Do you need a good list of interesting questions to ask a guy? We've got it here for you.

I've written many articles about the right questions to ask a guy that will get him talking for hours. That's why I know that this list is exactly what you need to help you talk to guys and make them feel comfortable around you.

Let's get started!



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.

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? If so, a deep question like this will help you know more about how much they prioritize the people they love. You can even ask if they have ever done something like it. People tend to disregard personal needs when they are invested in a person they love. See what kind of things they have done to show how much love they have for someone.

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

This is the right question to ask if you want to know them even deeper. Don't be afraid to ask personal questions like this because he will think that you are really interested to know him. Plus, this a good question to ask if you'd like to check your compatibility with that person. If you're worried about repeating mistakes from a past relationship, it's great to know stuff like this before it gets too serious.

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

This interesting question is bound to generate some debate. Make sure you keep an open mind when you get an answer you don't like. You could also provide your perspective, but it's important to remember that you're asking this to find  out if you share the same ideas. If you hear something you don't like, be open to the idea and maybe you can see the premise from another angle.

4. DO you believe in magic?

Whats one thing you've always wanted to do if you had magic powers? He might have a lot of good answers about magic and the unknown. It will tell you if he's imaginative and open-minded to things that can't be explained. It's not exactly a funny question, but it will help you get the ball rolling and talk about fun and whimsical things.

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. He may even share a related story about people's impressions of him, so it's definitely a great question to talk about. You'll learn what people initially think about him and see if it matches your impression of him as well.

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

This is one of the flirty questions you can ask a guy you want to date. Whatever he answers, you can use this as a guide for your next date. If he likes girls dressed simple for a date, then that's your cue. It's time to bring out a nice pair of jeans and a fun blouse to your next date. If he likes confidently dressed women, get your coordinates out and a powerful pair of heels. He'll swoon, I swear.

7. Have you ever worn the same clothes consecutively?

First of all, does it mean you have not showered? Because I think this question has more to do with hygiene than fashion choices. Pay attention to how he answers this personal question because you have to be willing to put up with his hygiene practices if you want to date him.

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

This is one of the deeper questions you can ask a guy if you want to know him to the core. One's life purpose is necessary because that's what eventually keeps you going. It can be discovered in a hobby or even your dream job, but it may as well be the hardest thing to figure out in your life. What's certain is that you'll be able to have a meaningful conversation out of this interesting question.

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

Good questions like this will tell you a lot about a person. It will show you his attitude about money and what kinds of things he prioritizes. There are things that money can buy that grants people peace and security. However, if that will be the basis for happiness for him, then it's time for you to figure out if you agree with it.

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

This could spark a great conversation about your favorite food or drinks. If you want to make a good impression, you should take note of the stuff he says and bring some of them for him on your next date. He will then think that you're actually listening to him. He'll also appreciate that you went out of your way to bring him the stuff he likes.

11. Have you ever been caught lying?

Get him to tell you about one of the times he was caught lying. It might even be his favorite memory as a child. Ask him to think of the funniest thing he lied about and share some of your funny lying moments as well. See how he works his way out of the lies he told so you can tell if he becomes a little shady in the future.

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.

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

Is he confident in his own skin? In a healthy relationship, you have to be willing to accept each other no matter what physical changes you go through as you age. If you can't accept yourself, how will you do the same for your partner? That's why this is a good question to talk about. You should know how he handles change.

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

Can he live without his favorite drink? If his favorite thing to do at the end of the day is to relax with a few beers, see what he'd do if he didn't have that luxury. For some men, it might be the craziest thing for them to go through a day without a beer. So, see what other activities or routines he'd enjoy instead of the usual drink at the end of the day. You might discover that he's more fun without alcohol.

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

Everyone has something they wish they could do. Now, the talent they want is probably an embarrassing thing for them to admit. However, be open to his answers because he might share something he's insecure about. You can even share your secret desire of wanting to read people's minds and being able to fly.

