Questions to Ask When Catching Up
For anyone about to meet or call a friend, relative or former colleague they haven't spoken to in months or years, and who wants something better than 'so, what's new?' The 51 questions follow the conversation as it tends to go: the first minutes, what changed, work and home, hard news, old times and looking ahead. Each has a note on what a good or a worrying answer sounds like and what to do with it, including the subjects that may have gone badly since you last talked.
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The questions
Each question, and why to ask it
First minutes
What's the headline since we last talked?
Why ask it
Asking for a headline lets them choose one thing instead of summarizing months or years on the spot. Whatever they lead with is what is on top for them right now, so stay there for a while before you move on. If you get 'oh, not much', give your own headline first and ask again.
What does an ordinary week look like for you now?
Why ask it
A week is small enough to describe, and it tells you more than a list of events would: who they see, how long they work, whether there is any slack in it. Pick the detail that sounds new, like a Tuesday class or a long commute, and ask about that.
How long has it actually been, and what was going on the last time we saw each other?
Why ask it
Pinning down the last meeting gives you both a starting line, and you will often disagree about the year, which is a good first laugh. From there, 'and then what happened?' is all the question you need.
What's been making you happy lately, big or small?
Why ask it
'Big or small' is the working part: someone in the middle of a rough year can still say the dog, a show or a decent tomato sandwich. If they can't think of anything at all, don't push. Remember it, and ask how they are really doing once the two of you have warmed up.
Are you still in the same place, or have you moved?
Why ask it
A plain fact is easy to answer, especially on a phone call where you can't read a face. Behind most moves there is a reason, such as a job, a person, the rent or a parent who needs help, so 'what took you there?' usually opens the real story.
How much time do you have: a quick coffee, or the long version?
Why ask it
Knowing whether you have twenty minutes or the whole afternoon tells you which questions to ask and which to save. It also spares you both the moment when a big subject opens up just as one of you has to leave.
Who do you spend most of your time with these days?
Why ask it
Safer than asking after a partner by name when you can't be sure they are still together. The people they list are the ones in the picture now. If a name you expected never comes up, leave it for the moment and let them tell you in their own time.
What did I miss that you wish I'd been around for?
Why ask it
It admits the gap instead of pretending there wasn't one, and it leaves room for a wedding as much as a funeral. A breezy 'nothing, really' is a fine answer. If they do name something, that is your conversation, and 'I'm sorry I wasn't there' is worth saying if it's true.
What changed
What's in your life now that I don't know about yet?
Why ask it
Wide on purpose: a puppy, a partner, a house and a diagnosis are all answers to it, so they decide whether to start with the good news or the hard news. Ask how the new thing arrived, because the story of how it happened is nearly always better than the fact.
Have you been anywhere good since I last saw you?
Why ask it
Trips are easy ground after a long gap, and they come with photos, so ask to see two or three. A weekend at a lake counts as much as a month abroad. If they say they haven't been able to get away, ask where they would go first, and hold back your own vacation list.
What's your newest hobby or obsession, and who got you into it?
Why ask it
The friend who hated running now does trail races, and the one who lived on takeout bakes bread. Tease a little if that was always your way with each other. The second half of the question does more work than it seems to, since a new interest usually arrives with new people and a new routine.
Is there anything you've quit or let go of in the last few years?
Why ask it
What people stop rarely makes the highlights, whether it is a job, a sport, a habit or a city, and it often explains more than the additions do. Listen for whether the stopping was their choice. A layoff or an injury shows in the tone, and the tone tells you whether to say 'good for you' or 'I'm sorry.'
Have you changed your mind about anything big over the years?
Why ask it
Best after a gap of years. Children, city life, a career or a faith are common answers, and some will surprise you. A first conversation back is no place to argue with the new view, so ask what changed it and hear the whole answer.
What about you hasn't changed one bit?
Why ask it
Hearing that someone still supports the same hopeless team or orders the same terrible coffee is as comforting as any news. Offer a guess of your own first ('tell me you still alphabetize your spices') and it becomes a game.
What would you call the chapter of life you're in right now?
Why ask it
A playful frame for a long gap. A title like 'the recovery year' or 'finally settled' gives you the mood in three words, and asking what the chapter before was called gets you the backstory without a timeline.
What have you been watching, reading or listening to that I should know about?
