100 Conversation Questions

  1. What is something you've never done but would like to try to do?
  2. What is something you've tried but would never do again?
  3. Are you a hoarder or saver?
  4. Are you usually early, late, or on time?
  5. What is your best skill/talent?

  1. What do you like least about living in your city/town?
  2. What do you like most about living in your city/town?
  3. Do you usually break the rules or follow them?
  4. Are you a leader or a follower?
  5. Do you wake up by yourself, to an alarm, music, or have someone else wake you up?
  6. Are you more of a spontaneous or structured person?
  7. How would your friends and family describe you?
  8. How have your goals changed as you've gotten older?
  9. Describe your dream house to me.
  10. What's the best thing to do on a hot summer day?
  11. What's the best thing to do on a cold winter day?
  12. What is your favorite smell?
  13. Do you prefer to receive money or an actual gift?
  14. What is your favorite day of the year?
  15. Are you messy or organized?
  16. Are you a heavy or a light sleeper?
  17. Do you smile for pictures?
  18. Do you wear slippers at home?
  19. Do you remember the last dream you had?
  20. How have you changed since you were a kid?
  21. Do you untie your sneakers before taking them off?

  1. What are three websites that you visit daily?
  2. What are three smart phone apps that you can't live without?
  3. How do you keep up to date with the news?
  4. What was the last picture you took on your phone?
  5. How often do you use your phone?
  6. What technology or business do you think will be obsolete within the next 10 years?

  1. What is your morning routine like?
  2. What is your evening routine like?
  3. What is the first thing that you think of in the morning?
  4. What is the last thing that you think of before you go to sleep?

  1. If you knew you couldn't fail, what would you do?
  2. If you could go back in time and change one thing, what would that be?
  3. If you could invent a holiday, what would it be?
  4. If there was an extra hour every day, what would you do with it?
  5. If you had to give up one of your five senses, which one would it be and why?
  6. What would you do if you won the lottery?
  7. If you became president, what is the first thing you would do?
  8. What would you do if you couldn't use the internet or watch TV for a month?
  9. If you could try out any job for one week, what job would you choose to try?
  10. If you were the opposite gender for one day, what would you do?
  11. If you could eliminate one thing that you did everyday, what would it be?
  12. If you could spend one hour with any living person, who would it be and what would you choose to do?

  1. Did you have any nicknames growing up?
  2. What is the worst injury you've had.
  3. What jobs have you worked at?

  1. What is the latest you stayed up until this past week?
  2. What is the earliest you woke up this past week?
  3. What are your favorite and least favorite parts of your week?
  4. What did you learn in this past week?

  1. What do you think your life will look like in 10 years?
  2. What would you like to do when you retire?
  3. What age do you want to live to?

  1. After a long day, do you prefer to hang out with friends or spend time alone?
  2. What is your favorite brand?
  3. What do you like to do to celebrate your birthday?
  4. What is your favorite thing to do on a rainy day?
  5. What do you like to spend your money on?
  6. Do you prefer to relax in your free time or do something active?
  7. Do you shower in the morning or at night? Why?
  8. What is your favorite party/board game?
  9. Do you prefer to wear fashionable clothes or comfortable clothes?

  1. What's your favorite comfort food?
  2. Do you prefer to eat at home or eat out?
  3. What food do you like to snack on?

  1. What is your favorite dessert?
  2. Do you prefer sweet or salty snacks?
  3. If someone you were trying to impress was coming over to your home for dinner, what would you make for them?
  4. What was your worst restaurant experience?
  5. What's your favorite non-alcoholic drink?
  6. How important is the decor of a restaurant to you?

  1. What type of movies do you like to watch?
  2. Would you rather watch or play sports?
  3. What do you use to listen to music?

  1. Do you prefer to travel or stay close to home?
  2. When going on a vacation, would you prefer to join a tour or plan out everything by yourself?
  3. What's your favorite thing about going on vacation?
  4. What's your least favorite thing about going on vacation?
  5. Have you ever gone on vacation by yourself?
  6. What do you like to do when you go to the beach?

  1. Do you prefer to have many friends or just a few close ones?
  2. Do you have a big family?
  3. What is the first thing that you notice about someone of the opposite gender?
  4. What do you look for in a girl/guy?
  5. What qualities do you value most in a friend?
  6. What is the first thing that you notice when meeting someone new?

  1. What do you think the best invention is?
  2. What is your favorite place to be?
  3. Tell me your best advice?
  4. Have you ever been to ConversationStarters.com? (shameless plug)
  5. If you could learn any skill, what would it be?
  6. What is the meaning of your name?
  7. Do you believe in luck or do you believe that people make their own luck?
  8. What is your favorite conversation starter?
  9. If money was not an issue, what would you do with your life?

Also see: Random Conversation Generator | How to Start a Conversation | Open Ended Questions

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