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 Questions
Warm Up
- What is the best thing that has happened to you since we last really talked?
- What is something you are into now that you were not back then?
- What is your favorite memory of us?
- What is something that still makes you think of me?
- Who from back then do you still talk to?
- What is the funniest thing we ever got in trouble for?
- What song reminds you of us?
- What is the best adventure we had together?
- What do you do for fun these days?
- What about you has not changed at all?
Get Real
- How have you changed since we were close?
- What has been the hardest part of the last few years for you?
- What do you miss most about how things used to be?
- What is something you wish you had told me back then?
- What does a good friend look like to you now?
- What is a big life moment I missed?
- Who has been there for you since we drifted?
- What are you proud of from the last few years?
- What have you been through that changed you?
- What do you need in a friendship now that you did not before?
Go Deep
- Why do you think we drifted?
- Is there anything you have been holding onto about our friendship?
- What did our friendship give you that you still carry?
- What would it look like to be in each other’s lives again?
- What do you want me to know about who you are now?
- Did you ever want to reach out and not know how?
- What did you feel when you heard from me?
- Is there anything you want to say sorry for, or hear sorry for?
- What do you value most about who we were together?
- What is one small way we could stay in touch?