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105 deep questions to ask

friends to get to know them
better
Take your friendship to a whole new
level with these conversation starters.

I missed my friend's birthday. …

00:37 / 06:44

Jan. 5, 2023, 9:07 PM GMT+1 / Updated April 18, 2024, 6:17

PM GMT+1

By Sarah Fielding and Sophie

Caldwell

When you first meet someone new, you

often ask them a multitude of questions:
where are you from? What do you do for
work? Do you have any pets? What do
you do in your free time?

These are all solid conversation starters

to learn more about a casual
acquaintance, but there's a limit to how
well you can get to know someone
through surface-level chats.

Asking thoughtful questions is a surefire

way to solidify and deepen your
relationships, whether you're new pals or
childhood besties.

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In our longer friendships, we may forget

to continue asking meaningful questions
since we already know the other party so
well.

You may know your best friend’s favorite

shows, meals, songs and movies by heart,
but how much do you know about their
thoughts, memories and dreams?

“There is no such thing as knowing

everything about a person, so ongoing
connection building between friends
helps to nurture and grow the
relationship, especially through natural
and unnatural life transitions,” Leanne
Leonard, a licensed marriage and family
therapist at Mindpath Health, tells
TODAY.com.

Ultimately, demonstrating curiosity about

your friend's inner world shows them that
you care about their thoughts and
feelings. In the long run, this open
dialogue will make it easier for them to
turn to you during tough times.

"Healthy communication helps create a

foundation of safety, trust, and respect for
each other, which in turn fosters an
environment of openness and
vulnerability," Jodie Milton, relationship
and intimacy coach at Practical Intimacy,
tells TODAY.com.

We asked experts to weigh in on the best

questions to get to know your friends
better. From lighthearted to personal,
these deep questions will help you build
even closer bonds with your inner circle.

Deep questions to ask

friends

• 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?

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?

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?

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 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?

• 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 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.)

• What qualities do you look for in a

partner?

• What qualities do you look for in a

friend?

• If we could only do one thing

together before we die, what would
it be?

Even more questions for

friends
• 105 'most likely to' questions to strengthen
conversations

• 90 funny questions for LOL-worthy

conversations

• 100 this-or-that questions to make your

conversations more compelling

Sarah Fielding
Sarah Fielding, MS, is an acclaimed
journalist focusing on mental health, gender rights,
and social issues. She's also the co-founder
of Empire Coven, a space for highlighting
trailblazing women across New York. She has
written for The Washington Post, The New York
Times, Insider, Verywell, The Guardian and more.

Sophie Caldwell &

Associate Lifestyle Reporter

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