views on climate change?

Want to know whether or not a crush is worthy of all the attention you’re giving him? Ask him this question. You definitely don’t want to waste your time fawning over someone who considers climate change a matter of ‘belief’ rather than a hard scientific fact.

23. Do you believe in God?

This can also prove to be a volatile topic, which makes it qualify among the provocative questions to ask your crush. People are often staunch in their religious leanings, even if it is an absolute lack of belief in the existence of God. That is precisely why this becomes an important point of discussion.

If you cannot bring yourselves to agree or at least agree to disagree with each other’s religious views, there is little hope of forging a healthy relationship.

24. Lakers or Bulls?

After all, isn’t sports a religion unto itself! That’s why this is among the most important questions to ask your guy crush to know where their loyalties and passions lie.

25. Do you think Inception was overrated?

There are two kinds of people in this world – those who worship Inception as a cult classic and those who cannot bear to stand. Ask this fun yet provocative question to ask your crush to see which side of this divide you’re both on. And if your opinions on the matter are the same, you may have just found yourself a match made in heaven! Don’t let him go.

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26. What are your thoughts on reincarnation?

Does he believe in the cycle of rebirth, the continuance of the soul and the like? Or does he think that once you’re gone, you’re gone? And what about you two? This is one of the questions to ask your crush that can inevitably prove to be a compatibility test of sorts.

27. Would you describe yourself as a feminist?

Anyone who treats feminism as a dirty word is bad news. You cannot hope to build a partnership of equals with such a person. It’s better to swallow your feelings now than to be heartbroken later. That’s why this is among the questions to ask your crush to get to know him.

28. Are you a supporter of LGBTQ rights?

This is another one of the provocative questions to ask your crush that will help you understand his worldview. More importantly, it’ll help you understand if he is capable of empathy, respect and compassion.

29. What are your views on racism?

Now, you don’t want to be fawning over someone who hangs the Confederate flag on their front lawn. Do you? The world needs freedom from fear and hate of otherness now more than ever. Finding that in a potential partner should be non-negotiable.

30. Capitalist, Socialist or Communist – your idea of an ideal societal structure?

Now, there are no right or wrong answers to this question. After all, each of these systems has its share of flaws and shortcomings. Even so, this is one of the questions to ask your crush that will help you get to know him better.

Edgy Questions To Ask Your Crush

If you’ve tried your hand at subtle questions and hit a wall, it may be time to up your game. Change gears on your get-to-know-your-crush quest and add a little edge to your conversations.

Add a little edge to your conversations
Add a little edge to your conversations

Here are some edgy questions to ask your crush that will hit the nail on its head and give you a sneak-peek into their innermost thoughts:

Related Reading: 36 Relationship Building Questions To Ask Your Partner

31. What makes you nervous?

What ruffles your crush’s feathers, leaving them unsettled and overcome with butterflies in the stomach? You will definitely feel a little closer to him when you learn such intimate details of his personality. Such questions to ask your crush while texting can truly breathe freshness into your conversations and help you get to know each other more intimately.

32. Would you rather have love or money in your life?

Our priorities define what course our lives are going to charter. That’s why it becomes one of the most important intimate questions to ask your crush.

33. What has been your most bizarre life experience?

This can definitely be used as a conversation starter to help you move from awkward silences to easy-flowing chatter. Surely, this question will bring up some interesting anecdotes that you can share with each other.

34. Do you believe in karma?

If he does, he’d definitely be a conscientious person who thinks about the impact of his actions on others rather than going through life mindlessly. And that’s an admirable quality to have. His response to this question might just give you another reason to like him even more.

35. What is the best piece of advice you’ve ever received?

Who knows maybe that advice will resonate with you too and give you a new perspective on handling precarious situations in life. The right intimate questions to ask your crush can truly cement the bond you share, and this is just one of them.

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36. What would be the five deal-breakers for you in a relationship?

This is one of the edgy questions to ask your crush that you just shouldn’t miss out on. A discussion about relationship deal-breakers will help you understand what he expects from a partner and assess whether these expectations align with your own.

37. Have you ever cheated or been cheated on?

A brush with infidelity can change a person's view of romantic partnerships
A brush with infidelity can change a person’s view of romantic partnerships

Incidents of infidelity are hard to recover from. Even if a person succeeds in moving on, it can change their view of romantic partnerships forever. That’s why this is among the most crucial relationship questions to ask your crush.

38. What is the biggest turn off for you?

Now, this is undoubtedly something you ought to know about the crush so that your actions or mannerisms don’t inadvertently make you come across as undateable. Intimate questions to ask your crush can also help you understand how to woo them better. So, use them to your advantage.

