Questions to ask your best friend
Friendships rarely end. They drift, one missed call at a time. These are for staying in each other's lives in the small ways: what's actually going on at work, the opinion you've never shared, the thing from years ago you both still laugh about.
Send one in the group chat, or one a day to the friend you keep meaning to call.
Catching up
- 1What's the most you thing you've done this week?
- 2What's taking up the most space in your head right now?
- 3What's something good that happened that you haven't told anyone?
Our history
- 4Which memory of ours would you put in a museum?
- 5What's the first thing you remember about meeting me?
- 6What's a phase of my life you're glad you witnessed?
Opinions
- 7What's a hill you'd die on that I'd disagree with?
- 8What's the most overrated thing everyone likes?
- 9What's a widely disliked thing you'd defend?
The real stuff
- 10What's something you're working through right now?
- 11What do you need from your friends that you don't ask for?
- 12When did you last feel lonely in a room full of people?
Work and money
- 13What part of your work actually satisfies you?
- 14What would you do if money didn't matter?
- 15What's the worst job you've ever had?
One of these, every morning, for the two of you
Stitch sends you and your person the same question each day. You each answer on your own, and neither of you sees the other's answer until you've both written yours. Then you see them side by side. It takes about a minute.
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Play
- 16If we started a business together, what would it be and how would it fail?
- 17What's my most predictable trait?
- 18Which of us would last longer in a survival show?
The future
- 19Where do you want to be living in five years?
- 20What's a trip you want to take that nobody's said yes to?
- 21What's on your list for this year that hasn't happened?
Friendship itself
- 22What makes someone a good friend to you?
- 23How do you know when you can trust someone?
- 24What's the friendship you're most proud of?
The small stuff
- 25What's the last thing you saved a photo of?
- 26What's the best thing you've watched recently?
- 27What's the song of this month for you?
Deeper cuts
- 28What do you think happens after we die?
- 29What's the closest you've come to a religious feeling?
- 30What's the best decision you've ever made?
How to get honest answers
- Both of you answer.A question only one person answers is an interview.
- Answer before you hear theirs.Otherwise the second answer is mostly a reaction to the first.
- One at a time.One good question a day beats thirty in a row. The list will keep.