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83 Interesting Questions To Ask A Guy - The Best Way to Catch His Eye


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 24th, 2021

Heya – we have rounded up a mouthwatering collection of interesting questions to ask a guy just for you.

Let’s face it. First dates are horrible. They’re almost always tipsy job interviews - yuck. But it’s the first step towards opening up a door of possibilities for you. You could meet the man of your dreams or make a valuable connection.

A first date doesn’t have to be all doom and gloom. There’s way more to talk about than the cliché questions you have already backstalked anyway. Check out this collection of questions to ask a guy. You’ll love them.


11 Best Interesting Questions To Ask A Guy

So, you’ve had a crush on him for a while. He’s finally asked you out on a date. Only one problem… you haven’t the slightest clue what to ask a guy. Not only do you want to make an impression, you also want to know what he’s all about. We have a small manual for you. But make sure he doesn’t feel like he’s under a police investigation.

Here are the 11 best interesting questions to ask a guy:

1. If you are going to love someone, are you willing to give up even your love for yourself?

Do they think making sacrifices is a key part of loving someone?

2. Are you an emotional person or a practical person?

This will give you insight into how to deal with them.

3. Do you think all people deserve to be equal in all aspects?

This is bound to generate some debate.

4. DO you believe in magic?

Have fun with this one.

5. What was the most common impression you give to a stranger?

What misconceptions do people have about him? You may have your own, so chip in.

6. How would you like your girlfriend to be dressed up on the first date?

Tips for your next date.

7. Have you ever worn the same clothes consecutively?

Why on earth?

8. What do you think about your purpose in living?

What is their life mission?

9. Do you think money can buy the happiness of many people?

What's his attitude towards money?

10. If you could drink your entire life or eat your entire life, what would you choose?

A fun question to spark conversation.

11. Have you ever been caught lying?

Sshhhh... everyone has.

10 Engaging Questions To Ask A Guy To Get To Know Him

Looking to spice up the conversation on your next date?

Getting to know a guy takes more than the same old small talk questions. You need some help, and that’s why we’re here. Our list of interesting and engaging questions to ask a guy to get to know him is just what you need. These aren’t your normal run of the mill questions. They can get really deep.

Here are 10 interesting questions to ask a guy to get to know him:

12. If you wake up bald tomorrow, would you hide it or will walk out confidently?

Is he confident in his own skin?

13. If alcohol were banned, what would your reaction be?

Can he live without his favorite drink?

14. What talent do you wish you'd been born with?

Everyone has something they wish they could do.

15. Stupidest thing you ever did with your cell phone?

This can turn into a whole load of fun.

16. If your house is on fire what is the first thing that you will save?

What's his most valuable possession?

17. Does anyone know your computer ID password?

Find out of there's anybody in his life he trusts enough to share his password with.

18. What's the most spontaneous thing you've ever done?

Do they normally do stuff on a whim?

19. Can you cope with unexpected events?

Everyone deals with unexpected events differently.

20. What is the strangest excuse you have given to your boss for being late?

Don't shy away from telling him about yours.

21. What is the thing that will make you think I am bad?

What qualities does he hate in other people?

10 Appealing Questions To Ask A Guy You Like

You like him, huh?

But how exactly do you go from liking them to getting to know them? We have rounded up a collection of questions to ask a guy you like. Not only will they spark great conversation, they’ll also help you uncover their real personality. Enjoy, you can thank me later!

Here are 10 intersecting questions to ask a guy you like:

22. What is your view on church involvement?

This will spark a discussion on religious persuasions.

23. What gives you the most adrenaline?

What's that one thing that gets them excited?

24. What is a cause you're really passionate about?

What would they do even if they weren't getting paid?

25. What does your vision of a happy family look like?

Get their thoughts on the kind of family they'd want to have.

26. How often do you see your good friends?

Is friendship important to him?

27. How would you describe a good work ethic?

Everyone has an opinion on this.