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

This can turn into a whole load of fun. Let's find out the stupidest and worst thing he's ever done with his phone. You will be surprised with questions like this, because you might get weird and funny answers that you never expected out of him. You can turn this into a dare question and ask him to do it again. Did he send an inappropriate text to his boss? Did he send a sexy photo to his mom? Challenge him and find out.

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

What's his most valuable possession? If he's into action figures and superheroes, he might save some of the most valuable pieces of his collection. Granted, it might be a fictional character, but it might have sentimental value to him. That's where you dig for a deep conversation. Let him talk about why it's the first thing he'll save. Then, ask more follow-up questions so he'll be comfortable sharing more with you.

17. Does anyone know your computer ID password?

Find out if there's anybody in his life he trusts enough to share his password with. If he shares that his ex-girlfriends had access to his password, then you'll know that it is something he'll be open to in the future. Ask him to share his experience and whether or not he's good with doing that again in the future. It's important that you know this because if you want to do this with him, you should already know if he's okay with it.

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

Do they normally do stuff on a whim? Get ready, because you might hear the funniest thing he's ever experienced. Once he's shared the most spontaneous thing he's done, you should also tell him some moments where you felt like doing something just for fun. Show him how open you are to different experiences because he might like you even more if he sees that you know how to relax and have fun.

19. Can you cope with unexpected events?

Everyone deals with unexpected events differently. You can ask him to share a time in his life when he had to face something completely out of the blue. Then, listen carefully to how he handles things under pressure. It will show you if he knows what to do in the face of challenges. You can also share how you cope with unexpected events and impress him with being graceful under pressure.

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

Everyone's probably thought of some excuse for being late. When you do it often, you have to think of more creative ideas to make it believable. Whether he said he hit a goat on the way to work, or that he had to pick up his grandmother from yoga, it will be a fun conversation to have you're going to know how he gets out of sticky situations.

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

What qualities does he hate in other people? Do you have those qualities? It's important for you to know the things that turn him off and find out if you are willing to bend over backwards to change yourself according to his preferences. It's good for you if you fit into his standards of a good person. But if there are some of your qualities that you know he doesn't like, are you okay with changing? Ask him and find out for yourself.

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!

22. What is your view on church involvement?

This will spark a discussion on religious persuasions. Is he particularly spiritual? Stuff like this are relationship questions you need to settle before you get a little too serious. Talk about differing beliefs and spiritual tendencies and see if you can come to a common ground. Before talking about marriage and babies, you first have to see if you respect each other enough to accept varying perspectives.

23. What gives you the most adrenaline?

What's that one thing that gets them excited? Maybe it's meeting their childhood celebrity crush or going cliff-diving in the ocean. Some women love it when men are adventurous and spontaneous, so find out if he fits into your definition of adventure. If he turns out to be a little too boring for you, it's good to find out early on.

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

What would they do even if they weren't getting paid? Once you find out what he's passionate about, that's your chance to bond with him. If you want to get closer to him, offer to come with him to a class or watch him do that specific thing. Let's say he likes painting. Set up a date to go to a painting class or find a good museum nearby to stroll around. He'll appreciate your effort to connect with him by doing the things he likes.

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

This is an important thing to ask because you'd want to know what they envision as a happy family. If you're serious about each other, you're probably already planning your future together. You should talk about what kind of family you'd like. Do you both of you want kids? Where should you live, in the city or the suburbs? Will you both of you work or will one of you stay at home to take care of the kids? These are essential things to discuss before you take it to the next level.

26. How often do you see your good friends?

Is friendship important to him? You'll know from his answer. If you're going to be in a romantic relationship with someone, you're going to learn about his platonic relationships too. How much does he value them? Does it look like he puts them first all the time? Before you get serious, you should know if you're comfortable enough with the relationship he has with his friends.

