360 Questions to Ask Guy | ConversationStarter.com

Starting a conversation with a guy can be exciting, but it’s not always easy to know what to ask to keep things flowing naturally. Whether you’re getting to know a crush, a friend, or even a coworker, having the right questions up your sleeve can make all the difference. The key is to ask things that spark genuine interest and lead to deeper, more meaningful interactions—without feeling forced or awkward.

These questions to ask a guy are designed to cover a wide range of topics, from light and funny to thoughtful and personal. Whether you want to discover his interests, uncover hidden dreams, or simply share a laugh, these conversation starters are sure to help. They’re perfect for breaking the ice, strengthening connections, and even unlocking parts of his personality that you may not have seen before.

Good questions to ask a guy

If you could make one belief instantly universal across the world, what would it be?
What common advice or motivational quote do you think is overrated or doesn’t really make sense?
If you were given the chance to colonize a new planet but could never return to Earth, would you do it?
If you were a ghost, what kind of haunting tricks would you play?
What’s one simple daily habit that could drastically improve someone’s life?
What’s a common practice in your culture that would sound strange or ridiculous if explained to an outsider?
If life worked like a video game, where would you invest your next skill upgrade?
What’s something you’ve been doing wrong your whole life but only recently learned the correct way?
What’s an experience you think everyone should have at least once in their life?
If you were an actor, what types of roles would you be perfect for?
What’s a social media post that left a lasting impression on you?
What’s your all-time favorite board or card game? Which one do you never want to play again?
What would you suggest to someone who has a full day off but no idea how to spend it?
What’s something society does now that will be laughed at in 20 years?
If you could show the world one image for 10 seconds, what picture would you choose and why?
If you could be frozen at one age for the rest of your life, what age would you choose?
You wake up in the dead of night—what sound would terrify you the most?
Who has lost your respect completely, and why?
You have $1 billion to make insects a popular food—how would you do it?
What’s something you believe, even though you know it’s probably wrong?
What’s something you were really worried about that turned out to be no big deal?
Who is your all-time favorite author, and why?
If you could instantly become a virtuoso at any instrument, which one would you pick?
What’s your top podcast recommendation for someone looking for something new?
What small, seemingly insignificant thing instantly gets under your skin?
If you had to devote your life to one cause, what would it be?
What quote has stayed with you and impacted the way you live or think?
What are your go-to movies across different genres?
What’s the biggest uncertainty that keeps you up at night?
If life could mirror any movie, which one would you choose?
Who is famous for their “talent” but really doesn’t deserve the hype?
If your house caught fire and all living beings were safe, what item would you save first?
When was the last time life threw you a curveball that felt a little too real?
What’s the most confusing English idiom or phrase for non-native speakers?
What’s one powerful question you could ask to learn the most about someone?
What’s the last major goal you worked hard for and accomplished?
Who is your favorite fictional villain, and what makes them stand out to you?
What animal would you least want to be eaten by, and why?
How do you picture the day-to-day lives of super-wealthy people?
What high-level job could you bluff your way into without getting caught?
What’s a random compliment you received that you still think about?
What’s something you absolutely wouldn’t do, even for 5 million dollars?
If you had four extra hours in your day, how would you spend them?
What’s the most stressful moment you’ve had, and how did you get through it?
When was the last time you felt completely out of the loop or disconnected from everyone around you?
What random fact or piece of trivia have you memorized that will probably never be useful?
If you could cast one spell to do a boring, everyday task, what would it be for?
What’s the most ridiculous or unnecessary rule you’ve ever had to follow?
Who’s someone you met only once but left a lasting impact on you?
What’s the most significant or historic moment you’ve ever witnessed or participated in firsthand?
What unique qualities or talents set you apart from others?
What’s a traditionally feminine activity or hobby that you really enjoy?
What’s something you thought was ridiculous until you gave it a try?
What’s a common misconception that most people believe but you know is wrong?
What’s your best one-liner or joke that never fails to get a laugh?
If you could create a trend and make it go viral, what trend would you introduce to the world?
What’s the worst slip of the tongue you’ve heard about or experienced firsthand?
What’s a strange habit you had as a kid that you still remember?
What’s a long shot you took that surprisingly worked out perfectly?
What’s the most pointless skill you’ve mastered?
What image or design do you have as your phone or computer wallpaper, and why?
What’s the best and worst thing about being a guy?
What’s a childhood habit or activity you still enjoy as an adult?
How would you define a genuinely good person?
If you could go back in time and introduce a modern invention to an earlier civilization, which invention would you choose, and when would you introduce it?
If today was your last day, what would you consider your biggest achievement?
If the world united under one global government, what city would you choose as its capital, and what would its anthem and flag look like?
If you had the chance to leave everything behind and start over somewhere new, would you take it?
Is there a product or company you quietly boycott without making it public?
What would your complete opposite be like if they existed?
What are two things you would never, under any circumstances, spend your money on?
If you could create one universal rule for internet users, what would it be?
What’s the closest you’ve come to disaster without it happening?
What’s something you think you’re an expert in, but probably aren’t?
What’s the earliest memory you can recall from your childhood?
What do you consider to be a masterpiece created in the modern era?
What’s the most absurd thing you’ve seen become a reality in recent years?
On a scale from “existential crisis” to “living the dream,” where would you rate your life right now?
What’s an obscure website or online resource you absolutely love?
What’s something you were obsessed with as a kid but now find silly?
What’s the worst purchase you’ve ever regretted making?
What’s a topic you could confidently give a 30-minute presentation on right now?
What minor “first world problems” irritate you even though you know they shouldn’t?
When was the last time a random act of kindness from a stranger made your day?
Who or what is your ultimate rival or nemesis in life?
What’s the best thing you’ve ever bought for $5 or less?
What’s something that happens to you more often than you’d like?
What’s the weirdest or most ridiculous tattoo you’ve ever seen?
If you could watch only one last movie before you die, what would it be?
What store would be the most disappointing to receive a $1,000 gift card for?
If you could turn life into any video game, which one would you choose and why?
What’s something you’ve done to make the world a little better?
Who would you cast to play you in the movie version of your life story?
Do you collect anything, and if so, what is it?
