What are you most grateful for, right now, in this moment?

Where & when do you get your best ideas?

What’s your most urgent priority for the rest of the year?
What’s your guiltiest of guilty pleasures?
What’s the worst piece of advice you’ve ever been given?
What’s the best compliment you’ve ever received?

What’s the hardest thing you ever had to write — and why?

Have you ever dreamed about starting a business? (Or if you’ve already got one — a new
business?)

Do you believe that people deserve to be happy?

Are you living your life purpose — or still searching?

Are you useful in a crisis?

How long have you known ______ ?

What is your hobby?

Do you have kids? How many? How old are they?

Do you think everyone has the capacity to be a leader?

Has a teacher ever changed your life? How so?

Casual questions to get to know someone
If you didn’t have to sleep, what would you do with the extra time?

What’s your favorite piece of clothing you own / owned?

What hobby would you get into if time and money weren’t an issue?

What would your perfect room look like?

How often do you play sports?

What fictional place would you most like to go?

What job would you be terrible at?

When was the last time you climbed a tree?

If you could turn any activity into an Olympic sport, what would you have a good
chance at winning medal for?

What is the most annoying habit that other people have?

What job do you think you’d be really good at?

What skill would you like to master?

What would be the most amazing adventure to go on?

If you had unlimited funds to build a house that you would live in for the rest of
your life, what would the finished house be like?

What’s your favorite drink?

What state or country do you never want to go back to?

What songs have you completely memorized?

What game or movie universe would you most like to live in?

What do you consider to be your best find?

Are you usually early or late?

What pets did you have while you were growing up?

When people come to you for help, what do they usually want help with?

What takes up too much of your time?

What do you wish you knew more about?

Somewhat personal questions to get to know someone

What question can you ask to find out the most about a person?

When was the last time you changed your opinion / belief about something
major?

What was the best compliment you’ve received?

As the only human left on Earth, what would you do?

Who inspires you to be better?

What do you want your epitaph to be?

What did you think you would grow out of but haven’t?

In what situation or place would you feel the most out of place in?
What’s the dumbest thing you’ve done that actually turned out pretty well?

They say that everyone has a book in them. What would your book be about?

What is something you will NEVER do again?

What do you spend the most time thinking about?

What are some of the events in your life that made you who you are?

What do you wish your brain was better at doing?

There are two types of people in this world. What are the two types?

What is the strangest thing you have come across?

What is something you are certain you’ll never experience?

What dumb accomplishment are you most proud of?

If you could make one rule that everyone had to follow, what rule would you
make?

What are you addicted to?

What stereotype do you completely live up to?

What is something you can never seem to finish?

As you get older, what are you becoming more and more afraid of?

What is one of your favorite smells?

What would be the scariest monster you could imagine?

What song or artist do you like but rarely admit to liking?

What would you do if you knew you were going to die in one hour?

What book impacted you the most?

If you had to change your name, what would you change it to?

If life is a game, like some people say, what are some of the rules?

Who is / was your most interesting friend?

Have you ever given to any charities?

What is something that your friends would consider “so you”?

What risks are worth taking?

What can you not get right, no matter how many times you try?

If you could convince everyone in the world to do one thing at one point in time,
what would that thing be?

What do you take for granted?

What would be some of the most annoying things about having yourself as a
roommate?

What’s something you are self-conscious about?

What personality trait do you value most and which do you dislike the most?

What small gesture from a stranger made a big impact on you?

What gets you fired up?