151 This or That Questions to Start a Fun Conversation

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What is your favorite way of starting a fun conversation?

Maybe you aren’t as good as starting good conversations. It is also possible that you might have found yourself in a situation where you find it challenging to start a conversation. 

You should know that conversations play a significant role in allowing us to know other people better. One of the best you can begin a fun conversation is by stopping the idea of trying to be exciting and instead be interested in the other person. 

In this case, I am going to offer 151 this or that questions, so that you don’t leave the other person burdened with the idea of struggling to lead or continue talking.

I have tried to group the questions in various categories to easily find out the questions that fit your particular scenario.  Some will help you make new friends. And other questions can help you spark a meaningful conversation with your old friends, young children, and partner if you are married.

This or That Questions for Couples

When you have been with someone for a long time, it can be interesting in finding out something new about your partner. But you shouldn’t worry.

Regardless of how long you have been married, you can still discover something new about your partner. To have a better and funny conversation with your partner, you must follow the tips highlighted below.

  1. Would you hold our hands in public or put your arm around my shoulder in public?
  2. Would you hang out with your friends or stay alone with me on the weekend?
  3. Would you make me sad by winning an argument since you are right or lose an argument to make me happy?
  4. Would you keep me waiting or rather wait for me to attend your favorite event?
  5. Would you have a poor partner who is witty or a partner with lots of money but doesn’t have a sense of humor?
  6. Should you declare in public that you love me or convey that you love me in private?
  7. Would you spend your special occasions with the entire family or with just me?
  8. Would you enjoy the present with me and stay young or experience the future but grow old?
  9. Would you give up fast food or parties?
  10. Would you travel on a plane with frogs or bus with a snake?
  11. Would you rather have one of your hands bigger or one of your ears bigger?
  12. Would you rather live in a small clean house or in a dirty and messy bungalow?
  13. Would you rather be embarrassed in front of your in-laws or front of your parents?
  14. Would you rather be hated for being good or be talked about being bad?
  15. Would you rather be locked at home during winters or travel to a desert during summers?
  16. Would you rather forget your mobile phone without a security lock at your parent’s house or forget your collection of favorite movies?
  17. Would you rather fake your death by sleeping for one year or go to jail?
  18. Would you prefer to work hard at a well-paying job or work less at a low paying job?
  19. Would you rather have a private wedding or a wedding in a public venue where strangers can watch?
  20. Do you prefer staying up late or getting up early?
  21. Would you rather have an ambitious partner or a hilarious partner?
  22. Would you rather be someone who is loved or feared by all people?
  23. Would you rather report the wrongdoings of your partner with your family or friends?
  24. Would you rather go for a photo booth or take random selfies with your partner?
  25. Would you rather have a clean partner and freak or a partner who is dirty and lazy?
  26. Would you be with a person who is obsessed with an old fashion or someone who does not know anything about fashion?
  27. Would you rather wake up late and spend your day alone or wake early and spend your time with your partner?
  28. Would you rather prefer to stay together with your partner or stay away and meet a few times a month?
  29. Would you rather date a shy guy or confident guy?
  30. Would you rather live in a deep forest with complete privacy or live in a busy neighborhood with excellent views?
  31. Would you like to be in a relationship with someone who never hugs you or someone who never argues?
This That Questions for Couples | funny this or that questions adults | deep this or that questions
  1. Would you rather have a briefcase with $10 million or find true love but live in poverty?
  2. Do you prefer having a few friends or hanging out with many acquaintances?
  3. Do you prefer an outdoor or indoor date?
  4. Would you prefer to stay for one month without taking a shower or stay for one month without internet access?
  5. Out of all the dates that we have ever gone, which one do you think was your favorite?
  6. Would you engage in a conflict or avoid it?
  7. Would you prefer us to buy luxuries and live in a rented house or live our own house without access to luxuries?
  8. Would you rather live in a fantastic city with a boring job or a boring city with a good job?
  9. Would you rather be brilliant and ugly or dumb and good looking?
  10. If you were allowed to change your career, which one could you choose, and why?
  11. Would you prefer us to take our children to a day school or a boarding school, and why?
  12. Would you prefer to work in the same company with your partner or rather be jobless?
  13. Would you prefer me to assist you to calm down when you are upset or leave you to calm down by yourself?
  14. Would you rather call or text me when you need something urgently?
  15. Would you rather have all the love that you desire or have all the money that you desire?
  16. Would you rather live and cause the death of a child or sacrifice yourself and save the life of your child?
  17. Would you rather cook meals for yourself or cook together with me?
  18. Would you rather eat your favorite food by yourself or eat your worst foods with me?