27. How would you describe a good work ethic?

Everyone has an opinion on this. You should know what he thinks is a good work ethic and see if you're comfortable with that. If his job is very demanding and he sees that working overtime and on weekends is a good work practice, it's best for you to know beforehand for you to gauge if you're good with it.

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

This is a fun conversation starter when you want to get to know someone's interests. He will probably answer with something he really likes to do. If he answers something specific, like cooking or DIY home projects, take that as a cue to do those stuff with him. You don't have to be as good as he is, but you should show that you're interested to see what he loves about them. You'll see a different and deeper side to him when he shows you his passions.

29. How important is integrity to you? Why?

This question will help you learn a lot about them and their values. Does he feel like he can be honest with you? Does he feel strongly about openness in a relationship? Find out if his standard for integrity matches yours. That way, you will know how open he can actually be with you if you decide to get serious with him.

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. Whether it's a classic dance song or a high school bop, there will always be a song that gets them going. Find out what his favorite is and play it at random times when you're together. It will instantly put a smile on his face when he sees that you remembered his song.

31. What is the best thing about your personality?

What does he think is his strongest trait? When he reveals this to you, you'll know that it's the thing he's most proud of. It can be his loyalty to his family, his great sense of humor, or even his love for his pets. Pay attention to what he says and look closely when he shows off this trait. He's going to be showing a side that not a lot of people may know.

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.

32. Have you ever laughed in a serious situation?

This should bring back some good memories. Sometimes it's so stifling to be in an intense moment that you'd do anything to defuse the tension. And sometimes, without even knowing, you might let out an involuntary laugh. Ask him if he's ever done that and what kind of situation he was in. This will tell you what kind of situation he feels uncomfortable in.

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

This question always makes for good conversation. His answer would probably be something he absolutely loves that he'd never get tired of. Maybe it could be his favorite food or his favorite brand of shoes. You'll get to know some of his likes and you can take notes when you want to get him a gift in the future.

34. What’s the dumbest trend to you?

This is bound to trigger some chuckles. Your conversation partner will love talking about this because there are so many trends that pop up on the Internet every few weeks. Whether it's planking or dancing on Tiktok, you can talk endlessly about these trends and the people you know who actually did them. He could have also done some of these trends, so maybe you can get him to fess up.

35. Have you ever been pranked?

This is one of the best conversation starters we have here. Being pranked could be one of the most embarrassing moments of someone's life. Ask him if he's been pranked before and how he handled it after. This will tell you how classy he is in the face of adversity. Let's see if he can be the bigger person in any situation.

36. Are you a snorer?

Everyone has a funny opinion about snoring. Also, it would be a good thing for you to know before you sleep together because you'd want to be prepared if he snores really loudly. You can also figure out for yourself if you can handle someone who snores. And, you can share if you also do the same.

37. Do you like surprises?

This is a flirty question that will tell you a lot about what stuff he likes. If he enjoys surprises, then that's your cue to plan something unexpected for him. You can make him his favorite meal and have it delivered to his office on a random day. You can plan a weekend getaway with him and surprise him with his favorite outdoor activity like hiking or biking on a new trail. He'll love that you planned something for him.

38. Do you think time travel would be fun?

This is a great way to explore his wild imagination. Ask him if he also has any regrets that he would like to change if he could go back in time. You'll see how comfortable he is to share what he wants to change about the past and how open he is to talk about the stuff he's done.

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

What's one expensive thing they wouldn't mind spending money on? This is a fun question to ask because you'll get to know what stuff he considers to be a luxury. Pay attention to the stuff he says and take notes for the next time you want to get him a gift for a special occasion.

40. Have you ever won in a raffle?

This random question can make the conversation can go in any direction. Ask him how often he joins in raffles and if he's ever won one. And if he has, ask what he did with the prize. Did he keep it? Did he give it away? Did he sell it? It's a great topic for conversation that will keep you busy for hours.

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

This can tell you a lot about their personality. Are they into thrilling activities? Or do they enjoy the wild outdoors? Either of these choices will give you a hint of what they'd prefer if you were to plan something for both of you. You'll know which to pick the next time you need a weekend away.

