Questions to Ask Your New Friends
Questions for someone you have only recently started spending time with: easy ground for a first coffee, and the ones worth saving until it is clear the friendship is going somewhere.
The questions
Open any question for the note
What's been keeping you busy lately?
Why ask it
A low-stakes opener that works anywhere. What they mention first, work, a project, their kids, tells you where their attention actually goes.
What could you talk about for an hour without getting bored?
Why ask it
Better than asking about hobbies because it licenses enthusiasm. People are noticeably more themselves while answering it.
How did you end up living here?
Why ask it
Almost everyone has a story, and it usually contains a job, a relationship or a family decision that is worth following up on.
What does a good Saturday look like for you?
Why ask it
Practically useful, because it tells you what to invite them to. It also shows whether they recharge alone or with other people.
What are you into that you're slightly embarrassed about?
Why ask it
Invites a small confession, which is how new friendships get past pleasantries. Offer yours first or it lands as a test.
What did you want to do when you were fifteen?
Why ask it
Easier and funnier than asking about ambitions now, and it often explains the job they ended up in.
What are you working on at the moment, in or out of work?
Why ask it
Present tense, so you have something specific to raise next time you see them. The in-or-out-of-work part also catches people whose real life is a side project rather than their job.
What's the last thing you got obsessed with?
Why ask it
More revealing than a favorite film, because it shows how they get interested in things rather than what they have already settled on.
Who do you know who's good at something unusual?
Why ask it
Gets them talking about their people, which is how you learn what their world looks like without asking about their friendships directly.
What have you changed your mind about?
Why ask it
Shows whether they can hold a position lightly. An answer that is entirely about other people being wrong is worth noticing.
What's the best advice you've been given, and did you take it?
Why ask it
The second half is what makes this worth asking. Advice everyone repeats and nobody follows says something about them either way.
What do you find hard that other people seem to find easy?
Why ask it
A quiet invitation to be honest, and it tells you what not to arrange: big groups, phone calls, early mornings.
What are you glad you did, even though it didn't work out?
Why ask it
Gets at how they judge their own decisions, and produces better stories than a question about achievements would.
How do you spend your time when you're on your own?
Why ask it
Distinguishes solitude they enjoy from solitude they endure, which matters if you are working out how often to get in touch.
What would you like to do more of but never get round to?
Why ask it
Practical, because this is where friendships actually form: the class or the gig neither of you would go to alone.
Who's had the biggest effect on how you think?
Why ask it
Deeper ground without being intrusive. Whether they name a parent, a teacher or a writer is informative in itself.
What do people usually get wrong about you?
Why ask it
Something most people have thought about and rarely been asked. Save it until you are past the first couple of meetings.
What's been the hardest year you've had?
Why ask it
Only worth asking once there is some trust. Too early, and you get a summary and an awkward pause rather than an account.
What do you need from a friendship?
Why ask it
Some people want weekly contact, others reappear happily after three months. Mismatched expectations here are what quietly ends new friendships.
What are you looking forward to?
Why ask it
A good closing question and easy to act on. Note the date, and ask how it went afterward.
Turning acquaintances into friends
Practical guidance for the conversation itself
How to ask
Answer your own question
Adult friendships form by trading, not by interviewing. Give your version before or straight after theirs.
Follow up on the detail, not the topic
If they mention a half-marathon, ask about the training and the bad week, not about running in general. Specific follow-ups are what make people feel heard.
Leave some questions unasked
Leaving something unasked is a reason to meet again. A conversation that covers everything can feel oddly finished.
Pacing
- First meeting: current life, how they got here, what they enjoy.
- Third or fourth: opinions, changes of mind, what they find difficult.
- Later: hard years, family, what they need from the people around them.
- At any point: a concrete invitation. Questions build interest, plans build friendships.
Where it goes wrong
The interrogation
Question after question with nothing given back feels like a screening. Two or three good ones per conversation is plenty.
Depth too early
Asking about someone's worst year in the first hour usually produces a flattened, polite answer and some regret on both sides.
Never converting talk into plans
Most new friendships die of scheduling rather than incompatibility. Suggest a specific day instead of saying you should do something sometime.