Knowing a handful of good questions to ask a guy to get to know him is essential.
…Because like a lot of guys have found:
Whether you’re expanding your circle of friends, meeting a new co-worker, or just hanging with an unfamiliar crew, knowing the right questions to ask can keep the conversation flowing and minimize uncomfortable silences. These questions are fun and casual, but they can lead to interesting, in-depth discussions.
These are the perfect questions to ask a guy if you’re starting from a blank slate. If you already have a rapport with someone, you may want to focus on more specific topics, and then use these get to know you questions to spice things up every so often.
Even the boldest and wittiest among us have trouble thinking of something to say at times. That’s normal. Keep these handy questions to ask a guy to get to know him on deck, and bust them out when you’re drawing a blank.
Start simple. These conversation starters are perfect for when you just met someone. Even if you don’t know a single thing about the other person, these easygoing questions to ask to get to know a guy can spark a more in-depth discussion.
Here are 20 conversation starters to get to know a guy:
1. Do you think that fish ever get thirsty?
Fun and deceptively simple, this question forces you to imagine what it’s like being an entirely different species. It also makes you think about how we perceive water, thirst, and the world around us.
2. What’s your all-time favorite movie?
A classic conversation starter that can lead to hours of debate. Sell him on your favorite film, but keep an open mind when he explains the reasons behind his.
3. If you could know more about any one thing, what would it be?
This question is a window into his deepest interests. It gives the guy the chance to talk about his favorite topic, and you might even learn a thing or two.
4. What do you think the absolute coolest hobby out there is?
This is another question that helps you understand what he’s all about. Whether he’s into woodworking or competitive dog grooming, you’ll have plenty to discuss. Here’s a list of our favorite hobbies for men.
5. What is something you’d like to make with your own hands?
It’s no secret that guys enjoy projects. If the tools and materials were ready to go, what would he love to create?
6. Past or present, who’s your favorite athlete?
Even if he isn’t a sports fan, most people have at least one athlete they look up to.
7. If you could permanently change one movie ending, what would it be?
We’d all like to put our own twist on a movie. Give him the chance to play M. Night Shyamalan for a few minutes.
8. Where’d you grow up?
It’s a simple conversation starter, but it opens up a world of discussion.
9. What’s your favorite place that you’ve ever traveled to?
Besides opening plenty of topics to discuss, a person’s favorite vacation spot says a lot about their interests and world view.
10. What’s your sport?
Whether he’s an athlete or a fan, guys tend to have no problem bonding over sports. If nothing else, you can argue why yours is better.
11. If you could be personally trained by any athlete, who would it be?
This question is kind of like asking about his favorite athlete, but it opens up the discussion into why the chosen athlete would be the best choice as a personal trainer.
12. Who do you think is the most interesting person currently alive?
There are plenty of characters out there. Which one does he find most fascinating, and why?
13. If you could only keep one non-sentimental possession, what would it be?
This question helps you understand what kind of activities or possessions are most important to him in his life.
14. If the world froze for an afternoon and only you could move and no one could see you or remember what you did, what would you do?
This question definitely opens up plenty of room for imagination.
15. If you could permanently remove one product from existence, what would it be?
We’ve all asked ourselves why and how certain products exist. What are the worst of the worst?
16. If you went into a coma and woke up in the year 2120, what would be the first thing you would want to know?
This conversation is fun to think about, but it also makes you consider what’s really important to you right now.
17. What’s something that’s fine in small numbers, but terrifying in large numbers?
What makes your skin crawl as the numbers grow? Don’t be afraid to get weird with this one.
18. If you could travel back in time, capture one person, and bring them to present day, who would it be and why?
A question with no right or wrong answer, this conversation starter can lead to a long discussion about history, morality, and the implications and paradoxes that come along with changing the past.
19. What is the best/worst food you’ve ever tried?
Everyone eats. Light and easy, this question is perfect with complete strangers and new friends alike.
20. If you could shrink or grow any animal to the size of a horse, what would be your ride of choice?
Whether he wants to pilot a bee or go duckback riding, this conversation starter is great for laughs.
After you’ve kicked things off with conversation starters, you should be feeling more comfortable. Keep the conversation moving with these questions.