Why ask it
Light enough to send by text, and useful in person when the bigger subjects have run heavy. Take the recommendation seriously: a message a week later to say you tried it is the easiest way to turn one catch-up into regular contact.
What's the biggest decision you've had to make in the last year or so?
Why ask it
They set the scale, so it might be a marriage or it might be finally selling the car. Pay attention to whether they sound settled or are still arguing with themselves. Someone still arguing wants to think it through with you, not be congratulated.
What are you proud of from the last couple of years that never made it online?
Why ask it
A social feed makes people feel caught up when they've only seen the photos that were posted. The unposted answers tend to be quieter: getting through a hard year, a child's turnaround, a debt paid off. Say 'I'm glad you told me' and mean it.
Work and home
Are you still doing the same work, or has that changed?
Why ask it
This is the safe wording when you can't be sure the job you remember still exists. Asking 'still at' a company by name can land squarely on a layoff. If things have changed, find out whether the change was their idea and take your tone from that.
How do you feel about work these days: into it, putting up with it, or looking around?
Why ask it
Three options make an honest answer easy, where 'how's work?' gets 'busy'. From a former colleague, 'looking around' is an opening. Ask what they are looking for, and offer an introduction only if you can really make one.
What's it like there now, compared with when I left?
Why ask it
For a former colleague who still works at the place you left. You will hear who was promoted, what was reorganized and which old complaint finally got fixed. Enjoy it without crowing or pitying: they are still there, and 'sounds like you've made it work' is kinder than 'I got out just in time.'
Do you still hear from anyone at the old job?
Why ask it
This is how news of everyone else gets traded between former colleagues. Pass on what is public, like a new job or a move, and keep back anything that was told to you in confidence. If the talk turns to running someone down, change the subject: you came to see this person, not to review the others.
How's everyone at home?
Why ask it
'Everyone at home' assumes no partner, no children and no particular arrangement, so they get to define the household for you. Someone you remember may be missing from the answer. Wait: they have chosen not to bring that person up yet, and they may later.
How are the kids, and what are they into right now?
Why ask it
Only for someone you know has children. Asking what they are into gets you stories about dinosaurs or drum kits, where 'how old are they now?' gets a number. Never ask someone without children whether or when. If it matters to them, they will raise it.
How are your parents doing?
Why ask it
After a long gap a parent may be ill, may need daily care or may have died, so ask it in a quiet moment and not as a throwaway. If the news is bad, 'I'm so sorry, I didn't know' is enough. Then let them decide how much more to say.
Is there anyone in your family I should be asking about?
Why ask it
An honest question when you've lost track of who married, who was born and who is gone. It hands them the list, so you don't have to guess at names. Write down what you learn afterward, because remembering it next time is what counts.
How much of your time is your own at the moment?
Why ask it
It gets at long hours, small children and caring for a relative without asking about any of them directly. 'None' said with a laugh is ordinary busyness. 'None' said flatly is someone stretched thin, and a small concrete offer, like bringing dinner over, is worth more than a sympathetic noise.
Hard news
That's the news. How are you actually doing?
Why ask it
Save it until the news has been traded, and ask only if you have time to hear the answer. A long pause before they speak usually means there is one. If they say 'fine' a second time, accept it: you have shown that the door is open, which was the point.
I heard a little about what happened. Do you want to talk about it, or would you like a break from it?
Why ask it
For a divorce, a death or a lost job that reached you secondhand. Saying you know saves them from wondering whether you do, and the either-or lets them choose. Plenty of people are tired of telling the story and will take the break gratefully. Believe them.
Was there a rough patch in there that I never knew about?
Why ask it
Some people will not volunteer a bad year but will confirm one if asked. If the answer is yes, 'do you want to tell me about it?' is kinder than asking for details. Should they say they wished you had called, don't defend yourself. Say you wish you had too.
How's your health been, if you don't mind my asking?
Why ask it
Use it when they have mentioned being ill or you already know they were. A short 'fine, thanks' is a boundary, so respect it. If they do open up, resist advice and stories about someone else's illness, and ask what a good day looks like for them now.
What's turned out to be harder than you expected?
Why ask it
Made for changes that look good from outside: a new baby, a promotion, retirement, a move to somewhere beautiful. Reassuring too quickly shuts the subject. 'That sounds hard' keeps them talking, and 'but you're doing great' ends it.
What helped you get through it?
