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Questions To Ask A Guy You Like - featured

76 Best Questions To Ask A Guy You Like - Ask these now.


Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on, iHeart Media, Elite Dai ...
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by | September 2nd, 2021

Gals, it's a common thing to wonder about questions to ask a guy you like.

Have you ever wondered how to start a conversation with a guy? Maybe you're ready to consider how to flirt with a guy. Everyone wants to find their match and figuring out how to get a boyfriend is a topic that's on lots of gals' minds.

Our carefully curated lists of questions to ask a guy you like will give you the confidence and inspiration you need to have greater intimacy in all your relationships.


10 Best Questions To Ask A Guy You Like

The best questions to ask a guy you like are far will make him think and reflect on himself.

Here are the 10 best questions to ask a guy you like:

1. What does your dream house look like?

Does he care about presentation and appearance or is he environmentally mindful? Frankly, a person's dream home being too consumptive or ego-seeking in nature might be the red flag you need to figure out whether to proceed.

2. Do you believe in making New Year resolutions?

You'll get a grasp on how his outlook on goal-setting, commitment, and this tradition comes with its own set of controversies.

3. What Makes You Unique?

It's a very open-ended question. The level of honesty he puts in his answer will tell you how much he thinks for himself vs. how tied down he feels to telling you the answer he thinks you want to hear.

4. What’s Your Favorite Place on Earth?

Does he think of the great outdoors and nature's magnificence or does he choose places based on community and people? You might note his introversion or extroversion.

5. What’s the best thing about your life right now?

The way a person perceives and learns from his experiences that might be frustrating for some and enlightening for others will show you whether he's a glass-half-full or glass-half-empty kind of person.

6. If you could only watch one movie for the rest of your life, what would it be?

The movies that resonate most with us tend to contain remnants of past life memories.

7. Could You Live Without The Internet?

Beyond just yes or no, what is his level of dependency on the information superhighway? Has he been able to recall how the world is without social media?

8. What’s the stupidest thing you’ve ever done?

Humility and humbleness and ability to learn from mistakes will be revealed here.

9. What’s one thing about yourself, personality-wise, that you like?

Does he really know himself? Does he feel social or cultural pressure to self-deprecate? Is he accurate in his assessment of his personality?

10. If you had to describe yourself in three words, what would they be?

Cliche word choices like "open minded" and "spontaneous" vs. carefully conceived adjectives will tell you how in touch he is with himself and how much he believes he needs to present a certain image of himself.

14 Get To Know You Questions To Examine A Guy You Like

Eventually, your conversation will flow extraordinarily well or the level of awkwardness will reach such levels that both of you know it's not a go.

In the interim, some get to know you questions to ask a guy you like will help.

Here are 14 get to know you questions to ask a guy you like:

11. Which according to you is a ‘must watch’ movie of all time?

A must-watch movie contains a universal message that is so complex it requires a plot to fully deliver. You may figure out what he most wants the world to know about life and love and human nature.

12. What are your favorite breakfast items?

You'll know what to cook when you start making meals for each other.

13. What is your staple party dish?

Is it chips and salsa or more refined pigs in a blanket?

14. If you could change anything about the way you were raised, what would it be?

This is one of the best questions to ask someone you like if you really want to know more about them. We cement our core values often because they are in direct, abrasive contrast with those of our parents.

15. Have you ever been out of the country?

A person's reiteration of cultural understanding beyond their own says everything about the flexibility of their mind.

16. If you didn’t have to work to support yourself, how would you spend your time?

For some, the line between work and play is intangible. For some, the two are wholly separate.

17. What does a typical day look like for you?

Our mundane activities are often some of the most telling and fascinating parts of us. See if he has the confidence to know this about yourself.

18. How often do you pray?

Who does he pray to and what are his beliefs about prayer overall? Is it a time to ask for stuff or to unfold the extent of his gratitude for the infinity of each moment?

19. Is there anything you don’t eat?

Diet says everything about lifestyle and values these days.

20. Does your family still live in your hometown?

Lineage and roots are huge parts of identity.

21. What do you think of public displays of affection?

Get on the same page regarding how you'd both like to interact with each other in public and how seamlessly that flows into private intimacy.

22. Do You Have/Have You Ever Had Any Pets?

How a guy treats his animals says everything about how he treats people in his life and how he treats himself.

23. Have you ever been arrested?

If he was arrested for political protest for something worth it, it might be an indicator of valor and courage more than criminality.

24. What Are You Kind Of Obsessed With These Days?

Our obsessions are not things to feel guilt or shame over. See if or how he hides guilt or shame around whatever he's obsessed with. Note if he can balance daily responsibilities with obsessions.

11 Funny Questions To Quiz The Guy You Like

Sometimes when we're feeling awkward, it can be hard to tap into the sense of humor that we easily demonstrate with our close friends and family. To help you along, these funny questions can help break the ice.