Here are 15 of the best questions to get to know a guy:
21. If you could be an Olympic athlete, what sport would you compete?
Most guys have envisioned themselves competing in the Olympics at some point.
22. What do you think is the greatest invention of all time?
And why? This question really opens up the possibility for silly or intelligent discussion.
23. If you had to give up alcohol or coffee, which would you choose?
What’s your vice? And, no, water isn’t an option.
24. What can you do today that you couldn’t do a year ago?
This question may require some thought and self-reflection. It also helps both of you to relate over changes in the world.
25. If you were put into solitary confinement for six months, what would you do to stay sane?
What’s your happy place? This question helps you learn what makes him tick.
26. If you were the only human left on Earth, what would you do first?
After the existential crisis wears off, of course. How do you spend your time? Where do you go, and what do you do there?
27. Okay, then what would you do?
Let’s say a week has passed. Then a month. A year? How do you fill the days as the last remaining legend?
28. What’s the thing highest up on your bucket list?
Most guys have some lofty goals they’d like to accomplish before croaking.
29. If you had to give a TED talk tomorrow, what would it be about?
This question can reveal passions, knowledge, and expertise that you may not have known about. If you had to give a 20-minute lecture with minimal preparation time, what topic would you choose?
30. If you could steal the talent or intelligence from any one person, whose would you steal?
The people you look up to say a lot about you.
31. If you could teleport anywhere in the world right now, where would you go?
This simple question literally opens up a world of conversation possibilities.
32. What’s the most boring superhero you can come up with?
The drabber the better. Bonus points if you can think of an equally lame villain.
33. Would you become a professional bank robber if you knew you would never get caught?
This question is generally lighthearted, but it can shed some light on his morals.
34. Would you rather have the super power of strength or invisibility?
Would you rather sneak or clobber? It’s a fun question that helps you learn what kind of person he is.
35. What’s the best $20 you’ve ever spent?
Whether you’re getting a shopping tip or hearing a story, it’s a win-win.
Guys aren’t always the easiest to get to know, but if you ask the right interesting questions, they’ll open right up.
The key to curating your personal list of interesting questions to ask a guy is to choose questions that fit the guy in front of you, not just a generic guy.
Take a handful of the questions below so you’ve always got a good one available.
Here are 8 best interesting questions to ask a guy to get to know him:
36. Who or what is your nemesis?
It’s silly and yet broad enough every guy has an interesting answer.
37. What long shot have you taken that really paid off?
Give the guy a chance to talk about when he was lucky and brave. He’ll have a great story behind it.
38. What were you really into when you were younger but now think is silly?
A great way to talk about personal growth.
39. What is the highest pressure situation you have experienced and how did you handle it?
Expect some surprising answers here.
40. Who has completely lost your respect?
An opener to a potentially controversial, and very interesting, conversation.
41. What one question can you ask someone to find out the most about them?
Find out, then ask the guy.
42. What was the weirdest habit you had as a child?
We were all weird as children. Get him to relive his weirdest moments.
43. What’s the best bad decision you’ve made?
You may learn about the bad decisions you should take next time.
Guys like to make each other laugh. It’s probably hard-coded in our DNA. Crackin’ wise with the boys is a timeless pastime in and of itself, so don’t overlook these funny get to know you questions.
Never underestimate the power of humor when it comes to connecting with people. These getting to know you questions may be lighthearted, but they’re extremely effective.
Here are 20 of the best funny get to know you questions:
44. Alright, let’s get real, what’s your favorite Disney Channel original movie?
This one is probably going to come out of left field, and that’s what makes it hilarious. Bonus points if you can discuss characters, plots, and symbolism.
45. Would you rather never use the internet again or never watch TV again?
This question is a tech-junkie’s worst nightmare. Do you give up memes or programs?
46. What’s the most ridiculous fact you know?
“Ridiculous” can mean a lot of things. Mind-blowing, hilarious, and flat-out bizarre facts are all acceptable.
47. What’s the worst movie you’ve ever seen?
That movie that made you want to write an angry letter to the director. Let’s hear about it.
48. If you had your own flag, what would be on it?
You’re finally buying that private island you’ve been talking about. What’s your country’s insignia?
