100 Conversation Questions

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

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

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

  • What is your morning routine like?
  • What is your evening routine like?
  • What is the first thing that you think of in the morning?
  • What is the last thing that you think of before you go to sleep?

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

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

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

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

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

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

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

  • What type of movies do you like to watch?
  • Would you rather watch or play sports?
  • What do you use to listen to music?

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

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

  • What do you think the best invention is?
  • What is your favorite place to be?
  • Tell me your best advice?
  • Have you ever been to ConversationStarters.com? (shameless plug)
  • If you could learn any skill, what would it be?
  • What is the meaning of your name?
  • Do you believe in luck or do you believe that people make their own luck?
  • What is your favorite conversation starter?
  • 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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