What food do you find the most annoying or frustrating to eat?
What’s a movie you could watch on repeat without ever getting bored?
What’s the highlight of your day that you always look forward to?
If the U.S. states had personalities and could date each other, which states would be the best match and why?
What non-political, non-religious topic always sparks heated debates among your friends or family?
Which historical figure is way more overrated than people realize?
Have you ever witnessed someone play the “Do you know who I am?!” card, and what happened?
If you could see any headline in tomorrow’s news, what would it say?
What’s the one game you always seem to lose no matter how hard you try?
What’s the most bizarre but fun experience you’ve had?
What’s a goal or dream you’ve been wanting to pursue but haven’t started yet?
What’s your favorite creative outlet or hobby?
What’s the most effective way for a government to control its citizens?
What’s the ultimate prank you’ve either pulled off or would love to try?
What would the ultimate $20,000 party or event look like if you were in charge of planning it?
What’s a strange flavor combination that you can’t get enough of?
Which celebrities do you think are most likely to be rude in real life?
What’s something you own that always catches people’s attention or sparks comments?
How would life change if scientists discovered a way for humans to live for 500 years?
What’s one piece of advice you think the world would be better off following?
What’s your wildest or most frustrating customer service experience?
What’s something so obvious you can’t believe you didn’t notice until someone pointed it out?
What’s the weirdest or most unusual thing you ate as a kid?
What’s something you’ve tried and failed at so many times that you’ve given up on it completely?
Which fictional character did (or do) you secretly have a crush on?
What’s something you’ve done countless times but still haven’t mastered?
What’s something you believe can only be fully appreciated when experienced in person?
What’s an extreme act of kindness you’ve witnessed or heard of that left you in awe?
How does your idea of a “real man” differ from the stereotypical or traditional image?
What’s your ultimate mic drop moment that you’ll never forget?
What small, simple pleasures bring you an unexpected amount of joy?
You’re given $300,000 to transform one room in your home—what room do you pick and how do you upgrade it?
What’s the most fascinating fact or piece of trivia you know?
If a tourist wanted an authentic experience of your hometown, what would you have them do?
How skilled are you when it comes to fixing things around the house?
Which movie perfectly captures the essence of the decade it was made in?
What’s the single most meaningful or impactful thing you’ve accomplished so far in life?
What’s your favorite memory from a family trip or vacation?
What was the last movie that genuinely made you tear up or cry?
What’s something a movie could do that would instantly make you leave the theater?
What movie quote do you think is overused and needs to be retired?
Which language do you find beautiful or fascinating, even though you can’t speak it?
What are some funny or clever euphemisms you’ve heard for ordinary activities?
Was your childhood better or worse compared to others growing up in similar circumstances?
What’s a fun experience you had once but have no desire to ever repeat?
How do you define true friendship, and what does it mean to you?
When was the last time you heard or saw something so ridiculous you thought it had to be a joke?
What movie do you think would be even better if the entire plot was played in reverse?
If you could be the best in the world at one thing, what would you choose?
What’s a habit or trait you tend to judge others for, even though you probably shouldn’t?
What’s a hobby or activity you’ve avoided because of its toxic or overly negative community?
What’s a topic or trend you’re completely sick of hearing about?
What’s something you’ve been holding in that you really need to vent about?
What activity or hobby are you “too old” for but still love doing?
What’s something you thought would be great but turned out worse than expected?
What do you think is the biggest historical blunder of all time?
What’s the most bizarre or unexpected hobby you’ve ever heard of?
What’s a boring sport or game that you think could be improved with some creative changes?
What’s legal today that you think will be outlawed within the next 10 to 20 years?
What’s the most unpleasant thing you’ve ever tasted?
What state or city have you always wanted to move to and why?
What do you think is the most common complaint people in your country have?
What’s something people romanticize that, in reality, isn’t as great as they think?
If you could be the world’s top expert in any niche, which would you choose?
If you built the ultimate treehouse, what would it look like, and what cool features would it have?
What’s a small regret that occasionally crosses your mind?
What’s something you loved that never became popular or ended too soon?
If there were an Olympics for ordinary people, what kind of events should they include?
If you had unlimited time to master any skill, which skill would you choose?
What’s the first thought that usually pops into your head when you wake up in the morning?
What websites did you use all the time but eventually stopped visiting?
What’s the most serious injury you’ve ever had, and how did it happen?
If there were a disease named after you, what would its symptoms be?
What would be the most inconvenient or terrifying phobia to have?
What’s a common spice or ingredient you absolutely can’t stand?
Who or what will always be a top priority in your life, no matter how busy you are?
What small or trivial things do you constantly find yourself worrying about?
What’s a food or drink that always looks more delicious than it actually tastes?
What’s the most valuable skill you’ve learned that’s been incredibly useful?
Which celebrity do you think would make the absolute worst dinner guest?
If you could choose any genetic modification for yourself, what would it be and why?
What life stories do you plan on sharing with your kids someday?
What’s one of the most memorable places you’ve traveled to, and why was it special?
What’s the biggest or most dramatic scene you’ve witnessed someone create in public?
What fictional “hero” is actually more of a villain when you think about it?
What’s something you’re shocked that no one has invented or figured out yet?
Describe your perfect burger—what’s on it and what makes it amazing?
What animal would make the ultimate pet if you could have any without limitations?
What’s one new thing you learned this week that you didn’t know before?
What three events have shaped you into the person you are today?
Have you ever had an experience that you just can’t explain, like something paranormal?
What’s a subject you’ve accidentally become an expert in?
Would you ever take a solo trip to a foreign country, and if so, where would you go?
What’s a selfless act someone has done that made a major impact on your life?
Who’s the funniest actor, actress, or YouTuber currently creating content?
What’s the weirdest or most unexpected thing you’ve seen while driving?
What’s a questionable decision you made that actually turned out great?
What do you often daydream about when you let your mind wander?
What’s a habit or behavior you find annoying in others but occasionally do yourself?
What was your all-time favorite cartoon as a kid, and why did you love it so much?
What two passions drive you the most in life?
How many phones have you accidentally broken or lost over the years?
What thoughts cross your mind when you see a homeless person on the street?
Which celebrity would be a total disaster as a country’s leader?
What signs do you notice that hint someone is destined for success?
What double standard needs to be eliminated immediately?