49. Why does a round pizza come in a square box?
These are the questions that keep today’s greatest minds up at night. What do the corners accomplish?
50. Would you rather be turned into a hologram or into 2-dimensions?
Three-dimensional living is no longer an option. What’s your plan?
51. Would you rather not shower for a week or not brush your teeth for a week?
Either way, do the rest of us a favor and don’t leave the house.
52. If Batman and Superman fought, who would win?
An enduring question that has plagued guys of all ages for decades.
53. What’s the manliest thing you’ve ever done?
What was your peak male experience? Whether he rescued kittens from a burning building or built a sword with his bare hands, this question gives him the chance to brag a bit.
54. Would you rather speak all languages or be able to speak to all animals?
Would you rather communicate with your fellow human, or the creatures of the Earth?
55. If you could live only one day, over and over again, what would you choose to do?
The classic Groundhog Day scenario. Where would you want to be, and what would your day look like?
56. What do you do to make the world a better place?
Slightly accusatory in a tongue-and-cheek way, this question forces him to defend his worth.
57. If you had to start a collection of one kind of items, what would it be?
There are so many possibilities. This question can really get you thinking about weird collections. Lawn flamingos? Troll dolls? What would you fill your home with?
58. If you had to spend the rest of your life in a tree, what kind of tree would it be?
No, a tree house does not count.
59. Would you rather be a hobbit or an elf for the rest of your life?
Would you prefer a life of leisure, or the responsibility of immortality?
60. What would be the worst food to be liquefied and drunk through a straw?
Create the milkshake of your nightmares.
61. What is/was the worst trend of all time?
That fad that still makes you cringe to this day. Out with it.
62. What’s your favorite joke?
Straight to the point. Everyone loves a good joke.
63. Which fictional character (movie, video game, cartoon, book, etc.) would have the hardest time assimilating into society?
This question is great because it lets you both discuss your favorite characters while also discussing their place in the real world. Learn about the guy’s tastes while sharing a laugh at the same time.
When you want to get to know a guy on a personal level, your best bet is with personal questions.
We’ve compiled a fantastic list of personal questions to ask a guy and bring you the best of them below.
Here are 5 best personal questions to ask a guy to get to know him:
64. What’s the most ridiculous thing you’ve seen online recently?
There’s never a shortage of nonsense on the internet.
65. Where’s your favorite place to get take away or delivery from?
Everybody has a favorite restaurant! You might find your newest food obsession!
66. What app on your phone do you think I should get?
Any guy who doesn’t answer, “The Mantelligence App” doesn’t know what he’s talking about.
67. Do you have any special memories of your first love?
Open the flood gates. Those memories are rushing back.
68. What was the worst year of your life?
Tough times only make us stronger and more prepared to tackle the next ones.
The previous questions have been pretty surface-level. While some of them may inadvertently help the guy you’re with to open up, they’re not designed specifically with that goal in mind.
These deep questions to ask guys can get introspective, heartfelt, and even emotional, and there’s nothing wrong with that.
Save these questions for when you’re feeling comfortable talking about personal topics. They may not be right for business relationships, but they can help to solidify a budding friendship.
Here are 17 of the best questions to ask a guy to get to know him deeper:
69. What is the last thing that you’ve done that’s really worth remembering?
This question shows that you’re genuinely interested in his goals and accomplishments.
70. What is the best piece of advice you’ve received?
In addition to giving you a new wisdom gem to internalize, this question can help you see the world through his eyes. Be sure to also ask about the person who gave the advice, as well as the context involved.
71. What was the last experience that made you a stronger person?
Everyone goes through trials and tribulations that help to make us more powerful and resilient. Don’t pry if he doesn’t want to talk about an event that’s still raw.
72. What’s something horrible that you think everyone should do/try at least once?
Terrible experiences can build character. Ask him about his negative moments that turned out positive in the long run.
73. Who is someone in your life that you want to be like when you are older?
Knowing a person’s role models can help you to understand their actions.
74. What law would you change?
This question can lead to a million and one other conversations. It really sets you both up to discuss morality, current events, and how you view the world and society in general.
75. What makes someone a hero?
Not all heroes wear capes. In fact, very few do. What are the actions and characteristics that make someone truly admirable?