39. Who is the one person you’re closest to?

His mom? Best friend from high school? His ex? The answer to this question will give you clarity about a host of things. For instance, if he names a former partner, you can be certain that he is not over his ex. In that case, there is no point in pursuing a person who is already invested in someone else.

On the other hand, if he gives you the name of someone else in their life, you’d know that earning brownie points with this person will definitely prop up your perception in his eyes.

40. If you got a do-over, what’s the one thing you’d change about your life?

Is he content with the way his life panned out or does he have regrets so imposing that he’d like to do it all over again? This question will help you understand. Among the many good questions to ask your crush, this is one you shouldn’t let slide.

Thoughtful Questions To Ask Your Crush

When you want to get to know the other person on an intimate level, small talk and casual questions will not take you very far. So, if you feel strong affection and admiration for your crush, you may want to connect with them on a deeper level.

That means getting to know their darkest fears and deepest desires. Learning about what keeps them up at night and what makes them tick. Their passions, dreams, goals, hopes and aspirations. And so much more.

These thoughtful questions to ask your crush will help you do just that:

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41. Do you feel appreciated and loved?

A person who feels appreciated and loved will definitely have a more positive outlook on life as compared to someone who feels undervalued. In the case of the latter, you may well have fallen for a man with low self-esteem.

42. What is the one thought that keeps you up at night?

This is among the thoughtful questions to ask your crush that will help you reach the deepest recesses of his mind. That’s why it counts among the good questions to ask your crush because it will instantly make you feel like you understand him better.

43. Have you ever felt lonely in life?

Being alone and lonely aren’t the same things. How does your crush view his single status? Does he feel lonely in his single life? Or is he content? Ask this question to find out.

44. What is the one loss you’ve been able to come to terms with?

The grief of losing a loved one – whether it is a family member, a friend or even a pet – can become a permanent weight on a person’s soul. If your crush has been through something like that, knowing about it will help you understand him better.

45. What are your three top life goals?

Understand his priorities
Understand his priorities

This is one of the thoughtful questions to ask your crush that will help you understand his priorities and vision for a ‘happy, wholesome’ life. Do take a moment to reflect on whether or not you both want the same things in life.

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46. Do you feel strongly about a cause?

If you both feel strongly about the same or similar things, it can give you more common ground to connect over. That’s why this is one of the questions to ask your crush that you should not miss out on.

47. How would you describe yourself to an absolute stranger?

His answer will give you a unique perspective on how your crush views himself. Is he confident and self-assured? Or is self-conscious and sells himself short? It’s near impossible to find out these things about a person you don’t know inside out without such thoughtful questions to ask your crush.

48. Do you find silence comforting or unsettling?

Another one of the great questions to ask your crush while texting. Only a person who is at peace with himself can find comfort in silences. His answer will give you an assessment of his state of mind.

49. What, according to you, makes this world a beautiful place?

This is among the thoughtful questions to ask your crush that will help you understand his worldview. And also help you understand whether you can look at the world from each other’s prism.

50. Has your life panned out how you envisaged it to be?

This is one of the questions to ask your crush to get to know him better that you just shouldn’t miss out on. This can open the floodgates for some intimate, heart-to-heart conversations.

Smooth Questions To Ask Your Crush

Not all conversations with your crush have to be deep and thought-provoking. After all, putting one’s life under the lens can get heavy and distressing. To keep your crush invested in the conversation, you have to learn to mix it up.

These smooth questions to ask your crush will help you change the mood and still offer you some interesting insights about their life:

Related Reading: If you love someone: Tell them. Here’s why.

51. What is the kindest thing someone has done for you?

Even the smallest acts of kindness can touch us in unimaginable ways and leave a lasting impression on our hearts. Learning about these finer details of your crush’s life is what will truly help you understand who he is.

52. How old were you when you moved out of your parents’ house?

Slip in such smooth questions to ask your crush casually into conversations to understand his independent streak.

53. What is the one thing you love about your job?

Is he passionate about his job or just in it to earn his paycheck? Your crush’s response will help you understand where his passions truly lie.

54. What was college like for you?

College days have a transformative effect on our personalities. If you want to understand your crush well, this is definitely a part of his life you should revisit.

55. Do you have a large social circle or an intimate group of close friends?

Is he a party animal or a homebody? His answer to your question will help you understand whether your lifestyles will match.

