50 Questions To Ask Your Best Friend

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50 Questions To Ask Your Best Friend

How well do you really know your bestie? Find out the most fun, juicy, personal, and interesting facts about your bff with these 50 questions to ask your best friend.

questions to ask your best friend

“The typical expression of opening Friendship would be something like, ‘What? You too? I thought I was the only one.’…But as long as each of these percipient persons dies without finding a kindred soul, nothing (I suspect) will come of it; art or sport or spiritual religion will not be born. It is when two such persons discover one another, when, whether with immense difficulties and semi-articulate fumblings or what would seem to us amazing and elliptical speed, they share their vision—it is then that Friendship is born. And instantly they stand together in immense solitude.” – C.S. Lewis

Whether it’s a rather new friend or you go way back, they’re your best friend for a reason. You might share a special connection, lifestyle, or experience. They’re the person you trust with your secrets, have the most fun with, and of course the best conversations with. But how well do you really know your bestie? If you haven’t already, make sure to check out the 50 questions to ask your best friend below and ask them the next time you hang out with your girl. By doing so you’ll strengthen your bond and discover new parts of each others’ personalities.

Make sure to bookmark this post for easy access or save your favorite questions in the notes of your phone.

Of course, you’re not supposed to interrogate your friend and ask all the questions at once. But you know them best. Some of us are an open book and would talk for hours about ourselves, others need the right circumstances and conversation starters to open up.


Friendship is all about growth, fun, and support. By asking the right questions and finding out more about your bestie, you will not only feel more connected but also learn how to better support them and comfort them when needed. And they will do the same for you. So stay curious about each other and keep discovering new parts of your bff as you go through life’s challenges, it’s ups and downs.

“And what is a friend? More than a father, more than a brother: a traveling companion, with him, you can conquer the impossible, even if you must lose it later. Friendship marks a life even more deeply than love. Love risks degenerating into obsession, friendship is never anything but sharing.” – Elie Wiesel

50 Questions To Ask Your Best Friend

#1 What’s one book that changed your life?
#2 What is your biggest fear?
#3 Who is your role model?
#4 What’s your favorite childhood memory?
#5 What’s your biggest insecurity?
#6 Have you ever lied to me?
#7 Is there anything I have or do that you’re jealous of?
#8 Do you believe in God?
#9 Do you pray?
#10 Do you believe once a cheater, always a cheater?
#11 What’s something that I’m doing that annoys you?
#12 Are you happy?
#13 Have you ever struggled with your mental health?
#14 What are you most looking forward to each day?

“A good friend is a connection to life — a tie to the past, a road to the future, the key to sanity in a totally insane world.” – Lois Wyse

#15 What’s your proudest moment?
#16 What’s one conspiracy theory you actually believe?
#17 Who was your first kiss with?
#18 What was your first heartbreak?
#19 If you could change one thing from your past, what would it be?
#20 Are you confident in your body?
#21 What do you value most in friends?
#22 Do you journal?
#23 What do you feel the most guilty about?
#24 When do you feel the most alone?
#25 Have you ever participated in a protest?
#26 What’s the nicest thing someone has done for you?
#27 Who is someone you wish you could apologize to?
#28 What is your definition of success?
#29 What advice would you give to your younger self?
#30 What’s one thing you would change about yourself right now?
#31 What makes you sad?
#32 What stresses you out the most?
#33 How do you cope with disappointments
#34 What’s the biggest leap of faith you’ve taken?
#35 Do you think you’re hard on yourself?
#36 Do you believe in love at first sight?
#37 If you could have one superpower, which would it be?
#38 How will you know you’ve “made it”?
#39 Would you like to be famous? Why, why not?
#40 What’s one surprising fact about you?
#41 What luxury item would you splurge on?
#42 What are you putting off right now?
#43 Which celebrity would you want as your BFF and why?
#44 What do you consider your best physical feature?
#45 What’s the first thing you do when you wake up in the morning?
#46 Have you ever been addicted to something?
#47 What has been your favorite travel memory so far?
#48 What’s your most delusional goal/dream?
#49 What do you think about manifestation?
#50 If you could only have three things on your life bucket list, what would they be?

Have fun finding out the most fun, personal, and random facts about your best friend. Stay curious, stay open-minded, and be understanding. Instead of engaging in gossip or limiting your conversations to small talk and catching up about the kids, make sure to also take the time to get to know each other better. There is always more to a person than we might think. More to discover than we already know. Deepen your bond and have a good laugh while asking the questions presented in this post.

“One friend with whom you have a lot in common is better than three with whom you struggle to find things to talk about. We never needed best friend gear because I guess with real friends you don’t have to make it official. It just is.” – Mindy Kaling

50 Questions To Ask Your Best Friend