You may know your best friend’s coffee order, worst haircut, and exactly which group chat they have on mute. You can know all of that and still have missed something: a worry they’ve been carrying for months, or a dream they stopped mentioning.
These questions give you a way to catch up on more than the week’s events. Start with whichever one you’d genuinely like to hear the answer to. Take turns answering, let either person pass, and follow an interesting answer instead of rushing to the next question. “What was that like for you?” can be a whole conversation.
Easy Ways In
A little reflection, a little imagination, and no need to open with your biggest secret.
- What’s something you’ve changed your mind about in the last few years?
- What’s a small thing that reliably makes your whole day better?
- Which compliment have you never forgotten?
- What’s something you’re quietly proud of that most people don’t know about?
- If you could be instantly great at one thing without practicing, what would you pick, and why that?
- Is there a place you feel attached to that other people might not think is special?
- What’s been taking up most of your headspace lately?
- What’s the best decision you made this year, even a tiny one?
- What song would play over the end credits of your last twelve months?
- What do you wish people asked you about more often?
About the Two of You
You have a shared history, but you may remember different turning points. There’s room here for both affection and an honest check-in.
- What do you remember about the first time we really talked?
- When did you know we were going to be close?
- What’s a moment from our friendship you think about more than I’d guess?
- What’s something I do that makes you feel cared for, even if I don’t realize I’m doing it?
- How can we make it easier to stay close when life gets busy?
- How do you think each of us has changed since we met?
- What’s one thing you think I’m too hard on myself about?
- When you’re having a rough time, what helps most from me: advice, distraction, company, or something else?
- Which tradition of ours would you fight to keep?
- If we’d met at twelve, do you think we would have been friends? Who would have gotten us in trouble?
Where You Came From
Ask about the people, small memories, and household rules behind the stories you already know.
- What’s something good from your childhood that you’d like to carry into your life now?
- What’s a rule from the house you grew up in that you still follow without thinking?
- Who was the adult you looked up to most as a kid, and do you still see them the same way?
- What did you want to be when you grew up, and is any piece of that still in you?
- What’s an ordinary childhood moment you can still picture clearly?
- What did you believe about adulthood that turned out to be completely wrong?
- When did you first feel like a grown-up? Really, not on paper.
- What would your younger self be thrilled to know about your life now?
- Is there something about the way you were raised that you’re still unlearning?
- What do you miss about who you used to be, and what are you glad you’ve grown out of?
Who You Are Right Now
Even a close friend can be working with an outdated picture of your life. These questions leave room for a new answer.
- What does a genuinely good day look like for you these days?
- What are you more confident about than you used to be?
- Which part of your life feels most like your own choice?
- Where do you feel most like yourself, and where do you feel like you’re performing?
- What do you keep doing out of habit that you’re not sure you still enjoy?
- How can you tell when you need a break?
- What’s a quality of yours that people tend to misunderstand?
- What’s the most “you” thing you own?
- If you could clear one thing off your plate tomorrow with no consequences, what would it be?
- What are you curious about lately?
Love, Family, and the People You Choose
Closeness takes more than one form. Follow whichever kind of relationship your friend wants to talk about.
- What did you learn about love from the relationships you watched growing up?
- What’s a small gesture that makes you feel especially loved?
- Which relationship, of any kind, changed you the most?
- What helps you trust someone enough to disagree with them?
- Is there someone you’ve lost touch with who you still think about?
- What’s a boundary you’ve set that you’re proud of?
- How has your relationship with the people who raised you changed as you’ve gotten older?
- What role, if any, do you want a romantic partnership to have in your life?
- Who brings out a side of you that I don’t often get to see?
- What do you want to give the people you love that you didn’t always get?
The Harder Stuff
Save these for a private moment when neither of you needs to rush. An answer doesn’t need a silver lining, and listening doesn’t have to turn into advice.
- Is there a fear you’ve outgrown—or one you’re still working on?
- Is there a choice you wish you could make again with what you know now?
- What’s been harder lately than you’ve let on?
- Has your idea of forgiveness changed over time?
- During a difficult time, what did someone do that actually helped?
- What do you worry people get wrong about you?
- Is there a decision you keep circling but haven’t made?
- What part of getting older scares you, and what part are you looking forward to?
- When you feel lonely, what kind of connection do you find yourself missing?
- What’s something you need to hear right now?
What You Want Next
Leave room for both the wildly impractical wish and the thing your friend might actually start next week.
- What would you do with a fully paid year off?
- Is there a dream you stopped talking about but still want?
- Where do you want to be in five years, in your life rather than on your résumé?
- What do you want to try before you feel ready?
- What kind of old person do you want to be?
- What’s one thing you’d like to have started by this time next year?
- What do you want more of that money can’t buy?
- What would make you feel like you’d lived well?
- Is there a place you’ve always wanted to live, even just for a month?
- Is there a goal you’d like company working toward?
For Very Late at Night
For when nobody’s checking the time and the conversation has gotten pleasantly philosophical. “I have no idea, but…” is a fine place to start.
- Do you believe some things are meant to happen?
- What do you think happens after we die, or what do you hope happens?
- If you could ask your future self one question, what would it be?
- What’s something you think about that you’ve never heard anyone else mention?
- What do you hope people say about you when you’re not in the room?