250+ Cool & Interesting Questions to Get to Know People Better

Deepen your bond with these fun and thought-provoking questions

Co-authored by Seth Hall and Bailey Cho

Last Updated: December 11, 2025 Fact Checked

• Cool Questions to Ask People
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• Guys
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• Girls
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• Friends
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• Family
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• Partners
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• Colleagues
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• Kids
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• Strangers
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• Yourself
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• Tips

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Looking to learn more about others and spark a great conversation? Asking cool questions is one of the best ways to build stronger bonds with people, whether you’re talking to friends, family members, colleagues, or strangers. That’s why we’re providing the ultimate list of cool and thought-provoking questions to impress everyone you know. Keep reading for funny, deep, and unique options!

The Coolest Questions to Ask Anyone

• What book or film changed your life?
• What kind of secret society would you start?
• If you owned a yacht, what would you name it?
• Would you rather never age physically or mentally?
• If you could fight any historical figure, who would it be?
• If you had to marry a cartoon character, who’s your spouse?
• If you could throw a party with an unlimited budget, what would it look like?

Steps

Section 1 of 10:

Cool Questions to Ask People

1. 
   Get to know someone better with these cool and creative questions. Whether you’re asking friends, family members, or complete strangers, there are so many cool questions to encourage vulnerability and prompt an interesting conversation. Here are some fun and engaging options to break the ice:

   • What could you write a book on?
   • What book or film changed your life?
   • What’s one dream you’ll never give up on?
   • What does your perfect sandwich look like?
   • What kind of secret society would you start?
   • What’s your ideal way to spend your birthday?
   • Who would play you in a movie about your life?
   • What’s your favorite thing about your hometown?
   • Would you rather never age physically or mentally?
   • If you could time travel, what decade would you go to?
   • Would you rather be able to control light or control sound?
   • If you woke up as an animal, what would you be and why?
   • If you could ask your future self one thing, what would it be?
   • If you could only see one color, what color would you choose?
   • What’s the most ordinary thing you find absolutely fascinating?
   • If you woke up tomorrow as a Muppet, what’s your next move?
   • Would you rather only be able to listen to old music or new music?
   • If you could only say one word for the rest of your life, what would it be?
   • If you could only wear one outfit for the rest of your life, what would it be?
   • If you could replace your hands with something else, what would you choose?
   • If you had to choose one song to describe your life right now, what would it be?
   • If your pet suddenly became human, what’s the first thing they’d yell at you about?
   • If you could make one thing socially acceptable that currently isn’t what would it be?
   • If you could invent a new ice cream flavor, what would it be called and what would be in it?
   • If you had to create a new holiday, what would it be about and how would people celebrate?
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Section 2 of 10:

Cool Questions to Ask Guys

1. 
   Ask about his personality, interests, and thoughts to deepen your bond. If you want to catch a guy off guard and show that you care about him, express interest in his personal opinions and preferences. Here are some funny, random, and insightful Qs to connect with any guy in your life:

   • Who was your first cartoon crush?
   • What’s your most-worn item of clothing?
   • What’s the best prank you’ve ever pulled?
   • What’s the craziest bet you’ve ever made?
   • If you owned a yacht, what would you name it?
   • How often do you think about the Roman Empire?
   • When’s the last time you felt a big adrenaline rush?
   • If you could fight any historical figure, who would it be?
   • If you could master one skill instantly, what would it be?
   • What’s your weapon of choice in a zombie apocalypse?
   • What’s an embarrassing song or band you secretly love?
   • If you could create a new sport, what would the rules be?
   • If you were a villain in a movie, what would your evil plan be?
   • If you were an Olympic athlete, what sport would you compete in?
   • If you could invite someone to be on your podcast, who would it be?
   • If your life were a video game, what cheat code would you use the most?
   • If your tongue had to taste like one food forever, what’s the worst choice?
   • If you had to scream a word every time you sneezed, what’s your battle cry?
   • If you woke up as a giant chicken tomorrow, what’s the first thing you would do?
   • If you were a superhero, what would your name, costume, and catchphrase be?
   • If you had to fight 1,000 second-graders or one MMA fighter, who are you taking on?
   • If your laugh got changed to a completely different sound effect, what would you choose?
   • If your reflection in the mirror started roasting you every morning, what’s the first thing it would say?
   • If your pet turned into a human version of themselves, do you think they’d be chill or try to fight you?
   • If you had to swap heads with one animal but keep your human body, which one would you choose?

