So you want to get a conversation started? That’s great!
There’s lots of different ways to start an interesting conversation with people – and I’ve found that the best way to do it is to simply be genuinely interested in what the other person is all about.
When you can find a genuine interest in other people, they’ll reward you by opening up and sharing all kinds of stuff with you – because everyone loves a good listener, and an interested listener is the best listener of all.
This is a list of some amazing ways to start a conversation with anyone you want – organized by subject, with a ton of random ones thrown in as well. You don’t have to start at the top – just scroll around until you find one that’s interesting to you!
You can use this to start a conversation with the person you want to talk to, or with a group of people, or however other way you want! I’ve found that a super fun way to use this list is to grab it on your phone and then pass it around a group of people, with everyone picking the question that’s most interesting to them.
Remember – genuine interest is the best way to have a deeply interesting and stimulating conversation. If you’re getting off the topic of the question – that’s good! It means you’re heading towards deeper waters and deeper conversation.
Just scroll through this list until you find a question that’s interesting to you! There’s even more questions than just [whatever number we pick at the end] , so you’re spoiled for choice towards finding the one that tickles your brain and makes you curious about the people you’re with!
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The Best Random Conversation Starters
Are you a spring, summer, fall, or winter person?
If you’re being honest, how often are you awake after 2:30am?
What do you consider to be the grossest habit that some people have?
Are you super organized in your personal life or do you prefer being messy?
If you get afraid when you’re in the dark, what do you picture is waiting for you there?
What’s your number one dream to check off the bucket list before you die?
If your life could be like one tv show, which would it be?
What were your favorite shows to watch as a kid?
Have you ever been in real danger, and has anyone rescued you from something really bad?
Which would you rather have – an awesome car or an awesome house?
What’s your biggest guilty pleasure when you need to unwind?
ok – you have an intro theme song to your life. What is it?
Who’s the person in your life that makes you the happiest?
What are your plans for the weekend, or are you just looking forward to relaxing?
If you’re stressed out, what do you do to relax and let go?
Do you have a tattoo? If not, do you ever think you’ll get one?
What’s the place you spend the most time during the day?
Tell me about the weirdest dream you’ve ever had?
What do you think determines success in the world – and who’s the most successful person by that measure?
What were you super into when you were younger that you’re not as into now?
All time best comedy tv show – which one is it?
What’s something that’s happened in your life that you just can’t explain?
Are you afraid of something that you know is super irrational?
What’s the most beautiful place you’ve ever visited?
What do you check to make sure you have on you every time you leave the house?
About how long do you spend on the internet every day – and what’s your rotation of what to do?
Where’d you go on your last vacation? Why?
What’s your favorite thing about school/work?
Who’s your favorite entertainment artist – like an actor or a musician?
Do you always like to get things done or do you like to relax when you have free time?
Are you still best friends with the person you were friends with in elementary school? Who was it?
When you’re hanging out with your friends, what is it that you’re most likely to be doing?
Do you get nervous speaking to a group of people? Have you ever done it?
Who’s the most important person in terms of making you into the person you are today?
You get to change your name without having to make everyone learn the new one – what’s the name you pick?
You get to answer one question about what’s going to happen in the future – what’s the question and why?
If you had to pick one period in your life to get to do over again, which do you pick?
What do you think is the one thing you’re best at?
Where in your house do you prefer to hang out?
You only get to watch one show that’s currently on tv – what is it?
Are you into reality tv? Why or why not?
What’s your tv watching style? Do you binge watch shows or ration them out?
How do you feel about pets? Do you have any?
What’s your go to video online to make people laugh?
What was the last project you put 100% effort into making it the best it could be?
What’s your favorite possession that you own? What’s the most useful?
What’s your biggest pet peeve in terms of a habit that someone else has?
Pick the 3 words that describe you the best – why did you pick those?
You get to pick one insect or animal to make extinct immediately – which do you pick, or would you pick any at all?
What forgotten phrase or slang do you think should make a comeback?
Do you curse? Why or why not?
Who’s someone we know that you admire – and why do you admire them?
All time funniest tv comedy series – what you got?
What’s your weirdest, most useless talent? Let’s see it!
What’s the best present you’ve ever gotten on your birthday or otherwise?
If you were going to start a business yourself, what would you pick to do?
What’s the most controversial opinion you hold?
What’s your least favorite place you’ve ever lived?
When you hang out with your group of friends, what do you bring to the table?
What’s your go to thing to do when you’re feeling crappy to help yourself feel better?
What’d you do last weekend? Did you go anywhere?
What’s your preferred way to waste time?
You get any animal to have as a loyal pet – what’s the animal you pick and why?
What’s something that’s gone really mainstream that you really don’t like?
