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80 fun questions to ask your friends to get to know them on a deeper level

The next time you're bored with your besties, bust out these enlightening Qs.

Just when you think you know your best friend, they reveal something new. That — in and of itself — is the beauty of friendship.

But while some people may voluntarily offer up new intel, others may need to be prompted. In that case, Saba Harouni Lurie, ATR-BC, a licensed marriage and family therapist and founder of Take Root Therapy, suggests being intentional with the questions you ask.

"When we show vulnerability and offer care when another is vulnerable, we cultivate trust and strengthen our relationships,” she tells

Your friendship will be better for it in the long-run. "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

But let's get back to the specifics.

Antonia Hall, MA, a psychologist, relationship expert and author of "The Happy Human Playbook: A Practical Guide to Healing Body, Mind and Emotions With Joy and Pleasure," recommends questions that show another — perhaps, a new — side of your friend. Some thought-starters: Ask what they’re most grateful for or what their childhood was like.

Be mindful that you're not interrogating your friend, but simply giving them the ability to get more personal with (on their own terms, of course).

“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

While you may be inclined to focus on the present, find ways to look ahead to the future. In fact, Dr. Cynthia Shaw, a licensed clinical psychologist and owner of Authentically Living Psychological Services, suggests asking questions that hone in on your friend’s hopes and dreams.

We asked the aforementioned experts to share their best questions to ask friends, and compiled a list of our favorites below. Dedicate an entire night to this list, start with a few easy standouts or slowly chip away at the deeper questions when you're looking for something to do.

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 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

  • Describe your perfect day.
  • 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 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 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 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?