76. How much do you know about the world outside your country?
Whether he’s a world traveler or someone who prefers the comforts of home, asking about his global perspective is a simple recipe for good conversation.
77. How would you explain your basic life philosophy?
Take this question a step further by asking him to boil that philosophy into one key phrase.
78. What was the most rewarding thing you’ve ever done?
Those moments that stick with us for a lifetime. Talk about them.
79. How would you define “freedom”?
It’s a word that means something different to many people. This question opens up plenty of possibility for a healthy debate on a number of issues, philosophies, and viewpoints.
80. If you could eliminate one weakness or limitation in your life, what would it be?
Nobody is invincible. Discussing your shortcomings and meeting them head-on is empowering. If you know each other’s weaknesses, you can help each other in times of need.
81. When did you realize you’re not a kid anymore?
Some people have that ‘a-ha’ moment when they realize they’ve hit adulthood. For others, it’s a slow build.
82. How do you define “honesty”?
Is it telling the truth, no matter what? Or is there such a thing as a white lie?
83. What is one quality you admire most in others?
This question helps you to understand the inner-workings of the guy you’re talking to.
84. What is the most important thing you learned from your parents?
A person’s family is a huge part of who they are. Understanding where he comes from is critical to getting to know him deeper.
85. What is the number one change you need to make in your life this year?
Life is a journey, and the path requires ongoing adjustments. Learn about the changes he needs to make, and help him along the way.
We all know how tough it can be…
Here are 6 powerful tips to help you get to know a guy:
Tip #1: Choose your questions wisely
The questions you ask at a bar with your bros are probably going to be different than the questions you ask a potential business partner at lunch. Don’t choose these questions to ask to get to know a guy at random. Think about where you are and who you’re with.
Tip #2: Go with the flow
Try to size up the guy’s interests and personality, but don’t always assume you’re right.
Once the conversation starts flowing, you’ll be able to determine which questions are going to work, and which might not land. In the meantime, start simple.
Tip #3: Don’t be pushy
There’s nothing wrong with the occasional comfortable silence. Keep things light. Don’t grill the other person. Subtlety is far too often lost when it comes to the art of learning how to get to know someone.
If you’re asking one rapid fire question after another, you’re going to end up overwhelming your company. Conversation, not interrogation.
Tip #4: Be a part of the discussion
These questions to ask a guy to get to know him aren’t free passes to avoid contributing to the conversation. The only way to get to know someone is to open up.
After you ask a question and receive an answer, give your take. Learning about the other guy is half the battle. You want him to also get to know you. That’s how bonds are formed.
Tip #5: Change the mood
Tip #6: Listen
You’ll get your chance to speak. You’re asking questions, so listen to the answers. People can tell when you’re asking questions just for the sake of keeping awkward silences at bay.
Meeting new people is fun and interesting, so don’t tune them out. Be genuine.
Downloadable List of Questions to Ask a Guy to Get to Know Him
More Great Questions to Ask a Guy to Get to Know Him
With these questions to ask a guy to get to know him under your belt, you should be able to handle virtually any social interaction with an unfamiliar guy. Of course, it never hurts to add a few more to your arsenal, so here are some more awesome questions to ask:
- If you’re looking for some more conversation fuel, these 20 Questions to Ask a Guy should fit the bill nicely. Memorize them or load them up in your phone for easy reference.
- If you’re pursuing someone on a romantic level, you need to use the right questions. After all, guys and girls tend to be wired differently. These Questions to Ask to Get to Know a Girl should help you to be your charming self so you can really connect with her on your next date.
- Asking direct questions is a great way to get to know someone quickly and easily. That said, it also helps to have a variety of Conversation Topics ready to go. Keep these topics in the back of your mind so you can keep the conversation going naturally between questions.
Authenticity goes a long way. These get to know you questions make excellent starting points, but don’t forget to add your own personal touch. Get inspired by these questions to get to know a guy, and use them to ignite conversations about all sorts of other topics.
Remember: each and every person is unique. Enjoy the excitement of connecting with someone new. Having a wide range of questions to ask will help, but it’s up to you to use your winning personality to form meaningful relationships.
Try not to overthink it, and above all else, have fun!