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01:59 Don't be afraid of vulnerability.
02:19 Do ease into more deeper and more difficult questions.
02:42 Do understand the context of your conversation.
03:09 Do give other people some time to warm up.
03:24 Don't beat the dead horse along the way.
03:58 Listen carefully to what people say.
04:28 Don't just have a cookbook of questions.
04:51 Do be prepared for unexpected answers.
04:57 Ask openended questions.
05:21 Never ask a question you wouldn't be comfortable to answer yourself.

Starter questions:
What do you do when you're not working?
Did you choose your profession or did it choose you?
What would you do if you won the lottery?
What is your favorite way to relax?
What is your favorite book to read?
What makes you laugh the most?
What is your favorite holiday?
What was the last book you read/movie you saw?
What are your favorite TV shows?
What is one thing you're glad you tried but would never do again?
When people come to you for help, what do they usually want help with?
Who’s your go to band or artist when you can’t decide on something to listen to?
What’s something you like to do the oldfashioned way?
What is something you have only recently formed an opinion about?
What are you interested in that most people haven’t heard of?
What is something you think everyone should do at least once in their lives?
What is something that people are obsessed with but you just don’t get the point of?
Where is the most interesting place you’ve been?
What is the luckiest thing that has happened to you?
What is your biggest pet peeve with modern technology?
What object have you been searching for with no luck?
What social customs do you wish would just disappear?
What quirky things do people do where you are from?
Who or where would you haunt if you were a ghost?

Now, once you're past starter questions, you want to dig a little deeper and really understand what the other person is all about. So, once you've gone through these introduction questions that are fun, you move on to some more indepth questions.

What gets you out of bed every day?
What do you value in a friendship?
What do you say more often in life: yes or no?
What is on your bucket list?
What would you tell your teenage self if you could go back in time?
What is the hardest part about raising children?
What do you wish was different about modern parenting?
What gets you fired up?
What mistake do you keep making again and again?
What have you created that you are most proud of?
What’s the best thing you got from your parents?
What’s one responsibility you really wish you didn’t have?
What’s the best and worst thing about getting older?
What chance encounter changed your life forever?
What do you regret not doing?
Do you believe in second chances?
Do you want to retire to live or live to retire? 
What are some things you wish you could unlearn?
What do you wish your brain was better at doing?
What or who couldn't you live without?
When do you feel the most confident?
If a crystal ball could tell you anything about your future, what would you want to know?
If you could change one personal decision in your past, what would that be?
What goal are you working on now?
What scares you about the future?
When was the last time you cried?
Do you believe people are at the whim of destiny or that they can create it themselves?
Who is someone that you miss having in your life?
What question do you always want to ask people but don't have the courage to ask?

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