Whether we are just starting to get to know someone we are dating with the hope that it will lead to a relationship, or whether we are making small talk at a party or event, knowing what to say can be a little tough. I mean, do you really want to talk about the weather for 20 minutes again? The answer to that is probably not!

All the same though, the weather and other small-talk/chit-chat questions often seem like the easiest thing to grasp for when you are chatting to someone you don’t know very well. What if there was a sure-fire way to make small talk that little bit more interesting though? We may just have a solution for that!

We have developed a huge list of questions for you to keep in your mental repertoire to make sure that no conversation ever gets dry and boring again. It will help you make small talk a thing of the past and make you seem very interesting (and interested) for asking such fascinating and engaging questions. Are you intrigued yet? We bet you are!

As well as being great for getting to know new people in your life, some of these fun questions can also be used in get-togethers with your loved ones as they are sure to spark some friendly debate, especially the ‘this or that’ questions. We also have a section about ‘unpopular opinions’ that would be a hoot for college parties or sleepovers.

Whatever the reason you need some fun questions for, we have got your back.

Quick Guide: Fun Questions to Ask

Here is our ginormous list of some of the most fun questions to ask. We decided we should split the questions into sections so that you can find areas that are relevant to you and the person you are talking to. In our list you will find sections dedicated to ‘favorites’ questions, ‘would you rather questions’, and so much more.

Introductory Questions

  1. What’s your name?
  2. How old are you?
  3. Do you live locally?
  4. What is your job?
  5. Do you have a family?

These super simple introductory questions are definitely something we don’t need reminding of. Whenever we meet someone for the first time we always tend to ask questions like this.

Nevertheless, they are super important and they allow you to test the waters with the person you are having a conversation with before diving into the more fun questions. What we mean by this is that not everyone will tell you with ease the answer to some of the more personal or random questions if there hasn’t been a form of introduction first.

What’s your favorite….?

  1. What’s your favorite pizza topping?
  2. Do you have a favorite animal? What is it?
  3. What’s your favorite season?
  4. Who is your favorite singer?
  5. When it comes to ice cream, what flavor would you pick as your favorite?
  6. What is your favorite color?
  7. Who is your favorite character from Friends (or any other TV show you have seen)?
  8. What’s your favorite holiday?
  9. Do you have a favorite pen that you write with? Why?
  10. What is your favorite soda flavor?

Asking someone these ‘favorites’ questions allows you to get to know them that little bit better. They will likely enjoy telling you about their favorite things and elaborating on them when the conversation, undoubtedly, starts to naturally flow.

Music-related questions

  1. If you could see any singer or band that is no longer alive, who would it be and why?
  2. Do you enjoy listening to chart music?
  3. Who is the best artist or band you have ever seen live?
  4. Who is the worst artist or band you have ever seen live?
  5. Do you remember the first record, tape, or CD you ever bought? Who was it?
  6. Do you have any concerts or gigs that you are attending coming up soon?
  7. Do you need music playing in the background when you drive or do you prefer silence?
  8. When was the last time you listened to a CD or record in this music-streaming era?
  9. What album do you have on repeat right now?
  10. Do you play an instrument or sing well?

Most people enjoy music, and talking about music with someone tends to be an excellent starting point for forming a bond. This is especially true if you find you have some things in common.

Food questions

  1. What was the last meal you ate?
  2. What is your favorite independent restaurant?
  3. What is your favorite chain restaurant?
  4. Do you have a favorite ‘comfort food’ that makes you happy even when you are really sad? What is it?
  5. How do you take your coffee?
  6. Do you have any food allergies or dietary preferences?
  7. Would you ever go vegan?
  8. Does pineapple on pizza offend you? How about anchovies on pizza?
  9. What cuisine is your favorite?
  10. Do you enjoy baking?
  11. What is your ‘go-to’ recipe that you make when you are having company over for dinner?
  12. What condiment can you not live without?
  13. Ketchup or mustard on a hotdog? Or both?
  14. What do you think is the messiest food to eat?
  15. Do you spill food down yourself a lot?

Food is excellent common ground between everyone. Finding out more about your conversation companion through a shared love of food is always a good idea. As they say, food is the key to the heart.

