21 Questions for Friends

What is your most embarrassing moment with me?

What is your favorite memory of our friendship?

What is something I do that annoys you?

What is your favorite thing about our friendship?

What is something you wish we did more often?

What is your funniest story about us?

What is something I have helped you with?

What is a secret we share?

What is something you have always wanted to tell me?

What adventure should we go on together?

When did you first realize we would be good friends?

What is something you admire about the people in this group?

What is your favorite inside joke we have?

What is a challenge you think we should do together?

If we could switch lives for a day, what would you do?

What is something you have never told anyone else?

What is a tradition you want us to start?

What do you think is unique about our friendship?

What is the first thing you thought when you met me?

What is one thing you think we both pretend to like?

What is the most trouble we have ever gotten into?

What is one thing you would do for me at 3 a.m. without asking why?

What is one thing you wish I would ask you for help with?

What is the best road trip or outing we have ever taken?

What is one thing you think we would be terrible at doing together?

What is one thing you think we would be unstoppable at together?

What is the hardest we have ever laughed together?

What is one thing you miss about how things used to be?

What is one thing you are excited about for our future?

What is one thing you would tell our younger selves about us?

What is the most supportive thing I have ever done for you?

What is the most supportive thing you have ever done for me?

What is one thing you think keeps our friendship strong?

What is one thing that almost ended our friendship?

What is one thing you forgave me for a long time ago?

What is one thing you hope I forgave you for?

What is the weirdest thing we both believe?

What is one opinion we will never agree on?

What is one thing you copied from me?

What is one thing I copied from you?

What is the best gift we have ever exchanged?

What is one thing you want to do together before we are old?

What is one thing you want to do together this year?

What is the most embarrassing thing we both witnessed together?

What is one secret you have kept for me?

What is one thing you know about me that no one else does?

What is one thing I know about you that no one else does?

What is the best advice you have ever given me?

What is the best advice I have ever given you?

What is one thing you think I underestimate about myself?

What is one thing you think you underestimate about yourself?

What is the most out-of-character thing you have ever seen me do?

What is the most out-of-character thing I have seen you do?

What is one thing you are proud of me for?

What is one thing you want me to be proud of you for?

What is one thing you think our friend group gets wrong about us?

What is the funniest misunderstanding we have ever had?

What is one thing you want to apologize for?

What is one thing you want an apology for?

What is the most generous thing you have ever seen me do?

What is one thing you want to plan as a surprise for me?

What is one tradition from our friendship you want to keep forever?

What is one inside joke you want to retire?

What is the best compliment I have ever given you?

What is the best compliment you have ever given me?

What is one thing you think we should defend each other from?

What is one thing you would never let me do without talking me out of it?

What is the longest we have ever gone without talking, and how did it feel?

What is one thing you want to know about my past?

What is one thing you want me to know about your past?

What is the most boring thing we somehow made fun?

What is one thing we should stop tolerating in other people?

What is one thing you think we both need to hear right now?

What is the best decision we made as friends?

What is one thing you want to celebrate about us?

What is one thing you think our kids will find funny about us someday?

What is one thing you want to be doing together in twenty years?

What is the most money you have ever spent on something stupid with me?

What is one thing you would move cities for — and would you for me?

What is one thing you think makes us different from other friend duos?

What is the best thing about having me as a friend?

What is the hardest thing about having me as a friend?

What is one skill you have always wanted to pass on to me?

What is one thing you want to learn from me?

What is one thing you are glad you never kept from me?

What is one thing you wish you had told me years ago?

What is the one story about us you tell everyone?

What is one story about us you will take to the grave?

What is one thing you want to do just the two of us, no group?

What is one thing you want to do with the whole group this year?

What is the bravest thing you have ever seen me do?

What is one thing you think I am afraid to try?

What is one thing you are afraid to try?

What is one thing you want us to be famous in our family for?

What is the most ridiculous thing we both take seriously?

What is one thing you think we should start a club about?

What is one thing you want to bet me on?

What is one thing you already know you will lose a bet about?

What is one thing you want to make up with me about someday when we are old?

What is one thing you want to remind me of when we are eighty?

What is one thing you think I should do before I die?

What is one thing you think we should witness together?

What is one thing you are thankful I talked you into?

What is one thing you are thankful I talked you out of?

What is one thing you want our friendship to look like in ten years?