Personal questions to ask a guy

What memory or thought always stirs deep emotions within you?
If you could spend the day at a museum, would you choose art, history, or science?
When was the last time you experienced full-on panic, and what triggered it?
What’s your favorite emotional or tear-jerking scene from a movie that always gets to you?
Who do you feel most at ease spending time with—your significant other, family, or friends? Why?
Where’s your go-to spot when you need a break from the world?
What’s a deal-breaker for you when considering a long-term partner?
When you encounter a homeless person asking for money, how do you usually respond?
How often do you feel like life is moving faster than you can handle?
What activity or habit helps you feel completely relaxed and at peace?
How engaged are you in political discussions or social activism?
Who inspires you, and what traits do you admire about them?
What part of your life feels like it’s thriving, and which area could use a little boost?
What fact do you find uncomfortable but hard to forget?
What’s something your family did while you were growing up that seemed normal then but feels strange now?
What’s an opinion you hold that most people would find surprising or divisive?
Who in your life tends to stress you out, and who do you turn to when you need someone to ground you?
Is there a personality trait you’d like to improve or change? If so, what is it and why?
Which holiday was a big deal for your family growing up, and what traditions did you have?
What’s the most uncomfortable or awkward conversation you’ve ever had?
How daring are you when it comes to trying new things? What’s the most adventurous thing you’ve done?

