Never have I ever Play Now

Conversation starters and ice-breakers are better used for newly-met people. Meanwhile, questions you ask your best friend goes a little further from “how are you’s” and “have you seen the latest viral thing?”

To inspire your conservations, here is a list of questions ranging from topics about their past to their future goals, fears and favorite things, as well as everything in between.

Questions about Their Past

People are molded by the experiences they went through. One way to understand a person’s beliefs, actions and goals is to learn about their past.

Don’t push if they’re not ready to answer some of your questions. There’s a reason people “move on” from their pasts. But if your friend opens up to any of the following questions, then prepare to meet your friend at a deeper level.

  1. What is your fondest summer vacation memory?
  2. Did you have any traumatic experiences as a child?
  3. What is your earliest memory ever?
  4. Did you ever have a mistake you wanted to handle differently if you can?
  5. What non-family relationship had the most impact on your growing-up years?
  6. Do you have a prominent scar? Where, when and how did you get it?
  7. Who was the last person who broke your heart?
  8. What is the craziest thing you’ve ever done?
  9. Do you have an embarrassing childhood memory?
  10. Which family tradition did you hate growing up, but was forced to do?
  11. Have you ever been arrested for anything?
  12. What band/artist helped you get through a rough patch in your life? Do you still like their music now?
  13. What is your favorite cartoon character growing up?
  14. Do you have a talent when you were a child that you no longer use?
  15. What was your drunkest memory?
  16. If you can make a do-over in just one part of your life, what would it be?
  17. Did you experiment with recreational drugs in the past?
  18. If you could go back and tell your childhood self something, what would it be?
  19. What year was your happiest? Why?
  20. What year was your saddest? Why?

Pop Culture Questions

Even something as trivial as finding out a friend’s secret-favorite reality TV show can be huge, if you discovered that you have the same likes/dislikes. Pop culture questions are light, silly and can definitely break the ice.

  1. Star Trek vs. Star Wars?
  2. Do you believe that aliens exist?
  3. Who was your first celebrity crush?
  4. Do you believe in ghosts?
  5. If you can be best friends with someone popular, who would it be?
  6. Do you have a favorite movie or TV show that you absolutely love, but is embarrassed to let anyone know?
  7. If you could go back in time, which historical person would you like to talk to?
  8. What TV show have you binged-watched more than 3 times already?
  9. Who is your favorite fictional character? Why?
  10. If you can be a pro athlete, what sport would you choose?
  11. Which movie is your go-to when you’re feeling sad?
  12. f you could learn any language or skill Matrix-style, what would it be?
  13. Do you love watching trailers before a movie screening? Or do you prefer to skip it altogether?
  14. Is there a movie so hyped by everyone, but you secretly hated?
  15. What kind of superpower would you like to have?
  16. Do you watch any reality TV that you hoped you didn’t?
  17. Is there a movie quote you live by?
  18. What childhood toy did you wish you kept for your future kids?
  19. If your life was turned into a biopic, which actor would you like to play yourself?
  20. Choose one band or music genre as OST for your biopic.

Deep Questions

These questions are probably best asked when you and your best friend are all alone.

  1. What do you think will happen to you after you die?
  2. Do you want kids? If yes, how many?
  3. Where do you hope to be 5, 10, 20 years from now?
  4. If you could move anywhere in the world, where would it be? And why?
  5. What more important to you now: career or personal life?
  6. Do you believe in destiny?
  7. How do you define freedom?
  8. If you were told you had only a year to live, how would you spend it?
  9. Would you donate an organ to someone you love?
  10. What is your biggest regret?
  11. What behaviors of another person are total turn-offs?
  12. If money was no problem, what job would you prefer doing?
  13. Have you met the one? If not, when will you know you’ve met the one?
  14. What is your least favorite thing about your house?
  15. Do you ever wish you had different parents or siblings?
  16. Who do you aspire to be?
  17. If you were to die today, what last song would you like to be playing?
  18. Are you afraid of dying?
  19. If you could change anything about your life now, what would it be?
  20. What is your weirdest fantasy?

Favorites and Fears

Questions about pet peeves, fears and favorite things really showcase how alike you are with your best friend…

  1. What is your biggest fear?
  2. Are you afraid to grow older?
  3. What is your favorite guilty pleasure food?
  4. What is the best gift you have ever received?
  5. Do you have a favorite summer destination? If so, where?
  6. What is the single-most thing you’re afraid of about your future?
  7. Do you prefer rainy, sunny or snowy days?
  8. If you are allowed to eat a dessert daily, what would it be?
  9. What’s your go-to, pick-me-upper ice cream flavor and brand?
  10. Which restaurant is your favorite?
  11. Do you have a favorite book of all time?
  12. Are you a dog person or cat person?
  13. What type of music do you love?
  14. Do you prefer eating out or dining in?
  15. Mexican food or Chinese food?
  16. If you can only eat just one salty snack for the rest of your life, what would it be?
  17. What are your favorite things to do during the weekend?
  18. If you can choose between living up to 100, or picking a date when to die, what would you choose?
  19. What vegetable do you avoid at all costs?
  20. What are your top 3 pet peeves?

Totally Random Questions

These questions can be a curveball, but they’re still awesome conversation-starters for you and your friends.

  1. If you win 50 million dollars from the lottery, what’s the first you’re going to do?
  2. Do you believe that the earth’s survival is being threatened?
  3. What’s the first thing you do in the morning?
  4. Do you like pineapple with burgers or pizza topping?
  5. Have you ever received a gift you totally hated? What was it?
  6. Would you say YES to bungee jumping or other extreme sports?
  7. If you were a musical instrument, what would you be?
  8. What would you wish for, if you were given 3 wishes?
  9. Do you remember your dreams in the morning?
  10. If you were an animal, what would you be?
  11. What is the most important value or attitude that a boyfriend/girlfriend must have?
  12. If you could trade lives with someone, who would it be?
  13. Do you think you’d survive being stranded on a desert island?
  14. How does your dream retirement look like?
  15. If you had to eat the same breakfast daily, what would it be?
  16. You receive 50 million dollars to start a business. What would it be?
  17. If you were given a chance to change your name, what would it be?
  18. Have you ever shoplifted?
  19. Spend unlimited money for a dream wedding, or travel the world?
  20. If you were given $100 to spend on just 1 store, where would you go?

✍️  August 29, 2020

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