Sam Whittaker | Jun 13, 2022 | 0
110 Good Questions to Ask a Guy - Start a conversation with your bros!
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Everyone should know some good questions to ask a guy.
And if you’re reading this article, you know that’s not always as easy as it seems. Everywhere you look there are posts with questions to ask a girl, but finding a list of good questions to ask guys is much more difficult.
So, to help you out, I’ve put together a list of the best questions to ask a guy that are sure to help you.
Whether you want to make new friends at the gym or develop your relationships with the fellas at work, asking good questions shows your interest in the other person and is shown to increase people’s positive feelings toward you.
Keep these questions to ask a boy, close at hand and you‘ll find the Starsky to your Hutch in no time.
18 Best Questions To Ask A Guy
Conversations are the lifeblood of any good friendship.
They are the means by which we get to know one another and encourage, comfort, and challenge each other. Great conversations don’t just happen, however. Sometimes a few conversation starters are needed to kick things off before the conversation can take on a life of its own.
These questions are the best conversation starters I’ve come across, and if they can work for me they can work for anyone.
Here are the 18 best questions to ask a guy:
1. What is the most interesting piece of trivia you know?
You never know when that useless information will be useful.
2. Which historical figure wasn’t as amazing as most people think they were?
History is filled with controversial figures. Which one does he think is overrated?
3. What’s something you were really stressed about, but turned out to be no big deal?
Stress can be paralyzing, but it doesn’t always have to be.
4. What would you NOT do for 5 million dollars?
There’s probably a lot he would do, but where does he draw the line?
5. What’s your worst customer service story?
Either as the customer or the employee, we’ve all had bad experiences.
6. If you could become the number one expert in one niche field, what would it be?
Midnight quesadilla making? Email chain management? Flex those muscles, playa.
7. What was the worst purchase you’ve ever made?
Buyer’s remorse is real. What does he regret?
8. What did you think was silly until you tried it?
Is he the type of guy who is willing to leave his comfort zone?
9. What is the most irritating food?
Sometimes the taste is worth the work.
10. What’s the best prank you can play on someone?
This question will tell you a lot about his sense of humor.
11. If you wanted to give a tourist the local flavor of where you live, what would you have them do?
Give him a chance to brag about his hometown and find out his interests.
12. If you could make everyone in the world believe one thing (regardless of whether it’s true or not), what thing would you choose?
Belief is a powerful thing.
13. What was your biggest experience of “culture shock” in another country?
This question can lead to a great conversation about travel and culture.
14. If you could add 4 hours to your day, what would you spend that 4 hours doing?
Most of us wish we had more time. How would he put that time to use?
15. Who would be the worst celebrity to have dinner with?
Pop culture is full of people with questionable table manners.
16. What really annoys you when other people do it, but you occasionally do it as well?
Our pet peeves tend to be things we don’t like about ourselves.
17. If you were given the ability to make one new trend and it be instantly popular, what trend would you create?
Modern society has seen its share of odd fads. What trend would he set?
18. What’s the best $5 you’ve ever spent?
Sometimes value has nothing to do with a price tag.
7 Best Interesting Questions To Ask A Guy
We all want to come across as interesting, and the easiest way to pull it off is with interesting questions. When you want to impress a guy, it follows then, all you need are interesting questions to ask a guy.
Use a few of these questions to get beyond the basics and talk about something a little more...interesting.
Here are 7 best interesting questions to ask him:
19. What was the funniest way that you have been injured?
Guys like to talk about their scars. Here's a chance for a good story.
20. Which movie do they need to a sequel to?
Every guy has a movie instantly in mind.
21. What simple change could you make in your life that would have the biggest positive impact?
You'll be surprised at the honest answers to this one.
22. When have you been with a person and thought you were equals, but then discovered they were on a whole different level?
A bit philosophical, but the answers can be truly interesting.
23. What is your dream job and what makes it so amazing?
Find out just what they really wish they could be.
24. What is something most people do easily but you find very difficult?
Let them show a little honesty and humility.
25. What was your best drop the mic moment?
Watch how eager he is to tell you this one.
21 Best Funny Questions to Ask a Guy
Everyone loves being around people who can make them laugh. It’s a universal truth.
Even more than that, people love a chance to make others laugh.
This list of funny questions to ask a guy will allow you to show your sense of humor while giving the guy you’re talking to a chance to do the same. It’s a win win! Drop a few of these funny questions in one on one situations or in a group of guys and you’ll leave everyone feeling more positive and confident.
