Catching up for real
- What is taking up most of your headspace lately?
- What is something good in your life you have not told many people about?
- Is there anything you are dreading this month?
- What is a recent win you have not celebrated properly?
- How are you sleeping, honestly?
- What are you looking forward to that has nothing to do with work?
- What is a small change you made recently that is working?
- Who have you been spending the most time with lately, and how is that going?
Our history
- What was your first impression of me, honestly?
- What is your favorite memory of us that I have probably forgotten?
- When did you realize we were actually friends?
- What is a time I was there for you that I might not have noticed?
- What is the funniest thing we have ever gotten into together?
- What is a trip we always said we would take and never did?
- How have I changed since we met?
Debates you have somehow never had
- What is the best decade for music, and you have to commit?
- Which of our friends would survive the longest in a horror movie?
- What is a popular opinion you strongly disagree with?
- Would you rather be rich and anonymous or famous and comfortable?
- What is the most overrated thing everyone our age loves?
- Is it ever okay to recline your seat on a plane?
- What is the best breakfast food, final answer?
The deeper ones
Best on a long walk or a late drive.
- What is something you have been struggling with that you have not said out loud?
- What is a dream you have been quietly working on?
- What do you think you need more of right now?
- Is there anything you wish I asked you about more?
- What do you think you will regret not doing in your twenties or thirties?
- How do you want our friendship to look in ten years?
- What is something you admire about yourself that you do not say enough?
- Is there a friendship you lost that you still think about?
How to use them
Pick the setting for the section. Debates are perfect for group dinners and car rides. The deeper ones need one on one time and a setting with no clock, like a long walk.
Ask the history questions on purpose. Hearing what a friend remembers about you, and how they saw you when you first met, is one of the most connecting conversations two friends can have, and most never have it.
Do not treat it as a checkup. You are not grading the friendship. If a question opens up something heavy, it is okay to just listen and stop there.
Questions people ask
Questions about shared history and private struggles do the most: their first impression of you, a time you were there for them, something they are dealing with but have not mentioned. Ask them one on one.
The debate section works best for groups: lighthearted arguments about music, food and hypothetical survival skills keep everyone talking and laughing without anyone feeling put on the spot.
Ask casually, at a natural moment, and make it clear they can answer briefly. Something like random question, but what is a dream you are working on lately feels like curiosity rather than an intervention.