Are you looking for questions to ask a guy to get to know him?

Wild guess: You’re here because you met a guy you kinda like.

You said hi.

He said hi back.

And then… the dreaded awkward silence.

Hoo boy! Not a great start, huh? Now he thinks you’re a weirdo.

No biggie. On to the next one, right? I mean...I’m sure it could have been worse. You could have hit him over the head and dragged him home. That wouldn’t look good on your rap sheet.

But here’s the thing - It doesn’t have to be this way. You see, getting to know someone isn’t rocket science. You don’t have to jump through hoops. You just need to know the right questions to ask a guy. You’ll get the lowdown on who he really is.

Today, we have some handy tips on how to start a conversation with a guy. You’re gonna love our sneaky get-to-know-him tips.


20 Best Questions To Ask A Guy To Get To Know Him

Want to get to know a guy?

The only true sign of success is feeling like you genuinely connected with him. The best way to go about it is to ask the right questions – beyond the go-to “what are your hobbies?” Today, we have some quick questions to help bring you closer.

1. What are your hobbies, and how did you get into them?

Find out what they're passionate about.

2. Who do you most like spending time with and why?

Would they rather hang out with their family or friends?

3. Do you like going to movies or prefer watching at home?

Great way to find out whether they’re an introvert or extrovert.

4. Do you ever wish you were raised differently?

Find out about his relationship with his parents.

5. What's one thing that can instantly make your day better?

Find out what cheers them up

6. Ideally, how would you spend your birthday?

Take notes. If you end up together, you’ll want to remember this.

7. How do you feel about family events?

Do they have a tightly knit family?

8. Is there any product that you couldn't live without?

This could make for great conversation.

9. Which family member do you confide in most?

Who do they consider closest in their family

10. What’s the career highlight you’re most proud of?

Are they career driven?

11. What’s your philosophy in life?

What drives him?

12. Are you more of a "work to live" or a "live to work" type of person?

Understanding why they do what they do can help develop a strong bond.

13. Are you religious or spiritual?

If you're religious yourself, then you might feel connected to someone who has the same beliefs.

14. What originally got you interested in your current field of work?

This is bound to lead to hours of interesting conversation with a guy, especially if they're passionate about their work.

15. What’s something you can’t go a day without doing?

Spark conversation with this gem.

16. Do you consider yourself good at networking?

Find out how good they are with people.

17. Do you have a professional mentor? If not, do you want one?

Having a mentor is a sign that they take their career seriously.

18. What is the greatest struggle you’ve overcome?

Are they a fighter or a quitter. make sure to share your own.

19. What was your longest relationship?

Is he a keeper?

20. Who is your favorite historical figure?

take a trip down memory lane with this one.

20 Questions To Ask A Guy You Like To Get To Know Him

You like him. And you’re hoping the feeling is mutual.

You’re also hoping that he’s your kind of guy. And you want to know him, even make him slightly obsessed with you. Bust out these questions to ask a guy you like and he won’t stand a chance.

21. What’s the first question most people ask you when you meet?

This will make for great conversation.

22. Dogs or Cats?

Everyone has a favorite, or two.

23. Where do you usually get your news?

An opportunity to talk about current affairs.

24. How can someone win a gold star with you?

Find out the qualities they look out for

25. What’s closest you’ve ever come to being arrested?

This should elicit some laughter.

26. What kind of parent do you think you will be?

Do they want kids in the future?

27. What’s one thing you wish you knew how to do?

This is a great conversation starter.

28. Do you prefer giving chocolate or flowers?

Cough cough... a fishing expedition, perhaps?

29. What was the last book you read? And When?

Maybe you share some favorite reads.

30. What are your hobbies that you like to do alone?

Maybe you could join him.

31. What is your biggest irrational fear?

Have fun with this one.

32. Do you enjoy small talk with strangers, or do you try to avoid it at all costs?

Great way to uncover their personality.

33. What song makes you unconditionally sad?

Everyone has that one song.

34. Have you ever tried a fad diet craze?

This could be interesting.

35. What is something that you find unsettling?

What makes their skin crawl?

36. Are you spontaneous or a planner?

Are you two peas in a pod or do you complement each other.

37. Have you always had the same political beliefs?

This is a sneaky way to get them to talk about their political persuasions.

38. What are you completely bored with in life?

What's that thing that turns them off?

39. Have you ever cried tears of joy?

This will cheer up any conversation.

40. If you could have a superpower what would it be?

Always works a treat.

20 Fun Questions To Ask A Guy To Get To Know Him

Boring conversations - they happen.

You don’t want to bore a guy to death asking dull-as-dishwater questions. Our collection of fun questions to ask a guy are so hot you’ll use them again and again.

