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

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.

Let's start.


10 Best Questions To Ask A Guy You Like

A flirty question or a dirty question is not ideal if you want to get to know a man deeper. The best questions to ask a guy you like are those that will make him think and reflect on himself.

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 deep 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?

What's your favorite movie? Is your celebrity crush there? Kidding aside, 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? This is the right question to ask to know if he's able to live freely without the internet.

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

Doing stupid things in public is my biggest pet peeve. Regardless, humility and humbleness, and the 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? I don't know about you, but this question is the nicest thing to ask a person you want to know.

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.

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 by asking about his favorite food. Talk about preparing for the future!

13. What is your staple party dish?

Is it chips and salsa or more refined pigs in a blanket? Believe it or not, serving unappetizing food at parties is a lot of people's biggest fear.

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

This is a great question to ask someone you like if you really want to know more about them. We cement our core values often because they are indirect, abrasive contrast with those of our parents. Who knows? This may ignite a favorite memory.

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. Perhaps the biggest turn of your conversation would be a talk about getting your dream job abroad.

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. Moving away from small talk with a topic like this makes for an interesting conversation.

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. You'll know that a mundane experience and a fun thing are not always different things.

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?

Drop the awkward silence and dive into topics like this- no dirty talk too! Truth be told, 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. Asking him this can open up a great conversation rather than only asking about his favorite song, favorite sport, or favorite book.

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.

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

Ask this funny question to 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. This interesting question will tell you if he's an excellent companion to shops with freebies.

27. Which TV family is most like your own?

Metaphors are fast-track ways to get tons of information. This might come off as a personal question, but it can reveal plenty of things.

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

Asking questions like this lets you know a lot of information about the other person. 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? This random question will pave your way to new topics.

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

This conversation starter surely is interesting enough. 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? Plot twists like these are my favorite thing in reading a book. However, the story would be different as it happens to you in real life.

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

This good question can open up a dialogue about which house gadget is the best. 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?

What's the worst thing or the funniest thing that could happen at night? A ghost tearing off your legs or you know, for oxygen... This conversation topic will point you at something both of you believe in.

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. Amazing questions like these can trigger conversations about the craziest thing ever.

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? Is it your biggest regret?

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.

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 signs 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 boy 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.

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 man 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 a while and you'll need some deeply personal questions to ask a guy if you are to truly discover compatibility and gain your own self-awareness in the process.

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 were 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 a 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 beau immediately at first encounter and far into your relationship with these personal and deep questions to ask.

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

We hope for a man 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.

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

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. Opening a conversation with this one can give you the better idea of what he likes in a woman.

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 in 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 boy remains interested, especially if you choose fun questions to ask a guy.

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 when you ask this fun question.

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 in a conversation.

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 cute question.

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! This conversation starter is an excellent way to know what he'd do with power.

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 man 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 boy you like (right-click the image and select Save Image As…):


There's nothing wrong with looking up ways to catch a guy.

What's the craziest thing to ask?


What is the most awkward question to ask?

What are some juicy questions?

How do I know if I'm asking the right question?

How to impress your crush?

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

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

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 person 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 bear 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.