Here are 21 best funny questions to ask a guy:
26. What is society doing now that in 20 years will be laughed at and ridiculed?
What will 2017’s version of the mullet be?
27. What were you really into when you were younger but now think is silly?
What makes him cringe when he looks at old photos?
28. What was the weirdest habit you had as a child?
Kids are weird. Laugh at the strangeness of youth together.
29. What are you so incredibly terrible at, that you’ve given up ever doing it again?
There’s bound to be a good story behind this one.
30. What would be the worst store to have a $1,000 gift card for?
Most guys could spend a grand pretty easily, but some stores make it a challenge.
31. If there were an Olympics for average people, what would some of the events be?
Competitive itch scratching? Underwater nail trimming?
32. What’s the biggest “scene” you’ve seen someone make in public?
Witnessing a public meltdown can be fun… unless you’re involved.
33. What have you done wrong for most of your life and only recently found out the right way to do it?
Give him the chance to share his life hacks.
34. What one toy do you wish never existed?
Toys are supposed to be fun!
35. If you instantly turned into a woman for a day, how would you spend that day?
Every guy has imagined it. Plan your dream ladies day together.
36. You can only eat one thing for the rest of your time on earth. What do you eat and why?
Finally. All you can eat nachos.
37. Have you ever watched really terrible children’s television just because you were bored?
After the 3rd episode the characters really draw you in.
38. What’s the worst movie you’ve ever paid to see?
Follow up with: who approved that movie in the first place?
39. What's the grossest thing you've ever eaten?
Can he top worms, every kid’s secret snack?
40. What’s the most cringeworthy thing you’ve ever said to someone you were attracted to?
There’s a certain joy in comparing flirting fails.
41. What is the funniest dream that you had that you can recall?
The impossibility of dreams can lead to comedic gold.
42. What is the cheesiest pickup line you’ve ever tried to use on a girl?
And more importantly… did it work? Here are some cheesy pick up line options.
43. How long do you think you’d survive a zombie apocalypse?
Gauge the man’s survival skills. You just might have to team up.
44. What’s something that always makes you laugh?
It’s good to know where to turn when you need a pick-me-up.
45. What’s a song that no one knows you like?
Guilty pleasure songs are the best songs.
15 Best Questions to Ask a Guy to Get to Know Him
At some point you’re going to want to move beyond the small talk.
Small talk has its place, but for more lasting relationships you’re going to need some getting to know you questions to take your budding friendship to the next level. You know you’re ready to bypass the trivia and ask questions to get to know a guy when you can tell that the two of you have common interests or personalities.
As some of these questions dip into personal matters, you’re going to want to wait until you’ve established a rapport before you ask a guy these questions.
Here are the 15 best questions to get to know a guy:
46. Who or what do you always have time for?
How a man prioritizes his life will tell you volumes.
47. If time wasn’t an issue and you had forever to master a skill, what skill would you master?
Eliminate busyness and what would he accomplish?
48. What’s something everyone should experience at least once in their life?
Allow him to share the experiences that have impacted his life.
49. If someone wrote a biography about you, what do you think the title should be?
This question asks him to describe himself in just a few words.
50. What bad habit do you have that you know you need to break, but don’t really want to?
Our indulgences make us human, but so does the struggle to improve.
51. If money were no object, where in the world would you choose to live?
A place from his past, or the place of his dreams?
52. What small thing makes you angrier than it should?
This will be good to know as you develop a bond.
53. What would you include in a time capsule?
What object does he see as representative of this period?
54. What one thing would you most want to save if your house caught fire?
Is his most valuable possession sentimental or monetary?
55. What two things are you most passionate about?
Our passions guide us through life. Where is he being led?
56. What are you too old for but still enjoy?
Can you ever outgrow childhood pleasures?
57. When was the last time a stranger made your day?
Acknowledging the kindness of others is a great trait.
58. What have you really wanted to do for a long time but haven’t done yet?
Take the opportunity to encourage him to take the next step.
59. What’s your definition of a good human being?
What are the qualities mankind should strive for?
60. What quote has always stuck with you?
Does he have words of wisdom that he lives by?
15 Best Random Questions to Ask a Guy
Random questions are a great way to shake up a conversation.
Like hitting shuffle on your favorite playlist, you never know what direction things will go, but you can bet it will be fun. Some of these random questions to ask a guy are funny, some are weird, but all are sure to lead to fun chats.
Here are the 15 best random questions to ask a guy:
61. What would be the absolute best pet to have?
Imagine dogs and cats aren’t options. I hear tigers are nice.