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

This question opens up a lot of other topics related to college. Ask them what their favorite place was to study when they were in college. You can also ask dare questions like, "What was the weirdest thing you did when studying for a big test and can you show it to me now?" Talking about college is going to expand the conversation very well.

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.

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

You should know the answer to this question if you're planning to be together long-term. That's why you should be asking important questions like this so you become the best girl for him. Knowing his go-to drink, his fast food order, or even his brand of shaving cream are just some of the things you need for him to fall head over heels for you.

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

There are some people who like it and some people who despise it. Either way, it would be good for you to know his thoughts so you don't accidentally call him "Baby" or "Sweetheart" and have him cringe and make a face. At least you'll know what he prefers. You could also share your preference, in case he wants to call you a pet name too.

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

You'll both have fun with this one. Online dating used to be so taboo, but nowadays it's becoming a trend. Many people find their long-term partners online and they often share their stories to encourage people to try it out. Find out if he's ever used it or if he's open to using it to find his soulmate. Pay attention as he might say he's already on a dating site... then you might want to keep your options open too.

46. Do you think psychic abilities exist?

This is actually just a question to see if he keeps an open mind. Not many people believe in this kind of stuff, so it would be fun to find out if he does. You can also open up the conversation to many other unusual things that he might believe in. Does he think aliens exist? Is he a fan of astrology? When you ask him these, be prepared with a big jug of water because you're going to be talking all night.

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

What are their thoughts about traditional gender roles? In this day and age, more couples are steering away from society's expectations of what a man and a woman should do. That's why when it comes to dating, making the first move might not matter as much as it did. Let him discuss what he thinks about this and about gender roles in dating. Be careful though, as this might stir up a debate.

48. Do you think that reincarnation is possible?

Everyone has an opinion about the afterlife. Find out what he believes in and allow him to explain why he believes that to be true. No matter how different your views are, it's great to listen to each other and get to know a person from their core beliefs. If he feels strongly about this, you will see a side of him that he might not share with everyone.

49. Do you have any phobias?

Does he fear spiders? Is he afraid of heights? Does he freak out when he's in an enclosed space? These are only few of the most popular phobias known to man. If there's anything he fears, you should know them and do what you can to keep them from him.

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

Do they push themselves to the limit? Ask them to share a time where they had to go out of their comfort zone and do something they never expected to do. This will reveal how they respond to unexpected circumstances and you will learn what situations they're not exactly used to.

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

Who is the person he admires most? This might be the person he'd trade places with. Ask him to explain the things that person has that they want. Do they have a good family? Are they rich? Do they lead a good life? Let him tell you the things he wants in life and find out if they align with yours.

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.

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

This is one of life's most puzzling questions. The concept of past lives doesn't seem that outrageous to some people. We have all stopped and realized we were having de ja vu. Ask him if he thinks he's lived a past life and get him talking about what kind of person he must be back then. It will let him get into the specifics of what other jobs he could have taken or what other paths he considered if he had another life.

53. Can you tap dance?

A conversation about dancing can't possibly go wrong. Whether he answers yes or no, ask him to try and demonstrate it for you. I guarantee he'll be asking you to dance with him. It's a great way to ask him to dance without actually having to ask him.

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

What do he and his friends have in common? Do they enjoy the same genre of films? Find out what kind of movies he likes to watch and schedule a movie night with him to watch one of them. He's going to love that you are willing to try the stuff he likes and that might make him like you even more.

55. Have you ever needed stitches?

Have them recount a horrible experience they had. All dudes have had one of these. You will know from his reaction if it's a funny or a traumatic memory. If he laughs, you can ask a follow up question and let him talk about what made it so funny. If his smile turns into a straight face, it's best to talk about another topic.

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

Do they have a favorite spot in the house? That will most likely have his favorite piece of furniture. Does he lik

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.

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.