Why ask it
The follow-up once hard news is on the table. It moves the talk from the event to the people and habits that held them up, which is easier ground and often the part they want to tell. If the answer is 'nothing, I just got through', say you'd like to be someone they call next time.
Is there anything you'd rather we stayed off today?
Why ask it
Easier to put in the message that sets up the meeting than to say across a table, and a friend who has been through something often answers with relief. Whatever they name, leave it alone unless they bring it up themselves, and don't ask why it is on the list.
Did I drop the ball on staying in touch, or did we both just get busy?
Why ask it
If the silence has been bothering you, name it once. The usual answer is 'both, don't worry about it', and then the guilt is out of the room. If they say they were hurt, listen and apologize without listing your reasons.
Old times
What do you remember about how we first met?
Why ask it
The two versions never quite match, and comparing them is the fun. Reach for it when the conversation still feels a little formal, because it reminds you both why you became friends in the first place. With a relative, ask for their earliest memory of you instead.
Which story about us do you still tell, and how much has it grown?
Why ask it
Everybody has one on rotation. Let them tell it all the way through even if you were there, then supply the details they have improved over the years. The gap between the two tellings is half the entertainment.
Who from the old days do you wonder about?
Why ask it
You trade names, and sometimes one of you has real news of the person. If the name that comes up is someone either of you fell out with, or someone who has died, keep it short and kind. Otherwise, sending that person a photo of the two of you makes a good ending to the day.
What did we think was a huge deal back then that makes you laugh now?
Why ask it
Think of the exam, the breakup or the boss that once kept you both awake. Laughing at the old emergencies is a way of noticing how far you have both come without anyone making a speech about it. To bring things back to the present, ask what today's version of that worry is.
Is that place we always went still there?
Why ask it
Every friendship had a headquarters, whether it was a diner, a park bench or the office kitchen. If one of you has been back, you get a report on what has changed. If it is still open, you have just found the venue for next time.
What did you think I'd end up doing, and how wrong were you?
Why ask it
Their old prediction of you is usually funny or flattering, and it turns the talk toward your life without you having to start it. Share your own prediction for them only if it is kind. 'I always knew you'd leave that town' lands better than 'I thought you'd be famous by now.'
Which of our old jokes would still work, and which should stay buried?
Why ask it
An in-joke that still gets a laugh shows the two of you have kept a shared language. One that needs explaining has run its course, so let it go quietly. With luck the afternoon produces a new one to replace it.
Is there anything from back then you've wanted to say and never did?
Why ask it
Keep it for late in the conversation, when the ease is back. What comes out is often a thank-you, sometimes an apology or a confession about who really broke the lamp. If it is an old grievance, hear it without reopening the case, since being heard may be all the person wanted.
Looking ahead
What's coming up for you that you're excited about?
Why ask it
Listen for anything with a date on it, such as a trip, a due date or a race. Put it in your phone and send a message that week. A text that says 'isn't it today?' shows you were listening.
What are you hoping will be different by the time we next talk?
Why ask it
It frames their goal against your next conversation, which quietly assumes there will be one. Answers run from 'a new job' to 'sleeping through the night'. Ask about it by name when you do next talk.
What do you keep saying you'll do once things calm down?
Why ask it
Things rarely calm down, and they know it, so expect a rueful laugh before the answer. If the plan is something the two of you could do together, such as the trip or the class, propose a month before the subject changes.
Are you planning to stay put, or is a move on the horizon?
Why ask it
Practical for the friendship, because it tells you whether seeing each other is about to get easier or harder. An unsure answer often points to a bigger open question about a job, a relationship or a parent. 'What does it depend on?' is the gentle way in.
Is there anything you're working on right now that I could help with?
Why ask it
Ask only if you mean it. For a former colleague that might be an introduction, a reference or a second pair of eyes on a resume, and for a friend a lift, a spare room or a free Saturday. If they say no, leave it there, because offering twice turns help into pressure.
How do you like to stay in touch: calls, texts, voice notes, or a proper visit twice a year?
Why ask it
One person hates the phone and the other never checks messages, and a mismatch like that can keep two people silent for years without any falling out. Settle on the form the busier of you can keep up.
When should we do this again, and can we pick a date right now?
Why ask it
'We should do this more often' goes nowhere without a date attached. Get the calendars out before the bill comes or the call ends. If they hesitate, offer something looser, like 'I'll text you the first week of next month', and then do it.