Interesting questions to ask a guy

What’s the most impressive skill or talent you have that people are often amazed by?
What’s a job that doesn’t exist but the world could really use?
If you have kids, what career would you love for them to pursue, and what job would you prefer they avoid?
What’s the most valuable item you own, either sentimentally or practically?
What’s a popular movie that you somehow haven’t seen yet?
When was the last time you thought someone was on your level, only to find out they were way ahead?
If you were wrongfully imprisoned, how would you adapt to life behind bars?
What’s something that seems simple for others but is a real challenge for you?
What’s your ultimate dream job, and what makes it the perfect fit for you?
Which historical figure do you think was the most bold and fearless?
What’s a complex issue that people often see in black and white but actually has layers of nuance?
Which job would be your absolute nightmare, and why would you be terrible at it?
What news story do you think is being blown way out of proportion right now?
What book, movie, or TV show made you rethink the way you view the world, and how did it influence you?
What’s the most epic quote from a real person that sticks with you?
What’s one small change you could make today that would have a massive positive effect on your life?
What’s something that people take way too seriously but really shouldn’t?
Which college major do you think is the least practical?
What’s the next big trend or innovation you see on the horizon?
What commercial made you so turned off that it convinced you not to buy the product it was advertising?
If a movie were made about your life, what event would be its highlight?

Fun questions to ask a guy

Which movie desperately needs a sequel and why?
If your life were a movie, which songs would make up its killer soundtrack?
Which overused movie trope drives you absolutely crazy?
What “golden era” do you think we’re living in right now without realizing it?
If someone painted a portrait of you, what pose, outfit, and setting would you choose to reflect your personality?
What’s a game you totally dominate (or used to) that you’re proud of?
What’s the most ironically bizarre way someone could meet their end?
What unforgettable scene from a TV show has stuck with you forever?
The last meal you had is now your only food option for life. How long would you survive?
If coffee were outlawed, what would its underground street name be?
What’s the most hilarious or unexpected way you’ve ever gotten injured?
If you became a DJ, what would your signature DJ name be?
If you had to be an inanimate object for a year, what would you choose to be and why?
If you had a personal logo instead of a name, what would its design be?
Which TV catchphrase do you love to slip into everyday conversations?
You’re stepping into a fight scene. What epic song plays in the background to set the mood?
What’s the most unprofessional or shocking behavior you’ve witnessed at work?
What’s that one awful movie you can’t help but adore?
If you could secretly watch or listen to any location in the world, where would you place the feed?
What reality TV show concept would you create that the world absolutely needs to see?
What song instantly forces you to sing along no matter where you are?

Deep questions to ask a guy

Why do you think society still stigmatizes depression and mental illness despite growing awareness?
What are three jobs you think will be completely taken over by machines in the near future?
Will advancing technology save humanity, destroy it, or will it have a more neutral effect? Why?
What historical or hypothetical event would be so unbearable that you’d prefer not to live through it?
What defines a life well-lived, and what makes a life feel wasted?
What’s something that feels deeply disturbing or unsettling to you, even if others don’t see it that way?
When it comes to elder care, who should bear the primary responsibility: the government, families, or the elderly themselves?
Is human consciousness purely a result of brain activity, or is there something more beyond the physical realm?
What is the most meaningful purpose a person could dedicate their life to achieving?
Who is the one person in history you believe has had the most profound impact on the human race?
If every life were judged based on whether it made a positive or negative contribution to humanity, how would your life be measured?
Why do some people stay in toxic relationships even when they recognize the harm?
Should we screen infants for psychopathic tendencies? If so, what should society do with those identified as at risk?
Is poverty an unavoidable part of human society, or can it be completely eradicated?
Why do people often engage in self-destructive behavior despite knowing the consequences?
What experience or event has shaped your political beliefs the most?
Is morality something inherent in nature, or did humans invent it to govern themselves?
What common practices today will seem outdated, foolish, or even barbaric 100 years from now?
Is addressing income inequality necessary? If yes, what practical steps can be taken to close the gap?
What single action or policy could a government realistically implement to dramatically improve the lives of its citizens?
Do you think humans will evolve into something new, or will we cause our own extinction first?
What human characteristic is helpful in modern times but would have been a disadvantage in the distant past?
If you could design the ideal version of yourself, what qualities and traits would you have?
What prevents people from fully understanding who they are at their core?