Book and literature questions

  1. Do you prefer a physical book or an e-book? Perhaps even an audiobook?
  2. Would you call yourself an avid reader?
  3. Do you read as much as you’d like to?
  4. What was your childhood favorite book?
  5. What fictional character from a book would you most like to meet and why?
  6. If you could be transported into any literary universe where would you choose?
  7. What is the worst book you have ever read?
  8. What book does everyone love that you cannot stand?
  9. What book does every hate that you adore?
  10. If money was no obstacle, would you get a huge library in your house?
  11. What Harry Potter House are you in?
  12. Were you (or are you) Team Edward or Team Jacob?
  13. If you could switch lives with a character from a book who would it be?
  14. What book are you currently reading?
  15. What book was the biggest surprise for you?
  16. What book was the worst disappointment for you?

Okay, granted not everyone is as avid a reader as us, but we have always found that chatting about books is a great way to get to know someone. Even if they are not a self-confessed bookworm, some of these questions may still be of interest to them, and they can easily be adapted to film or TV questions, too.

Would you rather….?

  1. Would you rather be chased by a dog-sized wasp or a cat-sized bear? (both sound scary!)
  2. Would you rather never eat your favorite food again or never listen to your favorite singer again?
  3. Would you rather have the ability to talk to animals or have the ability to communicate with ghosts?
  4. Would you rather have the ability to read minds or have super speed?
  5. Would you rather have the ability to turn invisible or the ability to freeze time?
  6. Would you rather have the ability to control the weather or the ability to time travel?
  7. Would you rather have an elephant’s trunk on your face or have gills and fins like a fish?
  8. Would you rather have the ability to speak any language in the world or have a photographic memory?
  9. Would you rather have scales all over your body or fur all over your body?
  10. Would you rather have the ability to sing really well or dance really well?

‘Would you rather’ questions are always a fun conversation game to have with someone. It enables you to really get to know them and see how they answer some impossible choices!

Philosophical questions

  1. Do you believe in life after death?
  2. Do you believe in fate?
  3. Can we control our destiny?
  4. Why do you think we exist?
  5. Do you believe in extraterrestrial life?
  6. Do you think there are alternate universes?
  7. Do you believe in the law of attraction?
  8. Do you believe it’s nature or nurture that determines how a person is?
  9. Is suffering a necessary part of human life?
  10. Do you believe in soulmates?

Some of life’s most difficult questions are philosophical ones. They make for a great topic for debate as well as being an interesting window into the mind of your companion.

Questions about their childhood

  1. Was your childhood a happy one?
  2. As a child, what was your favorite food?
  3. Looking back to your childhood, can you remember if you had a favorite person, whether that be a family member or best friend?
  4. What advice would you give a 5 year old you?
  5. What advice would you give a 10 year old you?
  6. Do you feel like you were encouraged to be yourself as a child?
  7. Did you have a strict childhood?
  8. What do you remember most about Christmas as a child?
  9. What aspect of your personality has remained the same since you were a child?
  10. As a child, what did you want to be when you grew up?
  11. What’s your happiest memory from your childhood?
  12. What was your favorite toy?
  13. Did you used to enjoy school?
  14. Do you remember your first day at school?
  15. Do you still speak to any of your childhood friends?
  16. At what age did you stop believing in Santa?
  17. Did you have an imaginary friend?
  18. Do you think the childhood version of you would be proud of who you are today?
  19. What was your favorite Christmas gift?
  20. What was your worst childhood fear? Do you still have that fear?

Thinking about our childhoods can be a really fun experience. It may bring sad or happy emotions, depending on how our childhood was. It’s always a fun thing to talk about, especially when you are starting to get to know your conversation companion a little better.

This or That: Movie Edition

  1. Disney or Dreamworks movies?
  2. Classic Disney or Pixar?
  3. Action or comedy?
  4. Rom-com or horror?
  5. It’s a Wonderful Life or Elf?
  6. Hocus Pocus or The Nightmare Before Christmas?
  7. A scary movie for Halloween, or a classic Halloween comedy?
  8. Animated or live action?
  9. Harry Potter or Lord of the Rings movies?
  10. Star Wars or Indiana Jones movies?
  11. Home Alone 1 or Home Alone 2?
  12. Movies with or without subtitles?
  13. Watch a movie in the theatres or watch it from the comfort of your sofa at home?
  14. A predictable plot twist or a cliffhanger ending?
  15. Black and white movie or a 3D movie?
  16. A movie based on your favorite book or a movie based on your favorite singer?
  17. What would you rather watch: a movie with bad acting or a movie with bad CGI?
  18. Marvel movies or DC movies?
  19. Favorite Hollywood Jen: Jennifer Aniston and Jennifer Lopez?
  20. Favorite Hollywood Chris: Chris Hemsworth or Chris Pratt?

