Reconnecting With Old Friends
For picking back up with someone you used to know by heart. Closes the gap without pretending the time didn’t pass.
Here’s how I use these: let someone pick the question they want to answer, and don’t rush to fill the silence after. The lists go from light to deep on purpose, so you can stop wherever the comfort runs out. The real magic isn’t the question — it’s getting curious about the answer.
The List
- Okay, catch me up. What’s actually new in your life?
- What’s something you’re into now that you weren’t back then?
- What’s a memory of us that still makes you laugh?
- What’s changed for you in the biggest way since we last really talked?
- What were you going through back when we drifted that I might not have known?
- Who are you now that past-you wouldn’t recognize?
- What’s something you’ve always appreciated about our friendship?
- What’s been the hardest year of your life since we last connected?
- What do you miss about how we used to be?
- What’s something you’re proud of building since then?
- What kind of friend do you need in your life these days?
- What’s a dream you’re still chasing or finally chasing?
- How can we keep this from going quiet again?
- What made you want to reconnect now?