Random questions to ask a guy

What book would you love to see turned into a blockbuster movie?
What makes you instantly assume a movie is going to be awful after watching its trailer?
What would be the most ridiculous thing to fill a piñata with?
What’s the coolest idea for a video game you could dream up?
What game would be hilarious to bring to life and actually play in the real world?
What’s the last thing you made from scratch?
Is there a conspiracy theory you secretly believe could be true?
What’s the most horrifying or nightmarish creature you could ever imagine?
What essentials would you include in a mental health first-aid kit?
What small behaviors make someone seem a bit creepy to you?
What story do your clothes tell about your personality?
If you were an animal, which one would best match your personality?
If you could sum up your life in a single image, what would that picture look like?
What’s the most fun or creative thing someone could have in their backyard?
Which movie star seems the most relatable or down-to-earth?
What would you rename your street if you had the chance?
What’s something you thought you were good at but later realized you weren’t?
If you had to break a world record to win $1 million, which record would you go after?
What are some songs you can sing word-for-word without missing a beat?
What’s the weirdest experience you’ve had while riding in a car?
What’s the wildest thing you could do with 400 pounds of cheddar cheese?
Who makes better meals, your mom or grandma?
Is there an app you can’t stand but still find yourself using every day?
What actor played a role so well that you can’t see them as anything but that character?
What villain in a movie or show do you secretly sympathize with?
What’s the most soothing or beautiful name you can think of for a baby boy or girl?
If the police raided your home right now, what item would look the most suspicious?
If you had to swap your hands for items already in your home, what would you choose?
What’s a song you’d actually pay money to never hear again?
What would you name the first human settlement on another planet?
What’s your favorite word based on how it sounds when you say it?
What’s the funniest or coolest phone case design you’ve ever come across?
If the internet held an Olympics, what events or “sports” would be featured?
What piece of technology never fails to put a smile on your face?
What’s the most recent thing you repaired successfully?
What are three activities you would give a perfect 10/10 and happily do again?
What piece of clothing or accessory immediately makes you judge someone?
Is there a company or franchise you wouldn’t miss if it shut down tomorrow?
What’s your most ridiculous first-world problem?
What food looks amazing but tastes like a complete letdown?
If you were forced into a duel, what weapon would you choose to defend yourself with?
Who’s the unluckiest person you know?
Could you survive a month in the wilderness with just basic tools?
What’s a skill or activity you’re bad at but secretly glad you don’t have to be good at?
What’s something you can’t buy online, no matter how much you search for it?
What’s the most stuffed or overly full you’ve ever felt after eating?
If you started your own magazine, what would it be called, and what would it feature?
What’s the perfect temperature to keep your home at for maximum comfort?
Which musical artist do you think gets way more attention than they deserve?
What’s your nightly routine before heading to bed?

Weird questions to ask a guy

What’s a win you had that came with such a cost, you questioned whether it was worth it?
What’s the worst experience you’ve ever had at a fast-food restaurant?
Which board game always turns into a heated argument or ends in disaster?
What’s the most iconic or quirky thing your hometown is famous for?
What’s the longest stretch of time you’ve gone without sleep, and what kept you awake?
What’s a piece of knowledge you wish you could erase from your memory?
What’s your go-to signature meal that never fails to impress when you cook it?
Where do you see the future of dating heading—apps, AI, or something unexpected?
How often do you find yourself doing tasks without really thinking about them?
What’s a task or activity that you find unbearably dull and tedious?
What movie, book, or show do you know tons about even though you’ve never watched or read it?
What futuristic piece of technology do you hope gets invented during your lifetime?
If you woke up 13 years in the past as your younger self but with all your current memories, what’s the first thing you’d do?
What’s one experience you’ve had that you’d strongly advise others to avoid?
Besides money, what’s something you always seem to be running low on?
If your computer crashed, what’s the one file you’d be devastated to lose?
What fun childhood activity do you think has been ruined or lost in today’s world?
What game can you play that turns you into an unbeatable champion?
What movie scene left a lasting mark on you in the most disturbing way?
What’s the most practical or valuable piece of advice your parents have ever given you?
What old-school way of doing things do you think is actually better than today’s methods?
When did you experience a moment where “looks can be deceiving” hit hard?
If you could upgrade one part of your body with a high-tech mechanical version, what would you choose?
What meaningful spot from your childhood no longer exists, and what replaced it?
If you could plan the most extravagant, over-the-top funeral, what would it look like?

Table of Contents