Section 3 of 10:

Cool Questions to Ask Girls

1. 
   Throw out fun, open-ended questions for an interesting conversation. To start an engaging conversation with a girl, “ask open-ended questions that leave a lot of room for more than just a yes or no answer,” says dating coach and matchmaker Laura Bilotta. It’s a “fun way to get to know more about someone and will certainly break the ice.” Some topics you can talk about include her personality, hobbies, interests, and tastes:

   • What gives you the ick?
   • What’s your style inspiration?
   • What would you title your memoir?
   • What celebrity would you risk it all for?
   • What role do you play in your friend group?
   • What do you get the most compliments about?
   • What outfit makes you feel the most confident?
   • If your personality were a drink, what would it be?
   • If you could make a new dessert, what would it be?
   • What’s your opinion on large age gaps in relationships?
   • If you had to marry a cartoon character, who’s your spouse?
   • If you could swap voices with any celebrity, who would it be?
   • If you starred on a reality TV show, what would your catchphrase be?
   • If you could be best friends with any celebrity, who would you choose?
   • If you could swap noses with any animal, which one would you choose?
   • If you had a secret alter ego, what would her name and personality be like?
   • If you had to replace your legs with something random, what would you pick?
   • If you could make one weird law that everyone had to follow, what would it be?
   • If you could only speak in movie quotes for a day, what movie would you quote?
   • If you had to sit between 2 celebrities on a flight, who would you choose and why?
   • If you had to live in a house made entirely of one food item, what food would it be?
   • If you had a theme park based on your personality, what would be the wackiest ride?
   • If you had to name your kid after something currently in your fridge, what’s their name?
   • If your hair color changed based on your mood, what color would you be most of the time?
   • If you had to replace all your teeth with one type of tiny object, what would you choose?
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Section 4 of 10:

Cool Questions to Ask Friends

1. 
   Deepen your friendship with these cool and unique questions. Asking cool questions is a great way to pass the time and bond with your friends. You can think of random hypothetical situations or ask about their personality, unpopular opinions, or favorite celebrities. Here are some interesting questions to learn more about your friends:

   • What’s your most irrational fear?
   • What was your sexual awakening?
   • What’s your favorite form of potato?
   • What would you do during the Purge?
   • What’s a conspiracy theory you believe in?
   • If you could steal anything, what would it be?
   • What’s your toxic trait when it comes to dating?
   • What’s a hill you’ll die on, no matter how ridiculous?
   • What expensive thing is absolutely worth the money?
   • Do you think there’s anything worth killing or dying for?
   • What character archetype is closest to your personality?
   • If we formed a band, what kind of music would we make?
   • If you could change your name, what would you change it to?
   • If you were an inanimate object, what would you be and why?
   • If you could make a children’s TV show, what would it be about?
   • What’s the most savage roast you can come up with on the spot?
   • If you had to swap lives with a celebrity for a day, who would you choose?
   • If you could eliminate one word from existence, what would it be and why?
   • If you could throw a party with an unlimited budget, what would it look like?
   • If someone followed you and narrated your life, who would you want it to be?
   • If you could only eat one color of food for the rest of your life, what would it be?
   • If you had the power to completely eliminate one disease, which one would it be?
   • If you could form a band with 5 solo artists, dead or alive, who would you choose?
   • If you had to wear a Halloween costume for the rest of your life, what would you pick?
   • If you could have an unlimited supply of one thing for the rest of your life, what would it be?

Section 5 of 10:

Cool Questions to Ask Family

1. 
   Strengthen your family ties with these cool and insightful questions. No matter how long you’ve known someone, there’s always something new and exciting to learn about them. These cool questions will encourage your family members to open up and share new stories, helping you discover more about their lives than ever before:

   • What was your favorite toy as a child?
   • Where do you wish you had grown up?
   • What has been the best year of your life?
   • What’s the next dish you want to master?
   • What was your favorite series growing up?
   • What scent reminds you of your childhood?
   • What do you want written on your headstone?
   • What are 3 questions you’d like to ask our pet?
   • What’s the happiest moment of your life so far?
   • Has social media improved or impaired society?
   • If you could relive any memory, what would it be?
   • What’s a fear you’ve faced and how did you face it?
   • Who would you want to trade places with for a day?
   • What’s the biggest punishment you’ve ever received?
   • What historical event would you have liked to experience?
   • What’s the first thing you do after getting home from a trip?
   • Would you rather have your first child when you’re 18 or 50?
   • If we all turned into animals, which one would each of us be?
   • If you could be any age for one year, what would you choose?
   • Would you rather have a pause or a rewind button in your life?
   • If we were all in a heist movie, what would everyone’s role be?
   • If our family had to compete in a talent show, what would our act be?
   • Would you rather live in a world where there’s no crime or no privacy?
   • What’s the biggest mistake you’ve ever made that actually turned out okay?
   • In those first few seconds, are you hoping it’s “Ice Ice Baby” or “Under Pressure”?
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Section 6 of 10:

Cool Questions to Ask Partners

1. 
   Ask fun and deep questions to discover new sides of your partner. Looking for ways to strengthen your relationship and keep the romance alive? Ask your partner about their dreams, fears, favorite things, and more. It’s the best way to build emotional intimacy and understand them on a deeper level, which can improve your relationship in the long run. Here’s a mix of random and insightful Qs to help you get started:

   • In what ways are you stubborn?
   • What does your dream house look like?
   • What’s the hardest loss you’ve overcome?
   • If I had a warning label, what would it say?
   • Do you believe in astrology? Why or why not?
   • Would you still love me if I turned into a worm?
   • What’s the most selfish thing you’ve ever done?
   • If we had a Netflix show, what would it be called?
   • What’s your favorite thing about your hometown?
   • How would you approach me if we weren’t dating?
   • What’s something you’re too old to do but still enjoy?
   • What’s a random fact about you that I don’t know yet?
   • If our relationship had a theme song, what would it be?
   • Do you think physical or emotional pain is worse? Why?
   • If we were in a rom-com, what would our “meet-cute” be?
   • What’s a trait you admire in me but don’t possess yourself?
   • What’s a weird habit I have that you find secretly adorable?
   • If I had an identical twin, how would you know it’s really me?
   • What do you think makes our relationship unique or special?
   • If you had to describe me using 3 emojis, what would they be?
   • If we made up our own language, how would we greet each other?
   • If we could switch lives for a day, what’s the first thing you’d do as me?
   • If we had to survive on a desert island, who would lose their mind first?
   • If you could give your younger self relationship advice, what would it be?
   • If you could change one thing about your physical appearance, what would it be?

Section 7 of 10:

Cool Questions to Ask Colleagues

1. 
   Learn more about your colleagues with these quick and easy icebreakers. Whether you’re talking to new hires or people you’ve worked alongside for years, asking icebreakers is a great way to get to promote team building and improve workplace dynamics. Just ask questions about each other’s interests, preferences, and personalities, or come up with fun hypothetical scenarios about the office:

   • What’s your death row meal?
   • What’s been keeping you sane lately?
   • If our office had a mascot, what would it be?
   • What’s the most useless talent you possess?
   • What’s the fanciest event you’ve ever attended?
   • What’s the coolest project you’ve ever worked on?
   • Out of all your jobs, which has taught you the most?
   • What’s the most random thing you’ve Googled lately?
   • What’s the worst advertisement you’ve seen recently?
   • What’s your biggest non-work-related accomplishment?
   • If our team was a band, what would our band name be?
   • What’s the most interesting thing you’ve learned recently?
   • What would your occupation be if you lived 100 years ago?
   • What’s the best excuse you’ve given to skip school or work?
   • Would you rather work four 10-hour days or five 8-hour days?
   • What’s one thing you want to accomplish before the year is over?
   • What’s the most inappropriate time you’ve laughed at something?
   • Which team member would you nominate to join Mount Rushmore?
   • If you could bring one celebrity guest speaker to the office, who would it be?
   • If you had to work in an office made entirely out of candy, what candy would it be?
   • Would you rather take a month-long vacation or have an extra day off every week?
   • Would you rather get locked in the office overnight or accidentally lock your boss out?
   • If you could be a fly on the wall at any meeting at work, which one would you choose?
   • If you had a personal theme song that played every time you entered the room, what would it be?
   • If you could design a custom desk accessory that would make your life easier, what would it be?
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Section 8 of 10:

Cool Questions to Ask Kids

1. 
   Encourage kids to share their thoughts and feelings with these questions. Throw out questions about their likes, secret skills, or anything else you’d like to know. You could also come up with funny and creative scenarios to pick their brain and get them to use their imagination. Here are some great questions to ask kids:

   • Who’s your favorite movie villain?
   • What’s your favorite board game?
   • What’s the best color in the rainbow?
   • What would you do if you had 4 arms?
   • What instrument has the funniest sound?
   • What’s your favorite slang word or phrase?
   • If you were invisible, who would you spy on?
   • If it rained food, what would you want it to be?
   • What do you think goldfish think about all day?
   • If animals could talk, who would be the rudest?
   • What sound do you think a giraffe should make?
   • What’s the craziest thing you’ve done in school?
   • Who’s your favorite Disney character of all time?
   • If you were an adult for a day, what would you do?
   • If you could make any slime scent, what would it be?
   • If you were a clown, what would your clown name be?
   • If everything you drew came to life, what would you draw?
   • If you could be any mythical creature, what would you be?
   • If the floor was lava, how would you get from place to place?
   • If you were a mad scientist, what would you invent and why?
   • Would you rather talk like Yoda or breathe like Darth Vader?
   • If you could get rid of one vegetable forever, what would it be?
   • If aliens abducted you, what’s the first thing you’d say to them?
   • If homework didn’t exist, how would you spend your extra time?
   • If you could live in any fictional world, which would you choose?
   • Would you rather sleep on a mattress made of jello or warm soup?

Section 9 of 10:

Cool Questions to Ask Strangers

1. 
   Ask interesting questions to break the ice and bond with anyone. If you’re talking to someone you’ve just met, asking cool and creative questions can help you learn more about them (without making things awkward). Some topics you can bring up include their personality, hobbies, interests, and tastes:

   • What’s your most prized possession?
   • What makes your day instantly better?
   • What do you usually daydream about?
   • What’s one food that should be banned?
   • Do you think money can buy happiness?
   • What’s your idea of the perfect vacation?
   • What do you miss most about being a kid?
   • What’s the best song to blast on a road trip?
   • What’s the weirdest gift you’ve ever received?
   • What’s the closest you’ve ever come to dying?
   • What’s the most beautiful view you’ve ever seen?
   • Would you rather have more time or more money?
   • What’s the most memorable meal you’ve ever had?
   • What’s the funniest thing you believed in as a child?
   • What’s the nicest compliment you’ve ever received?
   • What’s the strangest superstition you’ve ever heard?
   • What’s the best thing that happened to you this week?
   • What’s your reason for getting out of bed in the morning?
   • What’s the most useful thing you’ve learned from traveling?
   • What’s the weirdest thing you’ve seen in someone’s house?
   • How would you summarize your life so far in a single sentence?
   • Would you rather know the cause of your death or the date of your death?
   • If you could go back and change one decision in your life, what would it be?
   • What’s something you’ve done that you recommend everyone does before they die?
   • Would you rather be more attractive than your partner or have your partner be more attractive than you?
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Section 10 of 10:

Cool Questions to Ask Yourself

1. 
   Increase your self-awareness with these deep and revealing questions. Curious about why you think and act the way that you do? Consider answering these questions in a journal to learn more about your values, goals, and motivations:

   • What makes me jealous?
   • Where is my happy place?
   • What’s my personal mantra?
   • What’s holding me back in life?
   • What brings out my inner child?
   • When do I feel the most beautiful?
   • Who do I compare myself most to?
   • What makes me smile on a bad day?
   • What do I want to stop apologizing for?
   • What did I learn about myself this week?
   • How has my confidence increased with age?
   • What’s the biggest misconception about me?
   • Who in my life deserves the biggest thank you?
   • What would I never want to change about myself?
   • What’s my favorite thing about the age I am today?
   • What mistake of mine taught me the most recently?
   • What belief about myself is holding me back the most?
   • Who inspires me to become a better version of myself?
   • What am I proudest of myself for saying “no” to recently?
   • What current events or causes am I most passionate about?
   • Do people tend to overestimate or underestimate me? Why?
   • What do I want to learn more about in this chapter of my life?
   • If my life were a book, what’s the title of the chapter I’m in now?
   • When was the last time I pushed myself out of my comfort zone?
   • What’s a “flaw” I’ve learned to appreciate about myself over time?

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Tips

• If someone doesn’t feel comfortable answering your questions, Bilotta says to “respect [their] boundaries and move on.”
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