Questions to ask your best friend
The hard part of a long friendship is that you already know the facts, so these 40 questions skip the biography and go at what has changed — what they are carrying now, what they have stopped telling you, and what you have both quietly agreed not to mention.
Easy ones, to start
Nobody opens with the hard question. These are the ones you can ask with the plates still on the table, and they still tell you something.
- Who taught you something you still use every week?
- Who's been unexpectedly good to you this year, and what did they actually do?
- What's the best thing anyone here has ever talked you into?
- What's the last photo you took that wasn't of a screen, a receipt, or a parking space?
- What's your most-used app that you're not proud of?
- What's something everyone else seems to love that you've quietly given up on?
- What's been on repeat in your headphones lately, and what does it do for you?
- If I had one free day in your city, where would you send me first?
- What's the last thing you got weirdly obsessed with?
- What's the last thing that made you laugh until you couldn't speak?
Questions that actually go somewhere
The middle rung. Still safe, but the answer is about who someone is rather than what they did, which is the whole difference.
- When did you last cry, and what set it off?
- What's the part of your life you're most afraid other people find boring?
- What's a decision from the last couple of years you're still not sure you got right?
- What are you telling people you're fine about that you're not actually fine about?
- What's the hardest thing in your life right now that you don't usually bring up?
- What's the loneliest part of your week?
- What do people consistently get wrong about you?
- What do you do when things get hard that you wouldn't want filmed?
- Which friendship of yours has quietly ended, and do you know why?
- What's something you want more of and haven't asked anyone for?
- Where have you felt most like yourself in the last few months?
- What are you doing right now mostly because someone expects you to?
- When did you last change your mind about something that actually mattered?
- Which version of yourself do you miss?
The ones most people never get to
Ask these when there is time and nobody has to be anywhere.
- Tell me what you actually like about me — including the part you'd normally leave out.
- If this friendship faded out, what would you miss that you've never said out loud?
- What do you envy about my life? Be honest.
- What do you think I'm avoiding?
- What's something you'd be relieved to say out loud right now if you knew nobody would flinch?
- What's going on in your life right now that I'd have to ask about three times before you'd really tell me?
- What's the thing from the last few years you're most ashamed of? One sentence is enough.
- What do you think I've got wrong about you?
When something is off
The ones people skip. Skipping them is usually why the same thing keeps coming back.
- What's changed about you since we met that I probably haven't noticed?
- Who did you used to be close to that you'd message today if you weren't embarrassed about the gap?
- What have I done, or not done, that made it harder to stay close?
- When have you needed me and not told me?
Where things are going
Fewer of these on purpose. A conversation that is only about the future is a planning meeting.
- You get a completely empty week, no obligations. What's the first thing you actually do?
- What are you noticeably better at than you were a year ago?
- What do you do on a Saturday morning now that the you of five years ago wouldn't recognise?
- What's an ambition you've quietly let go of?
Some questions are easier to answer when neither of you chose them.
Turn one over. You would not have picked it — that is the point.
Six questions from this page, face down.
On the site they live on a wheel. You spin, it lands, nobody chose it.
Does any of this actually work?
Time is the usual answer and it is not quite right. Two studies — 355 adults who had recently relocated, and 112 first-year students tracked three times over nine weeks — found hours spent together predicted closeness, but not on their own: time in leisure activities predicted closeness specifically, and two particular kinds of everyday talk predicted the change in closeness between waves. Hours are the container. What you do in them is the mechanism, which is the part a long friendship stops doing.
The second thing worth knowing is that you are probably wrong about how this is landing. After conversations, people systematically underestimated how much their partner had liked them and enjoyed their company — an effect measured in strangers in the lab, in members of the public at a workshop, and, most relevantly here, in first-year students getting to know their dorm mates, where it persisted for several months as the relationships developed. Being unsure whether a deeper question was welcome is the normal state, not a signal.
Hall (2019), How many hours does it take to make a friend?, Journal of Social and Personal Relationships · source
Boothby, Cooney, Sandstrom & Clark (2018), The Liking Gap in Conversations: Do People Like Us More Than We Think?, Psychological Science · source
Some of these will land as an interrogation if the friendship has gone sideways, and a friend who has been avoiding you will hear the deep ones as an accusation. If something is actually wrong, say the thing; do not route it through a question.
Last checked 28 August 2026.