Here are 11 funny questions to ask a guy you like:

25. Which of the Seven Dwarfs is most like you?

See if he's willing to put you at ease by being self-deprecating.

26. Do you love freebies?

Find out what the funniest or weirdest freebie is he's ever received.

27. Which TV family is most like your own?

Metaphors are fast track ways to get tons of information.

28. What was your biggest “what was I thinking?” moment?

See how he processes regrets and whether he can extract the humor and wisdom from it.

29. If you were wrongfully put into an insane asylum, how would you convince them that you’re actually sane and not just pretending to be sane?

Or, what would they do first to experience the insane asylum before making a break for it?

30. Which body part do you wish you could detach and why?

All of us have some part of us that gives a little trouble. Whether an achy back or cracking knees.

31. When did you screw everything up, but no one ever found out it was you?

How good are they at not getting caught?

32. If you had to become an inanimate object for a year, what object would you choose to be?

You could replay the Be Our Guest part of Beauty and the Beast for inspiration.

33. Do you sleep with your legs tucked under the blankets or one foot out?

You know, for oxygen.

34. Do you have to have your closet doors open or closed when you go to sleep?

Since Mike from Monsters, Inc. could jump out at any moment.

35. Have you ever sent a text or email to the wrong person? What happened?

Hopefully it was an automated no reply email and it bounced back... or didn't it?

7 Random Questions To Interrogate A Fella You Like

We love to ask random questions because their unexpectedness generates creativity which in turn, reprograms us to believe something new and never experienced before is about to happen.

Here are 7 random questions to ask a guy you like:

36. If you opened a store, what would you sell and what would be its name?

His answer will tell you what he believes the world needs more of. In this age of unicorn start-ups, his products might not even be physical or tangible.

37. If you could invent a holiday, what would it be?

What thing in life does he think needs more honoring and remembrance?

38. If you got to choose your name, what would it be and why?

Names carry power. The number of syllables and repetition of letters in the name can also have significance that we feel in our gut that can't be explained.

39. If you were arrested with no explanation, what would your friends and family assume you had done?

How open is he to admit his loved ones know his patterns and hindrances?

40. What is holding you back from being the person you want to be?

This question and its most honest, thoughtful, authentic, audacious answer is the most important and telling question you will ever ask another person.

41. What aspects of humans have made us a successful species?

You can turn that around and be more honest and replace "successful species" with "cancer on the planet" too.

42. What is a miracle that happens every day?

A man's ability to recognize miracles in the mundane is one of the most integral and crucial things to look for in a worthy partner.

7 Interesting Questions To Quiz The Man You Like

These cool interesting questions to ask a guy are sure to make you feel ready and empowered, whether you're speed dating or you're looking for ways to make a night last forever.

Here are 7 interesting questions to ask a guy you like:

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

We hope for a man who isn't automatically made self-conscious by this question. Embrace a guy who has the confidence to dive right into the idea of expressing his feminine side.

44. Do you think we've met before in a previous life?

Spiritual connections are very real and we need not be afraid of discussing our belief in them. Science and spirituality affirm each other and one does not negate the other.

45. Are you a fan of the Harry Potter series?

These are such complex, amazing stories and they contain metaphors for every facet of human existence imaginable.

46. What is the weirdest thing you have seen in someone else’s home?

A chainsaw by someone's bed could mean he's a woodworking artist or will surely murder you in your sleep. Loudly.

47. What Do You Think About When You’re By Yourself?

A rich inner life is a definite green light.

48. Would you ever consider skydiving?

Maybe he's done it lots of times. It's really not hard to do a beginner jump with an instructor but skydiving is used as some sort of social yardstick to measure courage.

 49. What is A Smell That Takes You Back To Your Childhood?

Olfactory alive!

6 Personal Questions To Ask A Lad You Like

Beating around the bush is annoying and exhausting after awhile and you'll need some deep personal questions to ask a guy if you are to truly discover compatibility and gain your own self-awareness in the process.

Here are 6 personal questions to ask a guy you like:

50. Do you keep in touch with your parents and siblings?

Note your own judgment or lack thereof regarding this. Some folks have dysfunctional families and keeping a distance from them might actually be a sign of healthy boundaries.

51. Do you feel your parents treated you and your siblings the same or was there favoritism?

Family systems dynamics create core wounds that partners need to be aware of so they can support each other as each individual works through their own.

52. Do You Believe In Second Chances?

Forgiveness, in general, is a green light. Especially an understanding of what forgiveness for oneself actually means.

53. How often did you go on family trips?

Were they chances to unwind and create greater intimacy? Were they the source of a lot of family arguments?

54. Is there a black sheep in your family? What is different about them?

Kudos if you are dating that black sheep. The black sheep is often the wisest and most awake of them all.

55. Are you so close to any of your friends that you consider them to be like family?

We have the intimacy that is taught to us. And we have the sort of intimacy in friendships that we create based on whether we were nourished or traumatized by family intimacy.