Whether you're striving to achieve personal or professional goals, having an accountability partner can make all the difference. If you want to learn more, then check out this video:

This or That Questions for Children

Children are particularly fragile when it comes to conversations. One of the best ways you can encourage kids to open up about their lives is by having a habit of starting a daily fun conversation that makes them feel connected to you.

(And if you want an additional resource, here are more conversation starters for kids.)  

  1. Would you play outside or play video games?
  2. Would you rather lie to your best friend or lie to your parents?
  3. Would you rather do school work by yourself or as a group?
  4. Would you prefer your room to be painted in one color or be painted in different colors?
  5. Would you rather sing or dance?
  6. Would you rather be on a TV show or meet your favorite celebrity?
  7. Would you rather spend a whole day in a large museum or spend an entire day in a huge garden?
  8. Would you rather drink orange juice or drink tea during breakfast?
  9. Do you prefer having five more sisters or brothers?
  10. Would you prefer small feet or small hands?
  11. If you were to get a face painting, would you prefer your entire face to be painted or just a small section? Why?
  12. When you make a mistake, would you prefer lying or telling your parents the truth?
  13. Would you rather have ice cream or chocolate?
  14. Would you prefer us to visit your grandmother or aunt this weekend?
  15. What favorite foods do you prefer? Why do you like them?
  16. Would you rather have bad gifts for your birthday or no gift at all?
  17. Would you rather play dodgeball or hide and seek?
  18. Would you rather see a tiny giraffe or a giant ant?
  19. Would you rather be a dog or a cat?
  20. Would you rather be a vegetarian or only eat meat?
  21. Would you rather be taller or smaller?
  22. Would you rather share your birthday cake with your friends or with your parents?
This or That Questions for Children | this or that questions to ask a girl | deep this or that questions

This or That Questions for Teens

It can be challenging to talk with teens. However, if you get an opportunity to speak with teens, you should follow the following tips to encourage them to open up about their issues. 

The key here is to listen to their emotions and to avoid trying to solve their problems.  Here are a variety of this or that questions that you can ask:

  1. Would you rather be the worst player on a winning team or be the best player on a losing team?
  2. Would you prefer having friends who are better looking than you or friends who are smarter than you?
  3. Would you prefer to download electronic books or go to the library? Why?
  4. Would you rather have a private teacher at home or have an extra lesson at school?
  5. Would you prefer to take the public bus to school or rather be driven by your dad to school?
  6. Would you prefer to spend your weekend outdoors or indoors?
  7. Would you prefer to be popular in real life or be popular only on social media?
  8. Would you prefer wearing clothing or leather clothing?
  9. Would you rather eat only fruits for one month or only eat vegetables for one month?
  10. Would you rather meet your celebrity crush or your mentor?
  11. Would you rather have your best friend who an extrovert or one who an introvert?
  12. Would you prefer having a female best friend or a male best friend?
  13. Are you closer to your dad or mom?
  14. Would you rather fall sick and fail to sit for a test or fail a test that read hard for?
  15. Would you rather miss a party that your best friend in school invited you to or sneak out of the school and get punishment from your parents?
  16. Would you rather assist your best friend in passing an exam or assisting your crush in passing an exam?
  17. Would you rather move into an attic or share your room with your siblings?
  18. Would you prefer to wear casual outfits to school or wear a uniform to school?
  19. Would you prefer to be in a relationship with someone in your class or be in a relationship with someone who is far away?
  20. Would you rather win cash or win a gift card?
  21. Would you rather have a teacher who funny but poor in teaching or have a teacher who effective at teaching but very mean?
  22. Would you prefer to be the smartest student in school or be the best footballer in school?
  23. Would you prefer to have your classmates like you, but your teachers hate you or have your teachers like you, but your classmates hate you?
  24. Would you prefer to be the only child or have many siblings?
  25. Would you rather be the youngest child or the oldest child?
  26. What are you rather engage in your hobbies or never engage but receive $5 million?
  27. What are your future plans? Would you take a break after high school or start working or proceed to college?
This That Questions for Teens | this or that questions for adults | this or that questions for sisters
  1. Do you prefer spending your free time with your family or friends?
  2. Do you like watching TV or read books during your free time?
  3. If you could get a chance to travel to any place of your choice in the world, would you travel abroad or stay in your own country.
  4. Would you prefer to make less money and have more free time or make a lot of money but have less free time?
  5. Would you wish you were younger or older? Why?
  6. Would you like to stay indoors or outdoors?
  7. Would you rather be a good person who lives a simple life or is a bad person but innovates something that becomes a success?
  8. If you are given two options of either becoming a great motivational speaker or an athlete, which one would you prefer?
  9. Would you rather watch an incredible movie or read a book with a fantastic story?
  10. Would you rather be a doctor or a pilot?
  11. Would you rather forget the birthday of your best friend or your best friend to forget your birthday?

