Questions to Ask to Get to Know Someone
Questions for the middle stretch of a conversation with someone new, ordered from easy openers to the ones worth saving until you have both relaxed. Written for first dates, new colleagues, and long car journeys.
The questions
Open any question for the note
What have you been up to lately, outside of work?
Why ask it
A low-stakes opener that still avoids what do you do. People answer with whatever is genuinely occupying them, which hands you three threads to pull rather than a job title.
What are you weirdly good at?
Why ask it
Asks for a specific skill rather than a personality summary. The answers people offer, parallel parking, accents, remembering birthdays, are almost always a story in disguise, so follow up rather than moving on.
How did you end up doing what you do?
Why ask it
Asks for a path instead of a role. Most careers turned on an accident or a person who intervened, and that is the part worth hearing; a two-word answer usually means they are bored of their job, not of you.
What is taking up most of your head space at the moment?
Why ask it
Catches them where they actually are today rather than in general. A deflection here is worth respecting, and a real answer moves the conversation forward faster than any icebreaker.
What did you want to be when you were twelve?
Why ask it
Safe to answer and revealing to compare against the present. The good follow-up is whether anything of that answer survives in what they do now, which people often have not thought about.
Where did you grow up, and how much of it stuck?
Why ask it
Two questions in one, and the second half does the work. What someone kept from a place, or deliberately shed, tells you about family and distance travelled without asking about either.
What is the best thing you have read or watched this year?
Why ask it
Recommendations are easy to give and hard to fake. What someone actually finished this year is more informative than a favourite film of all time, which is usually a decade out of date.
What do you do on a Sunday when nothing is planned?
Why ask it
Unstructured time shows preferences that scheduled time hides. Someone who cannot describe an empty Sunday is telling you something real about the shape of their life right now.
Who do you talk to most?
Why ask it
Gets to their people without asking about relationship status or family. Whoever gets named first is generally the centre of their week, and the reason why is the better half of the answer.
What have you changed your mind about?
Why ask it
Asks for revision rather than conviction, which keeps it well clear of an argument. People who cannot name anything they have revised are usually not enjoying being asked questions at all.
What is a rule you have for yourself?
Why ask it
Personal rules are specific and quotable: never eat lunch at the desk, always ring back the same day. They describe someone's values without either of you using the word.
What do people usually get wrong about you?
Why ask it
Invites the gap between how someone comes across and how they feel, and people frequently answer with something they have been waiting for an opening to say.
What is the best advice you have been given, and did you take it?
Why ask it
The second half is what makes this work. Advice everyone quotes and nobody follows is a more interesting subject than the advice itself, and it is where the honesty arrives.
What are you saving up for, in money or in time?
Why ask it
Phrased so it works whatever their situation. What someone is deferring for reveals priorities more reliably than asking directly what matters to them.
What did you love doing that you have let go of?
Why ask it
Abandoned interests carry the story of a job change, a move, an illness, or a child. Hold it lightly, because it can go deeper than the tone of the question suggests.
When did you last surprise yourself?
Why ask it
Asks for evidence rather than self-assessment. A recent example suggests someone still taking risks, and a twenty-year-old example is its own kind of answer.
Is there a friendship that shaped you?
Why ask it
Friendship is less picked over than romance and often more formative. Expect a specific person and a specific period rather than a general statement, and expect it to open the conversation up.
What are you working on that you would be pleased to finish?
Why ask it
Current projects are easy to talk about and easy to follow up on weeks later, which is the mechanism that turns one conversation into a second one.
What is something you would want someone to know about you early?
Why ask it
Hands over the editorial choice. What people volunteer here, an illness, a child, a hard year, is usually what they think should shape how they are read.
What do you want the next few years to look like?
Why ask it
Ends looking forward rather than on an assessment of the past. Vague answers are common and fine; a specific one tells you exactly what someone is building towards.
Making it a conversation rather than an interview
Practical guidance for the conversation itself
How to actually use a list like this
Two or three questions is plenty
A whole evening needs perhaps three of these, spaced out and followed properly. Working through the list in order is the fastest way to make someone feel processed.
Follow up instead of moving on
The second question about the same answer is where the conversation actually happens. When did that start, what happened next, and who else was there will always beat a fresh topic.
Answer your own question first when it is a personal one
Going first sets the depth and gives them permission to match it. Asking what someone regrets while offering nothing yourself reads as an examination.
Match their depth, not your curiosity
If they give short answers to the light questions, the searching ones will not land yet. Wait for the moment when they volunteer something unprompted, then go one step further.
Keeping it comfortable
Let silences sit
Most of the better answers arrive two or three seconds after the point at which people rescue the pause. Count to three before you fill it.
Notice the questions they return
Someone who asks your version of a question back is engaged; someone who never does is either shy or finished. Both are worth reading accurately.
Take a no gracefully
If a question is met with a joke or a change of subject, that is an answer. Accept it visibly and do not circle back later in a different form.
What makes these fall flat
Front-loading the deep questions
Asking what someone regrets in the first ten minutes reads as intensity rather than interest. The searching questions work only once there is somewhere to put the answer.
Asking in order
It is obvious when there is a list, particularly on a date. Pick the two that suit the person in front of you and let the rest go.
Treating answers as data
Nodding while assessing is visible. If you find yourself scoring the answers rather than enjoying them, you are having an interview and so are they.
Only asking
Questions with nothing offered in return put the whole cost of the conversation on one person. Volunteer something of your own between each one.