Describe your perfect weekend – where are you and what do you do?
All time favorite number, you only get one – what is it?
When was the most beautiful sunset you’ve ever seen, and where did you see it?
Do you have a go to place for beautiful scenery near where you live?
What’s your go to first date – the one you save for people you really like?
What’s your biggest seemingly normal thing that makes you feel nervous?
Alright – who’s the person you’d least like to be stuck on an elevator with, and the person you’d most like to be stuck on an elevator with?
You get one show that’s been cancelled to bring back with the same cast and writers – which do you pick and why?
Are you more of a jeopardy person, wheel of fortune person, or price is right person?
What’s your most recent obsession – and why does it hold your interest so well?
Who’s the friend you’ve had the longest? Are you still close?
What’s something in the news that you’re following closely?
Do you have any smells that are inextricably linked to great memories you have?
Do you volunteer or do anything else to help people in your free time?
What’s the weirdest thing that you think otherwise normal people believe?
Top underrated tv show of the last 20 years – which one is it?
What’s the one thing that other people don’t mind but that drives you insane?
The Best Music Conversation Starters
What’s your all time favorite band, and why?
What was the first band you ever really loved? Do you still like their music?
What’s the one album that you couldn’t live without?
You’re stranded on a desert island and can only pick 3 bands worth of music to bring – who do you pick?
What’s the last song that you hit play on?
What’s your ideal workout music?
How do you find new bands to listen to?
What’s your favorite soundtrack to a movie or game?
What’s your favorite medium? Digital, records, cds, tapes – what do you like most?
Are you into classical music?
Are you more into pop, or obscure music, or somewhere in between?
Do you like seeing bands live?
What’s your favorite concert you’ve ever been to?
What’s the song that’s guaranteed to make you feel emotional?
What’s your go to song when you need to get into a better mood?
What’s your favorite band right now? Why do you like them?
What’s your favorite genre of music? How would you convince a stranger to listen to that type of music?
What do you think was the best decade for music – including this one?
The Best Phone Conversation Starters
Are you addicted to your phone? Do you feel incomplete when you don’t have it on you?
What do you think phones will look like a decade from now? What kind of features would they have?
What’s the one thing you wish your phone could do that it can’t do right now?
If you forgot your phone, how far from your house would you have to be before it wasn’t worth it to go back and get it?
Are you someone who likes to text people or call people?
When did you get your first smart phone?
What’s the one thing about your phone that annoys you the most?
Do you use a case for your phone? How good is it?
How often do you feel like your phone vibrated when it really didn’t?
Do you like to upgrade your phone every time a new one comes out or do you wait?
Do you check your phone all the time, or only when you feel it ring or vibrate?
How long have you had your phone number?
The Best Food Conversation Starters
You can only eat one food for the rest of your life – what is it?
What’s the one food you absolutely can’t stand and don’t want anywhere near you?
What’s the grossest looking food you think is delicious?
Are you a buffet person? Or do you prefer to order from a menu?
Have you ever been in a real life food fight before?
If you were going to get the death penalty tomorrow, what’s the last meal you order for dinner tonight?
What are your grocery list staples? What can you not live without?
The big question: do you prefer cake or pie?
Are you more of a cookie fan or a brownie fan?
Are you into spicy food or do you like food that isn’t spicy?
What’s the spiciest food you’ve ever eaten?
What’s your guilty pleasure food – you know it’s bad for you but you can’t stop eating it?
Would you rather get rid of pizza forever or burritos forever? Why?
What’s the best dip? Guacamole? Salsa? Queso? Something else?
What’s one food you completely don’t understand the appeal of?
Which flavor do you like more, sweet or salty?
All time favorite type of apple – what’s your favorite?
The Best Life Goal Conversation Starters
What’s the number one thing on your bucket list that you absolutely have to accomplish?
What’s more important to you – career, family, creative dreams or something else?
Are you a person who likes to set goals or do you more go with the flow?
When you think about your future, what kind of picture do you envision?
When do you want to retire? How are you working to make that possible?
Are you someone who sets goals then accomplishes them, or do you jump from thing to thing and use your goals to motivate yourself?
What do you want to accomplish in the next year or two? What’s the biggest thing you want to see happen in your life?
Do you have any goals about changing the world or changing society? How about on a local level?
What impact do you think your parents have had on the things you want to achieve in your life?
What are your goals specifically for yourself? How about in the next 10 years?
Do you want to eventually own a house?
What’s the goal that you’ve achieved that you’re the most proud of in your life?
Have you ever completely failed to accomplish a goal you set for yourself? What happened?
As you’ve gotten older, how have your goals and priorities changed?
The Best Travel Conversation Starters
Do you want to travel in your life, or are you happier staying where you are?