62. Which fictional villain is your favorite?
Sometimes there’s something appealing about the antagonist.
63. Who are you most like, Michael Scott, Dwight Schrute, Andy Dwyer, or Ron Swanson?
Sure, you can mix and match.
64. If you made up an ice cream flavor, what would be in it?
Bacon maple already exists, so the bar has been set.
65. If you were a biker, what would your biker nickname be?
Every man needs a macho alter ego.
66. Faced with starvation, what would you still never eat?
Even when faced with certain death, man will remain stubborn.
67. You're a criminal mastermind — what do you leave at the scene of the crime as your calling card?
Sometimes infamy sounds as good as fame.
68. If you could create an app that could do anything, what would it be?
There’s an app for almost everything. How else would he make life more convenient?
69. If you had to eliminate one day of the week, which one would you eliminate and why?
A case can be made for most days. But leave Saturday out of this.
70. What’s the funniest lyric you’ve ever misheard?
I’ve been wondering where Jason Waterfalls went for years.
71. What is the most hideous fashion fad that you’ve ever seen?
Pick a decade and something horrible was worn. Which takes the cake?
72. What is one superpower you would hate having?
Some attributes only get worse when enhanced. Super smell? No thank you.
73. Out of all Solar System planets, which one would you like to visit most?
We’ve never landed a man on another planet. If he got the call, where would he go?
74. If you could take one book to a desert island, which book would that be?
A person’s favorite book says a lot about them.
75. What is the first thing you'd do if you heard about the outbreak of zombie apocalypse?
Most guys day dream about this. He’ll likely have an answer right off the bat.
5 Best Personal Questions To Ask A Guy
Sometimes you meet a guy you really get along with and you can see the two of you becoming friends.
To do that, you'll have to ask him personal questions. And it's not as hard as it sounds!
For tips, check out our list of personal questions to ask a guy and be sure to scroll down to see the best of them.
Here are the 5 best personal questions to ask a guy:
76. Do you like to take suggestions from others before you take any decision?
Depending on the decision, it's usually a good idea to get a second opinion.
77. How do you spend your free time?
A classic get to know you question.
78. What kinds of clothes do you prefer and why?
This one is especially good to ask a guy who knows how to dress well.
79. What are your favorite hobbies?
If he has the same hobbies as you, the two of you can team up on it!
80. If you had a chance to visit one place in the world which place would you pick?
Everyone has a dream destination.
15 Best Personal, Deep Questions to Ask a Guy
Even people who’ve known each other for a long time can somehow avoid personal topics.
There’s nothing necessarily wrong with that, but as guys we crave a strong bond with other men. If you want to get to know the guys around you on a deeper, more personal level, you need the best deep questions to ask. These questions can be the beginning of a transition from acquaintance to friendship or a way to reconnect with with an old friend you’ve grown apart from.
Here are the 15 best deep, personal questions to ask a guy:
81. If you could run away from it all and start fresh somewhere new, would you?
This question will let you know if he’s content in life or living with questions
82. What are your life and career goals in 5, 10 and 15 years?
A man's goals determine the direction of his life. Where is his life headed?
83. Which do you follow—your heart or your head?
Men like to think they are logical creatures, but some men are ruled by passion.
84. How does your definition of a “real man” differ from the mainstream stereotype of a “real man”?
Are muscles and money all it takes to be a man, or is there something else?
85. What was a random compliment that someone gave you that really stuck in your memory?
Unexpected compliments can be the most meaningful. What trait of his was randomly appreciated?
86. What do you judge people for that you probably shouldn’t?
Everyone struggles with prejudice. How we deal with it is what matters.
87. What was the last major goal you accomplished?
He will love having the opportunity to share his most recent victory.
88. What’s one thing you learned this week?
You want to surround yourself with people who are learning and growing. Find out if this guy is.
89. Do you think your childhood was better or worse than other people growing up in a similar place and time?
Childhood, whether good or bad, shapes the rest of our lives.
90. What rules do you make for yourself?
All men should have a code. What code has he set for himself?
91. What are your three weaknesses/strengths?
There’s a reason this is a common interview question. What a person considers to be their own strengths or weaknesses is very telling.
92. What’s the single most important thing you have done in your life?
This question goes back to values. Does he tie importance to work? Family? Community?
93. Would you rather correct a mistake from the past, or receive an answer from the future?
Would he take the chance to right a wrong or prevent future harm?
94. What has had the biggest impact on your political beliefs?
There are few things more personal than politics.
95. What are you most grateful for in your life?
Give him a chance to acknowledge the things in his life that he’s thankful for.