These interesting movie related questions will have your conversation companion desperate for a cozy movie night with you. These questions may even strike a fun debate between the two of you if you have a slightly different opinion!

Personal questions about the future

  1. Would you like to have children one day?
  2. How many children would you like to have?
  3. Would you like to get married?
  4. Where do you see yourself in 10 years?
  5. Do you have a ‘five-year plan’?
  6. Do you want to travel a lot in the future?
  7. Do you see yourself working at your current job for the long haul?
  8. Do you envision a happy future for yourself?
  9. Do you want to grow old ‘gracefully’ or would you consider cosmetic surgery?
  10. At what age would you like to retire?
  11. Do you see yourself moving to a different town, state, or country in the future?
  12. Is work the most important thing in your life?
  13. Do you want a large family or a small one?
  14. Do you wish you could see into your future?
  15. Do you plan to go back to college in the future?
  16. Do you plan to own your own business in the future or are you happier working for someone else?
  17. Do you want to own your own place?
  18. Would you rather live in the country, city, or suburbs?
  19. Would you homeschool your children or send them to an actual school?
  20. What do you most want to achieve by the time you are 80?

These questions are, of course, rather personal. For this reason, they probably shouldn’t be asked to just anyone, especially if you have only just met them. Save these fun questions for someone you have been on a few dates with as a way of getting to know them better and finding out if you have similar plans for the future.

Career Questions

  1. Do you like your current boss?
  2. What was the first job you ever had?
  3. Are you currently doing your dream job?
  4. How many jobs have you had?
  5. What was the worst job you ever had?
  6. Would you ever or have you ever worked for a family member?
  7. Would you hire a family member if you had your own company?
  8. What is the most time you have worked at a job? What was it?
  9. What is the least amount of time you worked at a job? What was it?
  10. Have you ever worked in retail or hospitality? Did you enjoy it?

For many people, their career is their whole life. It is what brings them meaning. For others, their job is merely just a necessity that allows them to live and get by. These questions are interesting to find out how your conversation companion or date views their career. It may even inspire them or you to strive for some new career goals.

This or That: Food Edition

  1. Chocolate or vanilla fudge?
  2. Dr. Pepper or Root Beer?
  3. Chinese takeout or a takeout pizza?
  4. Fries with ketchup or mayonnaise?
  5. Bagel or English muffin?
  6. Cupcake or cookie?
  7. Warm fudge brownie or freshly baked apple strudel?
  8. Roast chicken or roast beef?
  9. Egg nog or hot chocolate?
  10. Mulled wine or hot apple cider?
  11. Swedish fish or gummy worms?
  12. Cosmopolitan or Mai Tai?
  13. Cold pizza the next day or cold Chinese takeout the next day?
  14. Chips with salsa or guacamole?
  15. Fish sushi or vegetable sushi?
  16. McDonald’s or Burger King?
  17. Chocolate milkshake or strawberry milkshake?
  18. Dark chocolate or milk chocolate?
  19. Wendy’s or In-N-Out?
  20. Steak or lobster?

Some super difficult food decisions that will get your mind doing overtime and your mouth salivating. Hey, it may even lead to another date to one of the fast food restaurants mentioned!


  1. What are your pet peeves?
  2. Would you change anything about yourself? What is it, and why?
  3. What is the worst restaurant you have ever eaten at?
  4. Who was your most hated teacher at school? Why did you hate them so much?
  5. What celebrity can you just not stand the sight or sound of?
  6. Who is the worst singer in your opinion?
  7. What was the worst movie you ever saw at the theatres?
  8. Tell me about the coworker that annoys you most?
  9. What’s your biggest turn off in another person?
  10. What unpopular opinions do you have about things everyone else seems to love?

It can’t all be sunshine and rainbows all of the time! It’s only natural to feel like a Negative Nelly every now and then. Making time to talk about your dislikes with another person can actually be really cathartic. Plus it is actually thought that shared dislikes make for better friends and more binding between two people.