Fore more questions, check out our post on would you rather questions for teens.

This or That Questions for Adults

  1. Would you rather lose your sense of smell or your sense of taste?
  2. Would you rather work for someone you love, but make little money or work for someone you hate but make a lot of money?
  3. Would you rather marry a bright person in this world or marry the hottest person in this world?
  4. Would you rather marry someone who doesn’t love you or someone who you don’t love?
  5. Would you rather have a phone with a weak signal or have one with slow internet?
  6. Would you rather frame your best friend for a crime you committed or be framed for a crime you didn’t commit?
  7. If you are arrested today without any explanation, whom do you think between your family or friends would defend you?
  8. Do you prefer to be famous or rich?
  9. Would you prefer to be the smartest person who lives or the funniest person alive?
  10. Would you prefer to live without a phone or live without a phone?
  11. Do you prefer shopping in-store or online shopping?
  12. Would you rather watch a movie in a packed theatre or sit down and watch a movie on your couch?
  13. Would you rather visit a museum or breach?
  14. Would you rather walk in the dark or drive in the dark?
  15. Do you love watching tattoos or movies? (If they have tattoos, they will tell why they are relevant to them and probably reveal a story behind them. On the other hand, if they don’t have, they can tell you what they think about them.)
  16. What kind of phone between android and iOS do you prefer?
  17. Would rather live on a farm with many plants and animals or live in a mansion in a city?
  18. Do you call or text more, and why? (Here's a list of conversation starters for texting so you can get to know each other better.)
  19. What sports do you hate or like playing?
  20. Do you like traveling in a group or alone?
  21. Which of your family members or friends do you most look up to? You can get to learn everything about the family
  22. What kind of conversation issues between political, religious, and social do you like, and why?
  23. Would you rather have earned a lot of money working in another company or get a loan and start your own business?
  24. Would you prefer staying single for the rest of your life or be forced into a marriage arranged by your parents?
  25. Would you prefer to be rich and depressed or poor and happy?
  26. Would you prefer someone to owe you a lot of money or you to owe someone a lot of money?
  27. Would you rather be middle class for the rest of your life or be homeless for ten years and after that become rich for your entire life?
  28. Would you rather look strong but, in a real sense, be weak or look weak but be strong?
  29. Would you rather be in a suit all day or be in your pajamas all day?
  30. Would you rather eat the same food daily or different food each day?
  31. Would you rather lose your luggage or have your flight to your favorite destination delayed for one day?
  32. Would you rather be happy and ignorant or knowledgeable and sad?
  33. Would you rather be stuck on a roller coaster or stuck in an elevator?
This That Questions for Adults | this or that questions to ask a guy | this or that questions for couples
  1. Would you rather be a moron is a world of geniuses or be a genius in a world of morons?
  2. Would you rather be stuck in s house alone or be held in the house with someone you hate?
  3. Would you rather be dumped by someone or dump someone else?
  4. Would you rather have your naked photo shared to all people that know you or run naked in the entire street?
  5. Would you rather go back to college or high school for one year?
  6. Would you rather live in a place which is always hot or always cold?
  7. Would you rather have a guide to assist you in exploring a new place or exploring on your own?
  8. Would you rather have your children embarrass you in public, or you embarrass your children the public?
  9. Do you prefer a small intimate gathering or a big blowout?

Final Thoughts on This or That Questions 

Asking fun questions can lead you to an exciting conversation. However, coming up with a fun question can be challenging. The good thing is that if you follow the above guide, you will find it easy to ask funny questions to any age group you are interacting with.

Now, if you’d like to discover even more conversational questions, then here are a few additional resources you can check out:

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.

this or that questions to ask a guy | this or that questions to ask a girl | this or that questions hard