41. What kind of car did you wish you had when you were a kid?

Every man loves to talk about their dream car.

42. What do you think is the hardest part about raising children?

What's the one reason they wouldn't have children.

43. What's a movie you can practically quote from start to finish?

Movies always make for a great conversation topic.

44. What do you do when you’re not working?

A chance to both share your hobbies.

45. How would you describe your sense of humor?

This one should yield an interesting answer.

46. Do you like to sing karaoke?

You hope he does.

47. When was the time you felt most free?

This question will give you some insight into who they really are.

48. Where is the last place you traveled to?

Find out if they're adventurous.

49. Have you ever eaten so much that you had to relax afterward?

Ha ha ha... yes.

50. If you got engaged, how long would you want to wait before getting married?

Are you compatible?

51. If you could take out a bad day on a household item, what would you choose?

This should be interesting...

52. If you could choose how it would happen, how would you want to die?

This question should help you understand how they perceive life and death.

53. Who would you want with you if you were stranded on a deserted island?

Who's that one person they trust with their life.

54. Do you prefer to dress up or dress down?

Do they have a fashion sense?

55. Where do you most want to travel, but have never been?

Everyone has a dream destination.

56. What is your worst weather experience?

The weather always makes for great conversations.

57. Who do you look up to and why?

people tend to mirror the people they admire.

58. How many times did you have to take your driving test?

Failing a driving test is just part of life.

59. What’s a story of yours that you don’t get to tell often enough?

You might just uncover a great story with this one.

60. What is your dream home like?

What kind of life do they aspire to live. A home encapsulates a man's life.

5 Funny Questions To Ask A Guy To Get To Know Him

Fun fact: One of the best ways to keep a conversation alive and interactive is to ask questions.

The icing on the cake is to make the questions funny. This will not only give you a gateway to his mind, but also his heart. With our collection of funny questions to ask a guyyou’re all set for a delightful conversation.

61. How long do you take to get ready to go to work?

This is a fun question that always gets interesting answers.

62. What is a saying or expression that you probably say too much?

You've probably picked it out already.

63. Do you untie your shoes when you take them off?


64. Are pets better than humans?

Most people will answer in the affirmative.

65. What color dominates your wardrobe?

Sneaky way to find out what their favorite color is.

14 Flirty Questions To Ask A Guy To Get To Know Him

Hoping to spark things up with? Get flirty.

Flirting always seems easy in theory. But when you’re caught up in your thoughts during a date, your best-laid plans go out the window. Luckily, we have your back. We’ve compiled a mouthwatering list of flirty questions to ask a guy. He’ll be eating out of your hand by the time you’re done.

66. How do you deal with heartbreak?

Everybody has a unique way of dealing with heartache.

67. How old were you when you had your first kiss?

That first awkward kiss is always the most memorable.

68. Do you believe that couples should wait long before getting married?

This is one of those different strokes for different folk issues.

69. What is the stupidest thing for a couple to fight about?

Something to laugh about.

70. Have you ever been with someone who is too manipulative/controlling?

There's always that one wack job.

71. What age do you plan on settling down?

Are your future plans in sync?

72. Do you think children are necessary to make a marriage complete?

What's their take on having children.

73. What is something you know you do differently than most people?

What makes them uniquely them?

74. What traditional gender roles do you agree with?

This is bound to become a heated debate.

75. What does it mean to" be a man" in today's society?

Get a glimpse into what he thinks his role in society is.

76. How do you know when you have had too much?

Do they have the presence of mind to know when they get to their limits?

77. What makes you feel safe?

This question will shed some light on his insecurities.

78. What is the most dangerous thing you have done to impress someone?

Do they have an appetite for risk.

79. What makes you jealous?

Everybody encounters the green-eyed monster.

5 Interesting Questions To Ask A Guy To Get To Know Him

Here’s the thing… a guy is not going to stick around unless you’re interesting. But how exactly do you do this? How can you “be interesting”?

We have a hack. Ask interesting questions. Everything else will flow from there. We have compiled a list of interesting questions to ask a guy so you never have to worry about what to say ever again.

80. What goal are you working on now?

Find out if they're goal oriented.

81. What’s one item you want to own that you don’t?

This can take a conversation places.

82. If you could only remember one lesson to take into your next life, what would it be?

What's the one thing they've learned that has had the biggest impact on their life?

83. How do you like to spend a rainy day?

Sounds silly... but it always gets an interesting answer.

84. What is your go-to outfit?

What's his style?

