Deep questions to ask friends

 If you had a whole day where you could do anything

you wanted, what would you do?
 What are you most proud of about yourself?
 What is your greatest accomplishment?
 What are you still hoping to accomplish?
 What do you want people to know about you?
 What do you need more of in your life?
 What do you need less of in your life?
 What do you feel has been your greatest “win” so far in
your life?
 What three words describe what you’re most grateful
for?
 Would you rather people perceive you as being kind,
smart or attractive?
 How do you like to receive care?
 How do you cope when things get hard?
 What do you really care about?
 What really frustrates you?
 What keeps you up at night?
 Who sticks out as being an early positive influence in
your life?
 Who is most important to you now? 
 How did you feel about where you grew up? 
  Was it a supportive environment?
 Who are you most like in your family?
 Who in your family do you struggle with?
 Is there a time when you did something that seems so
out of character that most people wouldn’t believe it? 
 What is the most trouble you’ve ever been in?
 Looking back on your life, who or what makes you
instantly light up?
 If you could leave a “mark on the world” that preceded
you, what would it be?
 What would you like to accomplish in life? 
 What makes your life feel purposeful? 
 What values are most important to you? 
 If one wish of yours could come true, what would it be?
 If you could travel anywhere, where would you go?
 If you could meet anyone in the world, alive or
deceased, who would it be?
 What brings you joy?
 What is the best piece of advice you've ever been
given?
Fun (sometimes funny) questions to ask friends
 What movie or show do you keep rewatching? 
 What makes you choose it? (See question above.)
 What was your favorite game as a child?
  Which book or movie impacted you most growing up?
 What’s your favorite childhood memory?
 What is your favorite memory?
 What is on your bucket list?
 What are two places you want to go before you die?
 What does your ideal friend weekend look like?
 What is the most exciting adventure you have been on?
 Where is the most awe-inspiring place you’ve ever
visited?
 If you weren’t in your current profession, what would
you be doing?
Hard questions to ask friends
 What is your worst memory?
 What fears do you experience? 
 What do you find most challenging in your life right
now?
 What is something that not many people know about
you? 
 What prevents you from sharing that part of yourself?
 How do you know when you can trust someone? 
 What event has had a large impact on your life?
 If you lost a loved one, do you think you would come to
me for support?
 If you lost your job, would you come to me for help?
  Have you ever stopped talking to a friend?
 Why did you stop talking to them? (See question
above.)
 Has a friend ever stopped talking to you?
 What led to that happening? (See question above.)
Personal questions about your friendship
 What about our friendship is important to you?
 What do you value most in a friendship?
 In what ways do you feel supported in the friendship? 
 In which ways do you not? (See question above.)
 In what ways do you feel trust within our friendship?
 What is your favorite trait in me?
 What’s your favorite part of our friendship?
 What do you most look forward to doing with me?
 What is your least favorite trait in me?
 What is one piece of advice you would give to me if you
knew I wouldn’t get offended? 
 What would you do if your partner didn't like me?
 What would you do if your parents didn't like me?
 Is there anything I can do to show my appreciation for
your friendship that I do not already do?
 What made it difficult to share? (See question above.)
 If we could only do one thing together before we die,
what would it be?