What's the one thing I should check in on next time?
Why ask it
They will name the interview, the test results, the kid's tryout, whatever is unresolved today. You leave with a ready-made first question, and with a reason to write sooner if the date they mention comes before you next meet.
How to catch up without it feeling like an interview
Practical guidance for the conversation itself
Before you call or meet
Check what you already know
Reread your last messages and think back to what they told you then: the job they were applying for, the parent who was unwell, the name of the partner. Then hold all of it loosely. A year is long enough for any of it to have changed, and a social feed shows only what someone chose to post.
Say the gap out loud, once
One sentence does it: 'I can't believe it has been three years, and I'm glad we're doing this.' A long apology for not calling makes the other person spend the first ten minutes comforting you. If the silence needs more than a sentence, there is a question for that under Hard news.
Bring your own headline
Decide beforehand what you'd say if asked how you have been, including one thing that has not gone well. A catch-up is a trade, and a person who hears only good news from you will tend to give you only good news back.
Choose a setting that fits the gap
After a very long silence, pick something with a natural end, like a coffee, a walk or a call with a stated length. It takes the pressure off both of you. If it goes well, you can always order another round or stay on the line.
How the conversation tends to go
Wide first, then follow
The First minutes questions are open on purpose, so the other person picks the subject. Once they have picked, stay on it. Three follow-ups on one piece of news tell someone you are interested, and ten fresh questions in a row tell them you came with a list.
Trade, don't interview
Answer your own question after they have answered it, and keep your version a little shorter than theirs. If you notice you have asked four questions without offering anything, stop and tell them something about your own year.
Work and family without prying
Use the open wording: 'still doing the same work?' in place of a company name, 'everyone at home' in place of a spouse's name. Jobs, marriages, pregnancies and plans for children are the subjects most likely to have changed, and the open version lets them tell you so without having to correct you.
Use old times as a bridge
Shared memories bring the ease back quickly, which is why they come after the news and not before it. An hour spent only on the past, though, leaves you knowing nothing about the person in front of you. Tell one or two stories, then ask what today's version of that looks like.
End on the next one
The Looking ahead questions are there so the conversation does not finish on 'we should do this more often.' Leave with a date, or at least with who is texting whom and when, and with one thing to ask about next time.
When the news is bad
If you step on something
You ask after a husband and learn there was a divorce, or after a mother who died in the spring. Say 'I'm so sorry, I didn't know' and stop there. Explaining why you didn't know, or apologizing at length, turns their loss into your embarrassment.
Let them set the depth
Some people want to tell the whole story and some are worn out by it. 'Do you want to talk about it, or would you like a break from it?' covers both. Take the answer at face value and don't circle back later to check.
Listen before you fix
Advice, silver linings and the story of someone you know who went through the same thing can all wait. What an old friend can offer is attention, and a memory of who the person was before the hard thing happened. If what you hear worries you, say so plainly and ask who they have around them. You do not have to solve it over coffee.
When your news is the hard part
If you are the one with the divorce or the layoff, decide in advance how much you want to say, and say it early in a sentence or two. It stops the other person tiptoeing, and it stops you from dreading the question all afternoon.
When their good news stings
They got the promotion in the year you lost your job, or they are expecting and you have been trying. Congratulate them properly and ask one real question about it. You can be glad for them and sad for yourself at once, and you don't owe anyone an account of the second part unless you want to give one.
Friend, relative or former colleague
An old friend
Almost everything here works. Lean on What changed and Old times, and don't be alarmed if the first quarter of an hour feels stiff: it is two people finding the old rhythm again. One shared joke is usually enough to bring it back.
A relative
Family news travels secondhand, so you may know more about a cousin than the cousin has told you. Don't quote the grapevine back at them. Ask the open question and let them give their own version, which is often different from the one that reached you.
A former colleague
Stay mostly in Work and home and Looking ahead. If you are getting in touch because you want something, such as a reference, an introduction or advice about a job, say so in the invitation and again early in the conversation. Most people are happy to help and less happy to discover the reason at minute forty.
By phone, video or text
On a call you cannot see a face fall, so favor the plain questions and listen to the pauses. Choose three or four questions, not twenty. By text, send one question at a time and make it an easy one, such as what they have been watching, and keep the heavier ones for when you can hear each other's voices.