Have you ever been to another country? Did you like it?
What’s your favorite place you’ve ever traveled to?
If you could pick one country in the world to travel to, which one would you pick and why?
Do you have any travel plans? Where are you going to go?
Would you rather travel during a vacation or stay home and relax?
What’s your favorite part about traveling and seeing new places?
If you’ve done lots of traveling, do you think it’s changed who you are? Why or why not?
Are you someone who likes to travel in a group, or are you more of a solo traveler?
When you travel, do you like to follow the recommendations in a guide book or blaze your own path?
What’s the worst place you’ve ever stayed when you’re traveling? What about the best?
Have you ever been on a super long plane ride? What did you do to keep from getting bored?
Who’s your favorite person that you ever met while you were traveling?
Have you ever been somewhere that you thought was completely overrated? Where was it?
What’s the most relaxing place you’ve ever traveled to?
What’s the travel destination with the most beautiful scenery that you’ve ever visited?
What’s your favorite city that you’ve ever visited? Why?
Do you prefer to travel by plane? Or road trip in a car? Bus? Train? Why?
When you travel, do you like to go to somewhere warm, or do you not take climate into account?
Do you prefer to visit places with beaches or places with museums and culture?
What’s your favorite food you’ve ever eaten while traveling?
The Best Holiday Conversation Starters
What’s your favorite holiday during the year? Why?
You get to pick one holiday food – like easter eggs, eggnog at Christmas, thanksgiving turkey, or something else – which do you pick?
What’s your favorite fact about a holiday that not many people know?
What’s your favorite thanksgiving food?
Does your family celebrate any holidays? Which ones are the most important?
If you could make a holiday out of thin air, what would you create? What would it be about? What would the traditions be?
Do you dress up on Halloween or stay home and hand out candy?
Pick one out of Christmas, thanksgiving, Halloween, and new year’s eve/day – which one do you get rid of and why?
Do you like Valentine’s Day? Or do you think it’s dumb?
Do you send holiday cards to people over the winter holidays or not? Do you get any?
What’s your all time favorite holiday dessert?
The Best Fashion Conversation Starters
Are you someone who plans out their outfits or just puts on whatever you feel like?
Do you follow fashion? Or do you not care?
What’s the shirt that’s been in your closet the longest? How did you get it?
Do you buy lots of shoes? Or do you stick to one pair and wear them out?
What’s your all time favorite shirt that you’ve ever owned?
If no one would look at you funny, what’s your dream outfit that you’d wear?
Do you look at magazines and videos in order to plan an outfit, or do you buy whatever you feel like?
What’s a fashion trend you think is making a big comeback?
What’s your go to outfit when you just want to be comfortable and relax?
What kind of pajamas do you wear to bed?
What’s your favorite type of clothes you like to see someone you like wearing? What kind of outfits are you most attracted to?
The Best Time Of Year Conversation Starters
What’s your favorite season? Why?
Do you like warm weather or cold weather? Or does it not matter to you?
If you could live anywhere you wanted, in any climate you wanted, what would you pick?
What’s your favorite thing to do on a rainy day?
Which season has the best holidays? Why?
Do you have a particular season you like to take vacations during?
Did your family ever take trips when you were younger? When did you take them?
Would you rather it be really really hot outside or really really cold outside? Why?
Do you like it when it snows?
Would you rather live somewhere where the climate is the same year round, or do you like when the seasons change over the course of a year?
What’s your favorite thing about spring? What do you like to do most in the spring?
What’s your all time favorite thing to do in the summer?
Do you prefer the kind of things you get to do in the winter or the summer?
What’s your all time favorite drink to warm up on a cold winter day?
What’s your favorite fall activity to do?
The Best Random Conversation Starters
If you could choose to be immortal, would you say yes? Or no? Why or why not?
Would you rather be a spaceship or a volcano?
What would you do if you could fast forward or rewind time at will, and what would you do if you could pause time?
If you had an arch-nemesis, what would they look like? What would they do?
What’s your all time fantasy flavor of ice cream?
Pretend your mind is a castle. What does the castle look like? What does it have in it?
What kind of animal would you be if you could be any animal in the world?
Would you rather be able to fly like a bird or breathe underwater like a fish?
If you had the opportunity to take a one way journey into another (habitable) world, but you didn’t know what was on the other side – would you go?
If you could have dinner with anyone, alive or dead, who would you choose and why?
Would you rather have the ability to fly or to read minds?
You get to pick one superpower – what is your superpower and how would you use it?
You get to pick one person in the world to be the president of the United States – who’s the worst choice you could possibly make? Who’s the best?
The Best Sports Conversation Starters
What’s your favorite sport to play? What’s your favorite sport to watch?