28. If you were to make a YouTube channel, what would it be about?

This is something he loves doing.

29. How important is integrity to you? Why?

This question will help you learn a lot about them.

30. What’s your favorite song to dance to?

A fun guy should have a favorite song to dance to. Even if they're a horrible dancer.

31. What is the best thing about your personality?

What does he think is his strongest trait?

11 Fascinating Funny Questions To Ask A Guy

“After a while, you just want to be with someone who makes you laugh” -

Mr. Big (Sex and the City) had a point. Don’t just ask interesting questions. Make him laugh as well. After all, laughter does play a critical role in attraction. We have some interesting, funny questions to ask a guy that will get him to reveal more about himself and crack him up while at it.

Here are 11 interesting funny questions to ask a guy:

32. Have you ever laughed in a serious situation?

This should bring back some good memories.

33. If you could make anything free what it be?

This question always makes for good conversation.

34. What’s the dumbest trend to you?

This is bound to trigger some chuckles.

35. Have you ever been pranked?

You could talk about this for hours.

36. Are you a snorer?

Everyone has a funny opinion about snoring.

37. Do you like surprises?

Take notes...

38. Do you think time travel would be fun?

This is a great way to explore his wild imagination.

39. If you could splurge on one item, what would it be?

What's one expensive thing they wouldn't mind spending money on?

40. Have you ever won in a raffle?

The conversation can go in any direction.

41. Would you choose camping or an amusement park for a weekend getaway?

This can tell you a lot about their personality.

42. What was the best thing about your college experience?

Memories will come rushing back.

9 Compelling But Fun Questions To Ask A Guy

Picture this: you’ve finally found him – the man of your dreams. He’s tall, educated, successful, and is handsome enough to warrant a second or even third look. He’s hot. Hot enough to keep you feening for more. You want to make a great first impression. Here are some fun questions to ask a guy. He’ll be all googly eyed about you by the time you’re done.

Here are 9 interesting but fun questions to ask a guy:

43. What is your go-to drink on a night out?

You can't go wrong with this question.

44. What are your thoughts on pet names in a relationship?

Heated debate coming right up...

45. Have you ever used or would you consider using an online dating site?

You'll both have fun with this one.

46. Do you think psychic abilities exist?

Take a ride on the wild side.

47. What are your thoughts on who should make the first move in dating?

What are their thoughts about traditional gender roles?

48. Do you think that reincarnation is possible?

Everyone has an opinion about the afterlife.

49. Do you have any phobias?

Does he fear spiders?

50. When was the last time you were out of your comfort zone?

Do they push themselves to the limit?

51. If you could trade places with anyone who would you trade places with and why?

Who is the person they admire most?

15 Intriguing Random Questions To Ask A Guy

Asking questions is a great way to get to know a guy. But asking the wrong questions can make the whole experience feel like an interrogation. For this reason, you want to focus on questions that help develop the conversation. Our list of random questions to ask a guy is just what the doctor ordered.

Here are 15 interesting random questions to ask a guy:

52. Do you believe it is possible to have lived a previous life?

One of life's most puzzling questions.

53. Can you tap dance?

A conversation about dancing can't possibly go wrong.

54. If you had friends around what DVDs would you have to watch?

What do he and his friends have in common?

55. Have you ever needed stitches?

Have them recount a horrible experience they had. All dudes have had one of these.

56. What do you consider is the most important piece of furniture in a house?

Do they have a favorite spot in the house?

57. How often do you wash your ears?

Weird. But it could turn into an interesting conversation about hygiene.

58. Have you ever started a rumor?

You can't go wrong with this question.

59. Have you ever felt like you lost a promotion or job that you really wanted to someone who was less qualified than you?

That's everyone...

60. Have you ever slapped someone in public?


61. Have you ever flown first class?

Always a good experience to talk about.

62. What's your favorite biscuit to dunk?

Who doesn't love to dunk a biscuit?

63. How many remote controls do you have in your house?

This should make them smile.

