220 Questions in 22 Parts

220 Questions Part 1 of 22

1. What’s something you wish you could do again for the first time? 

2. Name a hard but important lesson you’ve learned.

3. What is hard for you but easy for others? 

4. What do you want but will never have? 

5. What’s your most controversial opinion? 

6. What fictional character do you most relate to?

7. When do you feel like the best version of yourself? 

8. What book, movie or video game made you change the way you look at the world? 

9. What occupation do you admire but could never do?

10. Who is your nemesis? Why?

220 Questions Part 2 of 22

1. How are things getting better? 

2. How are things getting worse? 

3. What person do you most look up to? Why?

4. What story have you told people the most? 

5. What are your top 5 TV series?

6. What job would you choose to have if money were no object?

7. What’s the fastest way to make you mad? 

8. What is the most useless skill you have? 

9. What is your least favorite word? 

10. What have you learned this week that you’ll never forget? 

220 Questions Part 3 of 22

1. What’s the best way to spend a birthday? 

2. What one sentence about how to live sticks with you most? 

3. What’s a key memory that has an impact on your personality? 

4. What big mistake turned out just fine? 

5. What’s the biggest fight you’ve been in? What started it? 

6. What’s the dumbest thing you’ve bought? 

7. What do you know isn’t real, but want badly for it to exist?

8. Am you the Walrus?

9. What is something that gets weirder the more you think about it?

10. What would you title your autobiography?

220 Questions Part 4 of 22

1. How would you summarize your life so far in one sentence?

2. Who is the best person you’ve ever met? What made them the best? 

3. What’s something you predicted would happen and then actually did? 

4. What question would you really like answered? 

5. What is wrong with society? 

6. What was the hardest decision you’ve ever made?

7. You have one year to live. How do you spend it?

8. What is your favorite word? 

9. Have you ever cried in public? Why? 

10. What’s something you are terrible at? Will you improve one day? 

220 Questions Part 5 of 22

1. What always makes you smile? 

2. What do you value much more now that it’s gone? 

3. What expensive thing is definitely worth it? 

4. Who do you wish were still alive? 

5. What’s something you really wanted that turned out to be overrated?

6. If you could instantly quadruple your sense of smell, would you?

7. What’s the best gift you’ve ever been given? 

8. What have you created that you’re proud of? 

9. How are you different from your parents? 

10. What do you love that most people don’t? 

220 Questions Part 6 of 22

1. What do you hate that most people don’t? 

2. What’s one thing you really hate but have no good reason to?

3. What is your favorite thing? 

4. What’s the craziest thing you’ve done? 

5. What celebrity do you most admire? 

6. What small, insignificant thing gives you joy?

7. What’s a weird thing you do that nobody notices? 

8. What was the best day of your life?

9. Do you fit a stereotype? 

10. What can you forgive but never forget?

220 Questions Part 7 of 22

1. Two hours into a fun party, are you more energized or exhausted? Why? 

2. What is the best compliment you’ve ever received? 

3. What character trait makes you instantly respect somebody? 

4. What is a funny thing you’ve seen recently on the Internet? 

5. What’s your most vivid nightmare? 

6. Describe the first thing that pops in your mind when asked to describe the best day of your life.

7. Do you like this tag

8. What is easy for you but hard for others? 

9. What is your favorite quote? 

10. What is the most important quality you look for in a friend?

220 Questions Part 8 of 22

1. What scientific or technological advance blows your mind?

2. Is it better to be a grownup or a kid? 

3. What’s something that you wish was socially acceptable? 

4. Name the worst film you’ve ever seen. 

5. What would be the most alarming thing God could tell everyone?

6. What was an opportunity you turned down? Why? 

7. Where would you live on the planet if money didn’t matter? 

8. What immediately makes you think less of somebody?

9. What is an annoying phrase or word that should just stop? 

10. What do people assume because of your appearance? Are they right or wrong? 

220 Questions Part 9 of 22

1. How would you like to die? When? 

2. What were the longest 5 minutes of your life? 

3. What did you love doing, but would never do again? 

4. What object best defines your identity? 

5. Do you believe in fate? Or is everything mostly chaos?

6. Do you wish you were more involved with your extended family? Why or why not?

7. What is always funny? 

8. Can you still recite the longest thing you’ve memorized? 

9. What’s changed the most about you in the past two years? 

10. What’s your greatest accomplishment?

220 Questions Part 10 of 22

1. What fear do you have that is completely justifiable? 

2. Who was the last person you talked to? 

3. What, if anything, is too serious to be joked about?

4. Are you currently chasing what makes you happy? Why or why not?

5. What was the worst day of your life? 

6. What are you proud of that you haven’t done? 

7. If you could give a thank you note to anyone in the world, who would it be? Why? 

8. Describe your perfect meal.

9. What is something you never thought you’d be able to do, until you actually did it?

10. If you could fix one major world problem, what would you pick?

220 Questions Part 11 of 22

1. What will you likely forget someday but never forgive? 

2. What question do you love answering? 

3. What grudge do you need to let go of? 

4. What was the best opportunity you ever received? How did it work out?

5. What’s the biggest difference between this generation of kids and older people? 

6. What is the quality you admire the most in the person you like the least? 

7. What are the books/movies/games/things that always make you feel better when you get down?

8. What’s the last really generous or kind thing you did? 

9. What’s a misconception people have about people your age? 

10. If you could change one thing about yourself physically, what would you change?

220 Questions Part 12 of 22

1. What would you like your lift to be?

2. What are you either at rock bottom or peaking on? 