Did you grow up rooting for sports teams? Why did you pick them in particular?
What do you think is the hardest sport? What’s the easiest?
How often do you typically watch sports?
If you could be a professional athlete – which sport would you pick and why?
Do you think poker is a sport? How about darts? Skiing?
What’s the most exciting sporting event you’ve ever watched?
What’s your favorite sporting event you’ve ever been to?
Has any team you grew up rooting for ever won a championship? What were you doing when they won?
You can guarantee your favorite team a championship this year, but for the next 10 years they’re absolutely terrible. Do you do it?
Who’s your all time favorite athlete? What about favorite athlete by sport?
Do you like to play sports? What’s your favorite sport to play?
What sport do you wish you were amazing at?
Have you ever gotten hurt playing a sport? How long did it take to recover?
The Best Science And Technology Conversation Starters
If you could pick one invention to be invented today – what would you pick and why?
Do you think humans will ever invent anything that makes time travel possible?
What do you think will be the biggest invention in the next 25 years? What about 10 years? 5?
Do you think technology makes our lives better or worse? What about simpler or more complicated?
What sci-fi movie do you wish was real?
If you had to travel 300 years back in time, and could only bring one piece of technology, what would you pick and why?
Do you think the world will look mostly the same 10 years from now or completely different? How about 5 years from now?
What’s the possibility that you’re most excited about for the future?
What technology do you think has the most potential that’s being developed right now?
What technology or discovery do you think changed the world the most all time? What do you think the next world-changing piece of technology will be?
What’s your personal favorite invention of all time?
What scientific advancement or technology do you personally think has been the worst for the world? Why?
The Best School Conversation Starters
What was your favorite class you ever took? Your least favorite?
Who was your favorite teacher? What made them so great to you?
What do you think of schools teaching classes online? Do you think it’s good or bad?
Do you think you would ever homeschool your kids if you have them? Why or why not?
Do you think that public schools are doing a good job? Why or why not?
Did you like gym class when you were younger or did you dread it?
What subject did you dread the most across all your years of school?
What was the easiest subject you took that you just were able to do naturally?
Did you ever have a teacher or a guidance counselor that changed your life? How did they do it?
What’s the worst you’ve ever done on a test or a paper?
Do you procrastinate when you have a big project due, or do you do it in advance so that you don’t have to worry about it?
The Best Book Conversation Starters
What’s your all time favorite book? Why?
Do you prefer to reread your favorite books, or to read new books?
What’s a book that you could read over and over and not get tired of? What book have you read the most?
What’s the last book that you read? Did you like it?
Who’s your favorite author? Why are they your favorite author?
What’s your favorite genre of book? What about your second favorite?
Do you like to read fiction, or do you prefer nonfiction books?
Are you a fast reader, or do you like to read carefully and absorb everything you read?
Do you get your books from the library? If not, where do you get them?
Have you ever read on an e-reader like a kindle? Did you like it? Do you prefer it to a regular book?
Do you like to build up a library of books in your house, or gift books that you’ve read away to your friends and family?
What was your favorite book growing up? Why? When was the last time you read it?
Did you ever read a book that changed your life? What was it and what kind of impact did it have on you?
What’s the biggest and thickest book you’ve ever read all the way through?
Are you the type of person who has to finish every book they start, or do you give up on books that aren’t holding your interest?
What’s the funniest book you’ve ever read?
What’s the saddest book you’ve ever read?
What’s the most influential book you’ve ever read?
What’s your least favorite book you’ve ever read? What about a book you were forced to read at school?
If you were banished to a desert island and could only bring 3 books, which books would you bring and why?
The Best Movie Conversation Starters
All time top 3 favorite movies – what are they?
What’s the worst movie you’ve ever watched?
Have you ever walked out of a movie theater before?
What’s the last movie you ever saw in theaters?
Do you still buy movies to keep at home? Or do you mostly stream?
What’s your favorite type of movie? Least favorite?
Do you prefer fictional movies or documentaries? Why?
Do you like scary movies or do they creep you out too much?
What’s your favorite snack to bring into a movie theater?
Have you ever snuck food into a movie theater? What about snuck into a second movie after seeing the first one?
What’s a movie that if you see it while channel surfing you have to stop and watch the whole thing?
When’s the last time you cried at a movie? What movie is guaranteed to make you cry?
Do you prefer to watch movies or read books? Why?
Do you like to go to movie theaters or watch movies at home?
Do you like to turn the volume up loud when you’re watching a movie?
What’s the movie that everyone told you that you HAD to see that you didn’t wind up liking very much?
What’s the weirdest movie that you’ve ever seen? Did you like it?
Want to find out if he really likes you? Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…