This or That: Music edition

  1. Country music or hip hop?
  2. Cardi B or Nicki Minaj?
  3. Rock music or pop music?
  4. N-Sync or Backstreet Boys?
  5. Beyonce or Lady Gaga?
  6. A huge stadium concert or an intimate gig in a small venue?
  7. A cheery pop song or an emotional ballad?
  8. Taylor Swift or Miley Cyrus?
  9. Queen or Aerosmith?
  10. Rap music or heavy metal?

As we have already mentioned, talking about music is bound to get even the shyest person engaged in a conversation. These quick and easy questions have simple answers to them and will hopefully lead on to a full-blown conversation.

Unpopular opinions

  1. Should ketchup be kept in the refrigerator?
  2. Is bacon really that good?
  3. Do you like Nickelback?
  4. Do texts need emojis?
  5. Is orange juice better with pulp?
  6. Is Nutella overrated?
  7. Is Halloween better than Christmas?
  8. Should chocolate be kept in the refrigerator or at room temperature?
  9. Is Apple really the best brand of phone?
  10. Is Friends a good comedy TV show? Was it better in the context of the 1990s and early 2000s or does it stand the test of time today?

Some very controversial questions lie above us. These could make or break the relationship you have with your conversation companion, but nonetheless, they are super fun to debate over!

‘Don’t think about it’ questions

Just a little note before we give you these questions…. These questions are designed to be answered without really thinking about it. You should answer with the first thing that comes into your head.

  1. If you could teleport anywhere in the world right now, where would you choose?
  2. Would you rather shrink to the size of an ant right now or grow to the size of an elephant?
  3. Quick – describe yourself in 3 words!
  4. If you were a dog, what breed would you be?
  5. Do you like tattoos?
  6. Did you shower this morning?
  7. How do you like your eggs in the morning?
  8. What’s your favorite day of the week?
  9. Have you ever punched someone?
  10. Mario or Luigi?

These questions need to be answered as quickly as possible. Think of it as a super-fast lightning round. Some of these questions are a little bit cheeky and personal, but they are sure to get a giggle and a smile. The randomness of some of the questions alone will make you seem like a comic genius, and you can playfully fake-‘judge’ them if they answer with anything shocking! A great round of questions for someone you have been flirty on a few dates with.

Top Three’s

  1. What are your top three video games?
  2. Name your top three Disney movies.
  3. What are the top three places you have visited?
  4. Who are your top three ‘most called’ contacts on your phone?
  5. What are your top three attributes you look for in a romantic partner?
  6. Name your top three rock bands.
  7. What are your top three home cooked meals?
  8. What novels have made their way into your top three?
  9. Where are the top three destinations you want to visit?
  10. What are your top three horror movies?
  11. Who are the top three people you can rely on?
  12. What are your top three ‘turn-ons’ in a romantic partner?
  13. What are the top three movies on your all time favorites list?
  14. What are your top three favorite songs by The Beatles?
  15. Which takeout restaurants are in your top three?
  16. What are your top three romantic gestures to do for a partner?
  17. Name your top three favorite toppings for ice cream sundaes.
  18. What are your three favorite things about the holiday season?
  19. Which three animals would you choose as your favorite?
  20. What are your top three sports to watch?

Sometimes picking just one favorite can be super difficult! Expand the choices a little and ask them their ‘top three’ of something. Remember to share yours too and see if you have any that are the same.

Final word

There you have it! We have supplied you with over 200 different questions you can add to your mental repertoire of fun and interesting things to talk about. Whether you are on a first date, making small talk at an event, or getting to know your besties a little better, you are sure to find some intriguing questions above.

Lots of the questions we have listed can be easily adapted to subject topics that suit you and the person you are talking to. This gives you infinite options of what to ask them. One thing is for sure, your conversations will never again be dry and boring. You will forever be known as the person who asks the most fascinating questions, and you will likely get a chance to share your answers with them, too. I mean, what better way to get to know someone, right?

Remember, depending on who you are talking to, some of the questions may not be suited to them. By this we mean, if you are just chatting to someone at a party that you have only just met, it may be wise to keep back some of the more cheeky and personal questions and instead choose some of our more general questions about food or music.

Likewise, if you are asking questions to a possible romantic partner after a few dates, don’t be afraid to shake it up and get a little more cheeky!

We hope you have enjoyed reading our article and have found some super Fun Questions to Ask.