3. What’s a trend you can’t stand? 

4. What did you expect to hate but actually loved? 

5. What core principles do you have that won’t change? 

6. Has anyone close to you ever died? What helped you get through it?

7. If you could inhabit another person for a day and just watch, who would you pick? 

8. What’s something you wish you enjoyed but never can seem to?

9. What is the worst thing about the place you live? What is the best thing?

10. What historical event would you most like to have experienced?

220 Questions Part 13 of 22

1. Have you gone through any phases in your life? What is the most notable one?

2. How are you feeling today? 

3. What happened the last time you were punished? Was it fair? 

4. What’s your favorite song lyric? 

5. What was the scariest moment of your life so far?

6. What are your top 5 TV miniseries? 

7. What do you get the most compliments about?

8. What smells bring back memories? Why? 

9. What’s the worst piece of advice you’ve been given? Did you follow it? 

10. What do you wish you could remember better? 

220 Questions Part 14 of 22

1. What is worth dying for? 

2. Would you rather fight a horse-sized duck or 100 duck sized horses?

3. How often do you feel you let people down? 

4. If you could ask your future self one thing, what would it be?

5. What 3 things would you like to accomplish before dying? 

6. When was the last time you really, really laughed? Why? 

7. If you had a billboard that everyone on the planet had to read, what would it say? 

8. What’s an obscure fact you know?

9. What film, video game or book has the best ending? 

10. What are you really tired of explaining? 

220 Questions Part 15 of 22

1. Name something you’re irrationally afraid of.

2. If you could change one thing about your family, what would it be? 

3. In a fight to the death what’s your go-to strategy? 

4. What makes you feel at peace? 

5. If you can’t sleep, what do you usually think about?

6. What about yourself took the longest to accept? 

7. What’s your favorite conspiracy theory? 

8. What’s the first thing you’d like people to notice about you? 

9. What situation made you feel like an idiot?

10. What’s something you’re secretly proud of? 

220 Questions Part 16 of 22

1. If you could use a time machine, would you rather have one that only goes back in time or only goes forward?

2. Do you think humanity will go extinct? If so, when? 

3. What single event or decision most affected the rest of your life? 

4. What was the worst year of your life? The best?

5. What would you like to be remembered for?

6. What has been the biggest change of heart you’ve had? Why?

7. Do you need some advice? 

8. Somebody is going to borrow your life for the day. What’s your advice to them? 

9. What outfit makes you feel invincible? 

10. What worries you a lot? What would fix it? 

220 Questions Part 17 of 22

1. What is something you’re terrible at but wish you could do well?

2. What is the most trivial thing about which you have a strong opinion?

3. Have you ever eaten bugs on purpose?

4. Which superpower would you prefer: the ability to fly or invisibility? 

5. Where do you wish you had grown up?

6. What do you want to tell someone but haven’t yet? Why not? 

7. What’s your favorite family tradition? 

8. What’s a habit you’d like to build?

9. Is it smart to be a pessimist?

10. What’s a habit you’d like to break?

220 Questions Part 18 of 22

1. What have you improvised really well?

2. Can people really change?

3. What are the best & worst things about the two people you spend the most time around outside of family?

4. What’s something you like about someone listening that you’ve never told them?

5. Can being alone become a habit?

6. What’s a grooming, beauty or fashion tip that people should know?

7. What’s an insult you’ll always remember?

8. When was the last time you cringed? Why?

9. What’s a terrible example of doing what the majority says?

10. What’s the worst TV show ever?

220 Questions Part 19 of 22

1. What’s a terrible example of going it alone?

2. Who is the worst villain ever?

3. What are you planning on doing but probably won’t?

4. What animal would you be for a day?

5. What’s the most overrated film you’ve seen?

6. What one thing could you do to make the people around you happier? 

7. Who do you think is a really good leader? What makes that person so?

8. Would you prefer the superpower of zoom vision or zoom hearing at will? 

9. Would you rather be a funny idiot, or a humorless genius?

10. What are your top 5 favorite films? 

220 Questions Part 20 of 22

1. What used to scare you?

2. What makes someone funny? Who is a good example of this? 

3. Has anything supernatural or spooky ever happened to you? 

4. When was the last time you put in an extreme amount of effort? 

5. What is the most beautiful thing in the world? 

6. What will you be nostalgic for in 30 years?

7. What 3 things are most essential in life?

8. Have you ever experienced culture shock?

9. If you and one other person were to get matching tattoos, what would the image be? Who is the other person? 

10. Did you slap anyone lately? Did you want to?

220 Questions Part 21 of 22

1. Any intrusive thoughts you want to talk about?

2. Would you and your clone get along? 

3. What’s the worst color? Where did you last see it? 

4. What would you change if you knew you were never going to die?

5. What’s something on your to-do list that somebody else listening could do? 

6. What would you buy if you won $1 million? $1 billion? 

7. If AI took all the jobs, what would you do? 

8. What’s a famous superpower you’d never want? 

9. What’s something you like about somebody who is listening? 

10. If you could have an extra door in your house that opened to anywhere, where would you choose for it to lead?

220 Questions Part 22 of 22

1. How badly can you hum a song that we can still guess what it is? 

2. What do people complain about but we’re actually pretty lucky to have? 

3. Who do you know that gets teased too much? Why? 

4. What makes a good parent? Could you be one?

5. What’s the most frequent thought you’ve had this week? 

6. What should be your New Year’s resolution next year? 

7. What do people of the opposite gender not understand about your gender? 

8. Have you ever been to a different country?

9. Have you ever gotten sick in public?

10. Recall a funny moment on a family vacation.