• What’s been on your heart and mind recently?

• What are your current priorities in this season of your

life, and why?
• How would you like people to experience you? What kind of
person do want to be in the world?
• 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
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?
• Did you grow up in an emotionally 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?
• Do you think other people see you the way you see yourself?
• What is the best piece of advice you've ever been given?
• Do you think you’ve met your soulmate?
• What is your earliest memory?
• What’s something small that feels sacred to you?
• When do you feel most like yourself?
• What role does joy play in your life these days?
• What’s a fear you’ve outgrown?
• Who in your life really sees you, and how do you know?
• What’s a memory you return to when you need grounding?
• What’s something you wish people asked you more often?
• What’s something small that brings you joy?
• If your younger self could see you now, what would surprise
them the most?
 • What’s a belief you hold now that you didn’t a few years
ago?
• What’s a way you show love that people might not always
notice?
• When do you feel most grounded or at peace?
• Who in your life makes you feel the most like yourself?
• Who is your severest critic?
• Do you think you’re kind to yourself?
• What daily rituals ground you?
• When do you feel calmest?
• What makes you anxious?
• What’s something that piques your curiosity that you’d like
to learn more about?
• Who’s the first person you’d call if you got good news?
• Who’s the first person you’d call if you got bad news?
• What qualities do you look for in a partner?
• What qualities do you look for in a friend?
Fun Questions to Ask Friends
• Describe your perfect day.
• What movie or show do you keep rewatching?
• What makes you choose that movie/show over and over again?
• 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?
• If you could have chosen your name, what would you have
picked?
• What’s your favorite unusual food combination?
• Do you prefer calls or texts?
• What’s one reality show you would consider being a
contestant on?
• If you could keep any animal as a pet, which would you
choose?
• 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?
• Who would you invite to your dream dinner party?
• Are you a dog person or a cat person?
• Who is your celebrity crush?
• What’s your biggest pet peeve?
• What celebrity do you secretly think you’d be best friends
with?
• Who is your biggest role model?
• If you could time travel to any era, which one would you
choose?
• Describe your ideal nap.
• What’s the most spontaneous thing you’ve done in your life?
• If you could master any hobby instantly, what would it be?
• What are you reading right now?
• What’s a favorite podcast of yours?
• Tell me what your perfect weekend morning looks like.
• Do you prefer swimming in a lake, ocean or pool?
• Are you a mountain or beach person?
• What’s the best meal of the day?
• If you were a drink, what would you be?
 • What’s the best concert you’ve been to in your life?
• Do you have a favorite band?
• What’s your favorite album?
• What is your go-to YouTube search?
• What’s your favorite way to exercise?
• What’s the best compliment you’ve ever received?
• What’s the weirdest compliment you’ve ever received?
• Do you like your eye color?
• What makes you cringe?
• Do you prefer the aisle or window seat?
• Do you have any secret talents?
• If you could have any superpower, what would it be?
• What’s your love language?
• If you could teach a workshop to people, what would be the
topic?
• What book is on your nightstand right now?
• Do you hit the snooze button or get up when the bell rings?
• What’s your guilty pleasure TV show?
• Tell me your favorite ice cream order.
• Do you snore?
• If I gave you $100 right now, what would you buy?
• What’s your signature sandwich order?
Hard Questions to Ask Friends
• What is the relationship with your parents like?
• 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 the end of that friendship? (See question
above.)
• What do you think other people notice first about you?
• What is your biggest regret?
• How long does it take to earn your trust?
• If you found money on the ground, would you keep it or look
for the owner?
• Do you remember your nightmares?
• What’s one bad habit you wish you could quit?
• What’s a value you were raised with that you’ve kept — and
one you’ve let go?
• What’s one part of your identity that feels really
important to you right now?
• What’s a risk you’re glad you took even if it didn’t turn
out the way you hoped?
• What kind of legacy, big or small, would you like to leave
behind?
• What do you wish people understood more about you?
• What’s a memory that makes you ashamed?
• Are there any risks in your life you regret not taking?
• What’s the most common reason you break off a relationship
in your life?
 • What’s something you wish you could apologize for, but
haven’t?
• Are there any bad habits you’re proud to have broken?
• What scares you the most right now in your life?
• What’s your biggest insecurity?
Personal Questions to Ask Friends
• 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 feel supported in our friendship?
• 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 do you dread doing with 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?
• Have you ever kept a secret from me?
• What made it difficult to share? (See question above.)
• If we could only do one thing together before we die, what
would it be?
• What does emotional safety look like in a friendship, for
you?
• How have I changed since we met?
• What’s one memory of us that always makes you smile?
• Is there anything you wish we did together more regularly?
• What’s something you want to ask me but never have?
• Have you learned anything from being friends with me?
• What’s the hardest thing you’d trust me to help you with?
• What’s something you hope never changes between us?
• What do you think our friendship will look like in five
years?
• Do I have any annoying tendencies I can work to improve?
• How would you describe our friendship to others?
• Do I remind you of anyone important in your life?
• Have I frustrated you recently?
• Do you feel like we see each other as much as you’d like?
• Are you happy with how frequently we communicate?
• Have I ever crossed a boundary that upset you?
• How do you think our communication styles differ?
• In what ways are we similar?
• In what ways are we different?
• When was the last time you were mad at me?
• What’s something I’ve done that made you grateful that I
may not know about?
• Would you feel comfortable introducing me to your family?
• Would you feel comfortable introducing me to your partner?
• When was a time you felt betrayed in our friendship?
• When was a time you felt loved in our friendship?
• Do you have a favorite thing we do together?
• Do I initiate contact enough?
• Do you have any friends you wish I could meet because you
think we’d get along really well?
• Do you think we resolve disagreements well?
• When was the last time I made you laugh really hard?
• When was the last time I hurt your feelings?
• What do you think a fun tradition we do together could be?
• When did you first realize we were going to become friends?