56. Which book are you reading currently?

This can lead to some intellectually stimulating conversations
This can lead to some intellectually stimulating conversations

This qualifies as one of the important smooth questions to ask your crush, as it can open the doors of some deep, thoughtful conversations. It also makes for a great way to build intellectual intimacy with your crush.

Related Reading: 22 bad habits that ruin a relationship

57. Which movie can you watch over and over again?

If your taste in movies does match, you can definitely use it to your advantage. Plan a movie marathon with both of your favorite flicks of all time, and you have the perfect excuse to spend some quality time with your crush.

58. Have you ever made a complete fool of yourself in public?

Throwing up in a club, making a fool of oneself in trying to win over a crush, drunk texting the wrong person…everyone has at least a handful of such embarrassing stories in their kitty. Get him to spill the beans and you’ll have something to share a hearty laugh over.

59. Which section of the newspaper do you read first?

It may seem like a generic or inconsequential question but it can help you discover some lesser-known things about your crush that don’t come up in day-to-day conversation.

60. What is the one daily ritual that you never skip?

This is among the smooth questions to ask your crush that will give you an insight into what his routine is like without even having stepped into his world.

Intriguing Questions To Ask Your Crush

The strange thing about people is that no matter how well you think you know them, there is always more to find out. Sometimes, you have to go on a tangent to uncover some of the carefully tucked away details of a person’s life.

You can make them curious about you as well
You can make them curious about you as well

In the process, you can make them curious about you as well. Sounds promising? Put these intriguing questions to ask your crush to good use and discover more lesser-known facts about them:

Related Reading: 22 Ways To Know If A Guy Secretly Loves You, But Is Too Shy To Admit It

61. What was your most erotic intimate experience?

Don’t shy away from such intimate questions to ask your crush if you truly want to know him like the back of your hand. If things do progress between you two at some point, his response can serve as a yardstick to your journey of intimacy with him.

62. What is your pet peeve?

This is among the intriguing questions to ask your crush that will bring out his quirks and idiosyncrasies. Brace yourself for some rather surprising revelations.

63. Have you ever been curious about your sexuality?

Has he experimented with his sexual leanings? If so, what was the experience like? These are some good questions to ask your crush that can help you see a side to him that not many may be aware of.

64. Have you ever been in an open or polyamorous relationship?

If he has been in an open relationship, a discussion on his views on monogamy is warranted. If that’s something you value and he doesn’t, making a relationship work in the future can become a challenge.

65. What cartoon character do you identify as?

This is just a fun question that can lead to some light-hearted banter or animated discussion about different characters. You can count on such fun questions to ask your crush to figure out how well you can vibe with him.

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66. What is your spirit animal?

This is among the intriguing questions to ask your crush that will surely have him racking his brains for an answer. And of course, his reply will mirror his sense of the self. So, this seemingly innocuous question can lead to some insightful revelations.

67. Do you believe in astrology and zodiac signs?

Does he believe that zodiac signs impact our personalities? Depending on your own views on the matter, his response can make him seem more charming or put you off totally.

68. Do you have trouble apologizing for your mistakes?

The inability to open up one’s mistake is the hallmark of an egotistical person, with possible narcissistic tendencies. And must be viewed as a red flag.

69. Can you forgive easily?

Forgiveness is essential to building harmonious relationships, romantic or otherwise. That’s why this becomes one of the most important questions to ask your crush, especially if you’re seriously considering getting into a long-term relationship with them.

70. Can you live without the internet?

Is your crush addicted to technology and gadgets?
Is your crush addicted to technology and gadgets?

It’s just one of the lighter questions to ask your crush to understand how dependent he is on technology. After all, you don’t want to end up with someone who lives their life with their face buried in a screen and have your relationship ruined by ‘technoference’.

After you’re done with these questions, you will know your crush like the back of your hand. And have a clearer idea about how well-suited you are for one another. However, use them tactically. Don’t throw a barrage of questions at your crush at once, making them feel like they’re being held for some interrogation. Weave them into your conversation seamlessly, and build upon their responses to truly understand what they’re like.

FAQs

1. Why is it important to know your crush well?

It helps you decide whether or not you should act on your feelings and take things to the next level.

2. What if I don’t like what I hear?

Then, you must work on getting over your crush and keep your mind open to other alternatives.

3. Will these questions tell me whether my crush likes me back?

If they’re happy to indulge you, chances are the feelings of attraction and admiration are mutual.

4. Can I ask all these questions at once?

No, you must use these questions tactfully so as not to alarm your crush or make them feel cornered.

5. What if he asks me similar questions?

Respond openly and honestly. He has an equal right to get to know you well.

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