8 Deep Questions You Ask To A Man You Like

Get to know your guy immediately at first encounter and far into your relationship with these personal and deep questions to ask.

Here are 8 deep questions to ask to ask a guy you like:

56. What, if anything, is too serious to be joked about?

We hope for a guy with class, manners and boundaries and awareness of the power of words.

57. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

Does he fear the future? Does he fear being swayed beyond masculine logic by the esoteric?

58. Have you ever made a decision that changed your entire life? If so, what was it?

With what strong arm is he steering his own ship and what value does he realize in it?

59. Do you think crying isn't a manly thing to do?

Advocate for a modern man who has no such outdated beliefs about gender-specific emoting.

60. What Did You Always Wanted To Try But Never Found The Courage To Do?

How aware is he of the limitations he puts on himself and what old beliefs need updating?

61. What’s invisible but you wish people could see?

We all wish to be seen in ways that get overlooked. Give him his chance to request acknowledgment. It will inspire him to support yours.

62. Till What Age Would You Like To Live And Why?

This may be less about a number and the quality of life in old age that we imagine tolerating.

63. What would you have done differently if you were given a chance to go back in time and reduce your carbon footprint?

Environmentally aware questions say everything about a man's character and regard for the feminine.

3 Questions You Can Ask Over Text

If you really like a guy, then you should strive to make a great impression with these excellent questions to ask a guy over text.

Here are 3 questions to ask a guy you live over text:

64. How do you know when you really, really like a woman?

Ask this question, and you can discover a guy’s romantic side that might’ve been hidden previously.

65. Are you more attracted to people who have the same traits that you do or those with opposing ones?

This is an important question to ask, especially if you’re not sure whether two people so different can be in a relationship together.

66. Are you active on social media, or do you prefer to be more private?

This is another important question to ask a guy, and it’ll share whether you two have similar values.

3 Flirty Questions You Can Ask Your Man

Flirting with a guy you like is a little different because you need to choose flirty questions to ask a guy that are guaranteed to work.

Here are 3 flirty questions to ask a guy you like:

67. How would you describe your perfect girl in five words?

This is a great way to flirt, because he’ll probably end up describing you if he feels strongly about you.

68. How and when would you know the right person for you?

He’ll probably have to think pretty hard about this question… or maybe he already knows he’s found the right person…

69. At what age do you plan to get married?

Make sure he knows you’re interested by asking this question, and discover whether you two share the same plan in the process.

7 Fun Questions To Ask Your Lover

Keeping it fun and light is a great way to make sure a guy remains interested, especially if you choose fun questions to ask a guy.

Here are 7 fun questions to ask a guy you like:

70. What is your favorite season of the year?

Certain seasons are really romantic, but different people have different tastes. Find out what he thinks.

71. Are you a jealous person? How does it show?

Most guys might not want to admit it, but jealousy is pretty common. Finding out more is a fun way to get him to open up.

72. What would be the funniest thing to fill a piñata with?

Random questions are sometimes the best for breaking the ice, and he’ll have plenty of fun answering this one.

73. If you were the President for a day, what would you change in the world?

It's fun to see whether he'd act crazy or logical if he ever became president!

74. How do you deal with rude people?

Finding out how he deals with rude people is often pretty funny. People can get pretty creative when they just don't want to deal with someone anymore.

75. What kind of people do you find easy and hard to get along with?

This question also reveals a lot about his personality. You'll also get a sense of who his friends might be, which is important when starting a relationship.

76. If you are an author, what book would you write?

Even if a guy has no intention of ever writing a book, most can at least brainstorm a few ideas - and they're often hilarious.

Downloadable list of Questions To Ask A Guy You Like

Here is a downloadable and printable List of questions to ask a guy you like (right click the image and select Save Image As…):

How to Pick The Best Questions To Ask A Guy You Like

There are some important things to do before asking the guy you like these questions. Learn the steps below.

Here is how to pick the best questions to ask a guy you like:

1. Ask questions to reveal his level of self-awareness

Some people believe the things happen to them and they are victims while others know that they create their experiences by understanding their own role and power to perceive.

2. Remember a confident guy who will bear his soul is a keeper

A guy who's not afraid to tell you what makes him emotional is probably above petty jealousy in relationships later on.

3. Beware of charisma as manipulation

Some people will say what they think you want to hear because they don't have enough faith in themselves to be authentic. If they're not honest with themselves, they won't be honest with you. Make sure your intuition and gut instincts are on alert.

More Great Ways To Get The Guy

You're on your way to more fulfilling connections with men.

  1. Some insights on the anxiety around "should I text him?"
  2. Find out where to meet men if you're coming up empty
  3. Don't hesitate to find out how to ask a guy out

In Conclusion

Gals, use these questions to ask a guy you like as inspiration and encouragement to go after what you want and bare your soul to the world.

The primary goal in questions to ask a guy you like is to learn everything you can about yourself so you walk the world with swagger and faith in yourself. These qualities alone will magnetize the perfect partner to you.

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