5 Random Questions To Ask A Guy To Get To Know Him

Looking to strike off a lighthearted conversation with a guy so you can get to know him? You really like him but don’t know how to start a conversation or what questions to ask. Maybe you’re just a little shy and need a little help. Hurry up to apply our collection of random questions to ask a guy.

85. What law do you think makes no sense?

A great way to pick his brains.

86. Do you like politics?

Everyone is a politician. They just don't know it.

87. When was the last time you did volunteer work?

Do they help the less fortunate in their free time?

88. What are you most likely very wrong about?

This question will bring to light their level of self awareness.

89. If you were a teacher, what subject would you teach?

You'll find out what they think they're really good at.

5 Personal Questions To Ask A Guy To Get To Know Him

Girls… you’d be surprised to discover how many men are insecure about answering personal questions. But there’s no point in having a relationship with someone without really knowing them. We have some personal questions to ask a guy to get him to open up.

90. What have you created that you are most proud of?

This will help bring out his creativity and passion.

91. How do you compartmentalize your life?

This question can easily lead to hours of conversation.

92. What’s the most impactful ‘no’ you’ve said recently?

Does he have strong boundaries?

93. At what point did your life change for the better?

A classic question that gives you insight into their personality without being too invasive.

5 Deep Questions To Ask A Guy To Get To Know Him

Wanna take your relationship with a guy to a deeper level? I know… it’s a tricky task. This is especially so if he’s cagey like most men. We’ve put together a list of deep questions to ask a guy just for you. Careful, some of these might be a bit too serious, so choose wisely.

94. What is the basis of your standard of right and wrong?

This question will delve into his moral compass.

95. What mistake do you keep making again and again?

Find out what their biggest weakness is.

96. Do you find it hard to say sorry?

Learning to say sorry is divine. It can make or break a relationship.

97. If past lives were real, what were you?

What would they be if they were not who they are now.

98. How do you balance your personal life and career?

This question always gets a response.

5 Questions To Ask A Guy Over Text To Get To Know Him

If you’re just getting to know a guy for the first time, you’re probably going to need to figure out what questions to ask a guy over text first.

99. How do you normally deal with stress?

His answer will share a lot about his personality. When you get his answer, you’ll learn whether he deals with stress in a constructive manner.

100. Are you a competitive person?

Almost every guy will answer “yes,” but he’ll also reveal key details about how he competes. This is all important info.

101. Can you honestly say you love what you do every day?

Just a heads up - not many people actually can say yes to this question. However, he’ll probably let you know about his dreams if the answer is no.

102. How long can you hold a grudge against somebody?

This is another really illuminating question, and you’ll basically get a sense of whether or not he’s over his ex.

103. What are you thinking about at night when you can’t sleep?

Even though you’re chatting over text, there’s no reason you can’t ask deep psychological questions like these. In fact, sometimes guys are more willing to answer over text.

How To Pick The Best Questions To Ask A Guy To Get To Know Him

So many questions and so little time…

You’re right. It is kinda overwhelming. The thing is, you need to narrow down your options to just a few questions. But how exactly do you do this? Let’s break it down.

1. Identify Characteristics of the Kind of Guy You Like

Start by identifying the qualities you love in a guy. For example, you might want a charming guy, a go-getter, funny, and other characteristics. Making this list helps you get some clarity on the kind of guy you want. You won’t waste time chasing the wrong guys.

2. Come Up with Questions That Help Bring Out the Characteristics You Identified

Now to find out if the guy has the qualities you desire

It’s unrealistic to expect a guy to meet all your expectations, but they should at the very least meet some basic ones. Figure out how you’ll weave these qualities into your questions. For example, you can use the funny questions on our list to make him open up.

3. Determine What Questions to Ask Before Meeting Up with Them

First dates can be incredibly nerve-wracking. You want to have an iron-clad set of questions that you can ask even when the first-date butterflies morph into Mothra. Narrow down your options to a few questions that you can easily remember.

Downloadable and Printable List of Questions To Ask A Guy To Get To Know Him

Here is a downloadable List of Questions to Ask A Guy To Get To Know Him (right click the image and select Save Image As...):

More Great Ways To Talk to Guys

Loved our tips on getting to know him? We have more tips to help you score the man of your dreams.

  1. You have to start off by meeting him. Here’s a guide on where to meet men.
  2. The next step is to turn on the sass in you. Here some timely tips on how to flirt with a guy. He’ll turn to butter in your hands.
  3. Should I text him? How soon is too soon? We also have this covered.

In Conclusion

Dating is an intricate dance where you learn about each other. These questions to ask a guy to get to know him can help make the process much easier. As you master the questions to ask a guy, you’ll also learn how to start a conversation with a guy.