‘How are you?’ is a perfectly good question. It’s also a big one. When you haven’t seen a friend for a while, it can leave both of you trying to compress months into ‘Good, busy.’ A more specific question gives the conversation a smaller door to walk through.

Ask about a piece of their day

You don’t have to open with the biggest thing in someone’s life. Ask about something they’ve noticed, enjoyed, or spent time on. Small details can make an ordinary week easier to picture.

  • What’s been taking up more of your attention than you expected?
  • What’s a small thing that made your week better?
  • Have you found anything lately you immediately wanted to recommend?
  • Which part of your day do you most look forward to?

Give an old story a new angle

With longtime friends, you already share a lot of history. That doesn’t mean you remember it the same way. Pick a memory you both enjoy, then ask for the detail you never heard.

  • What do you remember about the first time we met?
  • Which of our old plans would you still be up for?
  • What’s a story from that time that I somehow missed?

Leave room for a real answer

If a friend gives a short answer, let it be short. They might be tired, distracted, or just more interested in another subject. Offer your own answer too, so the conversation has somewhere to go without putting all the attention on them.

For a group, try a question everyone can answer briefly: ‘What’s something you changed your mind about lately?’ There’s no need to go around the table or insist that everyone joins in.

  • What’s something you’re looking forward to that isn’t on your calendar yet?
  • Is there anything you wish you had more time for?
  • What would you like our next catch-up to look like?

Follow the interesting part

The best part of a catch-up may be a passing comment. If your friend mentions a new hobby, an odd encounter, or a surprisingly good lunch, you can stay there. You don’t need another prompt just because you have one ready.

A coffee can be a good catch-up even if you never cover the major updates. Sometimes you just want to spend an hour in each other’s company.