15 Best Would You Rather Questions for Guys
Would you rather questions are a time tested method of starting conversations.
Whether you’re want to make the fellas laugh or make them think, there’s a question on this list that will fit the bill.
Here are the 15 best would you rather questions for guys:
96. Would you rather go a week without bathing, but be able to change your clothes, or a week without a change of clothes, but be able to bathe?
Either way he won’t be making many friends in the elevator.
97. Would you rather climb harsh mountain cliffs or hike through rough deserts?
Both are challenging, but would offer great satisfaction on the other side.
98. Would you rather have money but no control or control but no money?
The two go hand in hand, but if he had to have one without the other which would it be?
99. Would you rather earn more money doing the wrong thing or less money doing the right thing?
Which is a bigger motivator: ethics or profits?
100. Would you rather be the strongest on earth or the smartest on earth?
The age old question: brains or brawn?
101. Would you rather be clever and alone or dumb and surrounded by people?
Is intelligence worthwhile with no one to share it with?
102. Would you rather earn less by the job you love or earn more by the job you hate?
At a certain point, one must choose between money and contentment.
103. Would you rather be a boss with the worst employees or an employee with the best boss?
Having a vision with no one to carry it out, or carrying out someone else’s vision?
104. Would you rather save your friend who is the culprit or the random person who is totally innocent?
Is the bond of friendship stronger than the call of justice?
105. Would you rather live with only gadgets forever or with only humans forever?
Some men are more technologically inclined, while others are more social.
106. Would you rather live in a room for a year or live in a jail for 6 months?
House arrest or hard time? Hopefully you’re never faced with this decision.
107. Would you rather live a long life with no money or short life with lots of money?
It’s funny how “you only live once” can lead people in such polar opposite directions.
108. Would you rather be lost in the mountains or stuck in the office forever?
Would he choose freedom in harsh conditions or confinement in comfort?
109. Would you rather have great sense of humor with below average looks or great looks but no sense of humor?
Not everyone can be Ryan Reynolds. If he had to pick one trait, which would it be?
110. Would you rather win the newest iPhone or win a dream vacation?
The temporary bliss of a vacation or the more permanent use of the newest tech?
How to Ask a Guy Questions
Making friends is natural when you’re young, but it takes work when we reach adulthood. Before you dive into these questions, let me give you some tips on how best to use them.
1. Get Your Mind Right
Remind yourself why you’re looking for questions to ask guys.
If you’re looking to make meaningful connections with new people, start with the conversation starters and progress towards the deep, personal questions.
If you’re looking to fill the silence with a guy you see regularly but don’t anticipate a close friendship, lean into the random questions and would you rather questions. But be warned: you might end up with a new friend anyways.
2. Consider the Context
Don’t ask your coworker a deep question in the middle of a department meeting. And maybe don’t ask a funny question to the guy currently trying to get a new max on his bench.
A poorly timed question is worse than an unasked question. Wait for a moment when conversation seems natural, and if that moment doesn’t come create it!
3. Be Brave
If you’ve been reading up on ways to strike up conversations with other men, you can bet you’re not the only one. Mankind craves communities.
Remember that the chances are good that the guys around you are open to conversations and new friends.
Don’t be nervous. He’s just another guy. Strike up a conversation.
Downloadable and Printable List of Questions to Ask a Guy
Here is a downloadable and printable list of questions to ask a guy (right click the image and select Save Image As...):
Looking for More Questions to Ask a Guy?
By now you have dozens of great questions to ask the fellas in any situation. Ranging from conversation starters to deep questions, with some funny and random questions thrown in along the way.
If you’re still looking for more questions to ask a guy, I’ve got some resources that you’re sure to find interesting and helpful.
- If you enjoyed the would you rather questions, check out our list of this or that questions. They’re great for starting conversations and gauging a guy’s interests.
- Keep things light and interesting with some fun get to know you questions. Whether you’re buying rounds at your favorite watering hole or getting to know the fellas at work, fun questions are always welcome.
- Believe it or not, many items from our list of questions to ask a girl work really well with guys too. After all, the purpose is the same - you want to find if you have a connection with another person.
You now have the ultimate resource for getting to know other guys.
These questions to ask a guy are designed to help you turn strangers into friends and make it easy for you to get to know the guys around you. Keep in mind that the purpose of these questions is to help you connect with other guys, so listening to answers is just as vital as asking questions. Don’t interview the man, get to know him!
Start using these questions to ask today, and watch as you become more comfortable at work, at the gym, or out on the town.