64. What are your most important rules when going on a date?

Everyone loves to talk about dates.

65. Have you ever had anything published?

Great question for a writer.

66. Do you like your name?

Do they hate their name? Do they love it? Why?

17 Deep Enticing Questions To Ask A Guy

Newsflash – a guy would rather endure a rerun of Housewives than reveal their deepest feelings. You like to talk about your feelings; he doesn’t. It’s not his fault. That’s just how he’s wired. We have some deep questions to ask a guy that is bound to get those lips moving.

 Here are 17 interesting deep questions to ask a guy:

67. Do you think love letters are overrated?

Has he ever written one?

68. What’s the thing you most want to do with your life?

Do they have life goals?

69. Do you have a list of things to do before your ‘x’ years old?

Is it possible that you share some goals?

70. Do you think life is fair?

He can talk for hours about this.

71. Do you sometimes feel you have the need to shout?

Have them explain their reasons.

72. If you discovered a new species of dinosaur what would you call it?

This should be fun.

73. Is there a feeling you are trying to ignore?

Are they good at expressing their feelings?

74. How important is a commitment to you?

This is a great question if you're looking to get into a relationship with him.

75. Have you ever had a dream you chased only to be let down when you achieved it?

Have they met disappointments and how did they deal with them?

76. Do you think your parents are happy with the person I have become?

This says a lot about his relationship with his parents.

77. What do you think is a good age to have your first child?

It's okay to find out when they plan to have kids if you're looking to build a future with them.

78. What do you remember to be the worst day you’ve ever had?

Every dog has its day.

79. What do you think is a more valuable donation, money, or time?

There's no right answer to this one.

80. Have you ever felt like you met someone in a previous life?

Stranger than fiction.

81. Do you mind getting famous even if it’s from bad publicity?

What's their take on fame?

82. Are you concerned with saving the earth for future generations?

This is a great question for a guy who cares about the environment.

83. Would you rather the world remain peaceful forever or no one on earth ever goes hungry?

Tough choice. But it will make for great conversation.

Downloadable and Printable List of Interesting Questions to Ask a Guy

Here is a downloadable and printable List of Interesting Questions to Ask a Guy (right click image and select Save Image As...):

How To Pick The Best interesting Questions To Ask A Guy

Going on a date with a guy? The questions you ask him will make or break the interaction. You don’t want to wing it. Prepare. Here’s how to go about picking the best interesting questions to ask a guy.

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

1. Make Preparations Ahead of Time

You want to start making preparations as soon as you’ve confirmed the date. This will allow you time to pick questions that you think will resonate with the guy and keep the conversation going. Being prepared helps temper the nerves during the date.

2. Avoid Yes-No Answers

You’ll want to avoid questions that will elicit a no or yes answer. Open-ended questions work best when you’re trying to engage a guy. You’ll avoid awkward moments where you have nothing to say after they’ve answered a question. If you ask a yes or no question, be prepared with a follow-up question.

3. Incorporate Humor into The Questions

A date is not an interview. You should ask questions with a light-hearted, humorous tone. Throw in a joke now and then to keep things interesting.

4. Get Some Inspiration

You don’t have to come up with an original set of questions to ask a guy. Choose a few questions from our massive collection. Warning – they’ll work a treat.

More Great Ways To Talk to Guys

Find it challenging talking to guys? Your fear is irrational. It’s quite easy to get a conversation going with a guy. We have a lot more tips to help you get acquainted with the guy of your dreams.

    1. Fancy him? We have some tips on how to ask a guy out that will work like a charm.
  1. The first impression is always the most important. Here’s how to start a conversation with a guy without looking like an idiot.
  2. Should I text him? Is it too soon? What should I say? We have the answers to all these questions and more.

In Conclusion

One of the easiest hacks for success when dating is to have the right questions to ask a guy. Our collection of interesting questions will help turn a dull date into a fun, memorable one. Give them a try.

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