Questions to Ask a Friend You Haven’t Seen in a While

You’re seeing a friend you haven’t caught up with in months, maybe years. You want it to feel like it used to. What you don’t want is twenty minutes of “So, how’s work?” followed by a polite hug and the sense that you’ve both become people who exchange updates.

A list of good questions helps a little. What helps more is a short method: look at what was said last time, ask about the thing that was in progress, and then follow a thread instead of running an interview. The questions further down are grouped so you can use them that way.

Why a generic list isn’t enough

In a 2017 set of studies by Harvard researchers, people who asked more questions in a conversation were liked more by the person they were talking to. The type of question mattered. Of the kinds they counted, only follow-up questions predicted being liked more: ones that pick up something the other person has just said, like “I’m planning a trip to Canada” — “Oh, have you been before?” Questions that jumped to a new topic didn’t (Huang and colleagues, 2017).

Two honest limits. Those conversations were between strangers, online chats and four-minute speed dates, not old friends. And the authors themselves suspect there’s such a thing as too many questions, when one person asks and never offers anything back. A later critique challenged the speed-dating analysis; the authors re-ran it and stood by the result (Kluger and Malloy, 2019; Yeomans and colleagues, 2019).

Still, the idea carries over well. A follow-up question shows you were listening. With an old friend you can do something a stranger can’t: follow up on something they told you last time.

A three-step method

1. Look at what was said last time

Before you go, spend two minutes on what you know. What was happening for them when you last spoke? Who was new in their life? Did either of you say you’d do something? If you can’t remember, that’s normal; a note from last time is what fixes it. More on that below.

2. Ask about the thing in progress

The best openers are about something that was unfinished: the move, the renovation, the new job, the kid about to start school, the course, the recovery. Those questions have a built-in “since then”, and they tell your friend you remembered without you having to say so.

3. Follow a thread, don’t run an interview

One good question is enough to start. Then listen for the next one in their answer: “What happened next?”, “How did you decide?”, “What was that like?” Offer your own news in return, so it’s a catch-up and not a questionnaire. If you’ve brought five questions and use one, the catch-up went well.

From last time’s note to something to ask

Here’s how that looks with OldMate. Back in March, after a beer with Hamish before he left Melbourne, you said a quick note walking to the tram. OldMate kept who, where, his news, the thing to ask and what you’d promised:

Seven months later you’re driving up for the weekend. You open Hamish’s page. The promise you made is still there under Open commitments. Under Worth asking are the questions you chose to keep: tap Find something to ask and OldMate offers a few from what you’ve noted about him, and you keep the ones you’d actually ask and let the rest go.

Nothing on that page is sent to Hamish. It’s there when you open it, which is usually the night before or in the car park.

What to talk about when you catch up

These are grouped by where they sit in a conversation. Most are written with a gap for what you know about your friend; fill it in and they stop sounding like a list.

To open, without making it a quiz

• What’s been taking up most of your time lately?
• How’s [the thing they were starting] going?
• What’s been the best bit of the last few months?
• Are you still [doing the thing they loved]?

About the thing in progress

• Did [the move, the job, the trip] end up happening?
• How’s [their kid, partner or parent] finding [the new school, job or place]?
• What’s been harder than you expected?
• What’s the next step with [the project]?

Follow-up questions, once they’re talking

• What happened next?
• How did you decide?
• What was that like?
• What surprised you?
• Tell me more about [the thing they mentioned in passing].

Going a bit deeper

People tend to expect deep conversations to be more awkward than they turn out to be. In a series of experiments, strangers who talked about meaningful things felt less awkward and more connected than they’d predicted. With close friends and family, people’s predictions were more accurate, so use your sense of this particular friend (Kardas, Kumar and Epley, 2022).

• What’s been on your mind lately?
• What are you looking forward to this year?
• Is there anything you’ve changed your mind about since we last talked?
• What would you do with a free month?

About the two of you

• Do you remember [the trip, the share house, the night it all went wrong]?
• What do you miss from back then?
• Who do you still see from [school, uni, the old job]?
• When can we do this again? (If you set a plan, note it.)

Questions to handle gently, or skip

• Anything that may have changed. If you last heard about a partner, a job or a pregnancy a year ago, ask openly (“How’s everyone at home?”) rather than by name.
• Health and money. Let them raise it.
• “Why didn’t you call?” It’s rarely one person’s fault, and it starts the catch-up on the back foot.
• Every question on this page. Pick one or two.

If it’s been a long time

Getting in touch is often the hardest part, and it’s usually more welcome than it feels. In a series of preregistered experiments, people who sent a short message or small gift underestimated how much it was appreciated, and the gap was bigger when the message was more of a surprise or the two people were less close (Liu and colleagues, 2023). Those studies didn’t look at friendships that ended badly, so use your judgement there.

Mentioning something specific helps the message too: “Saw a shed on the drive and thought of you. Did the woodworking stick?” is easier to answer than “We should catch up!” There’s more on small check-ins in The Power of “Micro-Support”.

After the catch-up

The next catch-up starts with this one. On the way home, take two minutes to note what’s new for them, anything either of you promised, and one thing worth asking next time. That’s the whole habit; how to remember details about people goes into why it works, and what a personal CRM is covers whether you need an app for it at all. If you’d rather use a notes app or a spreadsheet, the personal CRM template has the same five lines.