105 Deep Questions to Ask Your Friends

Publish date: 2024-07-25

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.

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