Questions to Ask Your Best Friend
For the one friend who already knows most of your answers. The list opens with Know me questions, where your best friend guesses things about you and you find out how close they get, then moves through shared memories, funny, deep and future. Each tag runs from easy to harder, and every question comes with a note on what to listen for.
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The questions
Each question, and why to ask it
Know me
What do I always end up ordering when we can't decide where to eat?
Why ask it
A gentle first test that a best friend should pass. If they get it wrong, find out whether your tastes changed or they just weren't paying attention.
What phrase do I overuse without noticing?
Why ask it
They will answer instantly and probably in your voice. You may not enjoy learning it, but you'll hear yourself say it within the hour.
What song would I put on first if you handed me the speaker?
Why ask it
Tests whether they know your current taste or the one you had when you met. Either answer is a small portrait of how they picture you.
Which of my stories have you heard the most times?
Why ask it
Everyone has a story on heavy rotation, and only a best friend has kept count. Ask them to tell it back to you and see which details they've added.
What is the fastest way to annoy me?
Why ask it
They know, and they have probably used it on purpose. Compare their answer with what you'd have said, since the gap is how you come across versus how you feel.
What chore will I put off until it becomes an emergency?
Why ask it
Best friends see the unglamorous logistics of your life. A correct answer here is proof of real proximity, not just affection.
What would I do with a surprise free afternoon and no one to answer to?
Why ask it
Find out whether they describe what you'd actually do or what you claim you'd do. The honest version is usually less impressive and more accurate.
What am I like when I'm hungry or tired, and how early can you spot it?
Why ask it
Close friends read your warning signs before you do. Ask what the first sign is, because you can use that information on yourself.
What is my tell when I'm pretending to like something?
Why ask it
Your polite face has fooled fewer people than you think, and your best friend least of all. Expect a demonstration.
What topic can I not stop talking about once I get started?
Why ask it
A kind way of asking what you're boring about. The good news is that they've listened anyway, which is more or less the definition of the job.
What am I most likely doing when I haven't texted back all day?
Why ask it
Their guess shows what story they tell themselves about your silence: busy, asleep, overwhelmed or ignoring them. Worth correcting if it's the last one.
What do I do when I'm nervous that I probably don't know I do?
Why ask it
A chance to learn something about yourself that is visible to everyone else. Ask this only if you truly want to know, since you can't un-know it.
What do I think I'm good at that I'm honestly not?
Why ask it
Requires a friendship that can take a hit. Promise in advance not to argue, and notice how long they hesitate: a short pause means they've had the answer ready for years.
When I'm upset, do I want advice, distraction or just company?
Why ask it
If they get this right, tell them, because they've been doing careful work you may never have acknowledged. If they get it wrong, you've just saved each other years of misfires.
What compliment would I never believe, even coming from you?
Why ask it
Shows whether they've noticed where your confidence runs out. They may then deliver the compliment anyway, and you should let them.
Which decision of mine did you understand before I had explained it?
Why ask it
Being understood without explanation is about the rarest thing a friendship offers. Naming a time it happened tells you what they see clearly in you.
What do you think I worry about most but rarely say out loud?
Why ask it
A guess from someone who has watched you for years is often closer than your own account. If they're right, say so, and if they're wrong, tell them the real one.
What do you think my biggest blind spot is?
Why ask it
The hardest of the Know me questions, so save it for last and mean it. Thank them for the answer before you respond to it, and don't ask unless you can do that.
Memories
What's the first memory of me that comes to mind, without thinking about it?
Why ask it
Speed matters here: the unfiltered answer is often a tiny, odd moment, not a milestone. Those small ones show what you look like in their head.
What's the worst plan we ever actually went through with?
Why ask it
Every close friendship has a caper that should have been vetoed. Deciding whose idea it was may take the rest of the evening.
What day out, drive or trip with me would you repeat exactly as it happened?
Why ask it
The word 'exactly' includes the rain, the wrong turn and the bad sandwich. If they'd keep the flaws, you've found one of the friendship's load-bearing memories.
Which photo of us best shows what our friendship is actually like?
Why ask it
Rarely the nice posed one. Have them find it if they can, and explain what it shows that the good photos miss.
What song will always make you think of me, and what were we doing?
Why ask it
Music pins a friendship to a time and place: a car, a kitchen, a terrible school dance. You may learn that you've been part of someone's soundtrack without knowing it.
What's the most trouble we ever got into together?
Why ask it
Shared guilt is a strong glue. The retelling usually reveals that each of you remembers the other as the instigator.
What moment from our friendship have you retold to other people the most?
Why ask it
The story they tell about you when you aren't there is the public version of the friendship. It may not be the one you'd have chosen, which is the interesting part.
What did we once fight about that seems ridiculous now?
Why ask it
Laughing at an old argument is a way of confirming it's fully healed. If one of you isn't laughing, that is worth knowing too.
Which phase of mine took the most patience from you?
Why ask it
The all-consuming hobby, the terrible relationship, the year of talking about one thing. A friend who stayed through it has earned the right to describe it.
When did you realize we were going to be close, not just friendly?
Why ask it
There is usually a turning point, often a moment when one of you was unguarded. The two of you may name different days, and both are true.
What was going on in your life when we met that I didn't know about at the time?
Why ask it
You met a person in the middle of their own story. This fills in the background, and it sometimes explains why the friendship mattered so quickly.
When did I surprise you by doing something you didn't think I had in me?
Why ask it
Asks them to recall the moment their picture of you had to be updated. It's a compliment with a small insult folded inside, which suits a best friend.
What have I said to you that you've never forgotten?
Why ask it
Be prepared for it to be something you have no memory of saying. Offhand remarks carry further than planned ones, for good and for ill.
What's the longest we've gone without talking, and what was it like to pick back up?
Why ask it
A friendship that survives a gap earns a particular confidence. If the gap still feels unexplained to one of you, this opens the door gently.
When were you worried about me and didn't say so?
Why ask it
Friends often watch a rough patch in silence, unsure whether to step in. Hearing about it later shows you how you hide things, and gives them permission to speak up next time.
When did we come closest to drifting apart, and what pulled us back?
Why ask it
Only for friendships with some years behind them. Naming the near miss, and what saved it, is how you learn what to do when the next one comes.
Funny
If the two of us had a reality show, what would it be called?
Why ask it
The title will sum up how they see the pair of you in three or four words. Follow up by asking what the recurring segment would be.
What's the worst gift I have ever given you, and did you keep it?
Why ask it
Enough time has passed for honesty. If they still have it somewhere, that says more about the friendship than the gift does.
What's the worst movie or show I've ever made you sit through?
Why ask it
They remember, and they've been waiting. Accept the verdict with grace, because you almost certainly have one of theirs saved up in return.
What food opinion of mine have you been tolerating in silence?
Why ask it
Low risk, high indignation. It's a useful warm-up for harder honesty later, since you both practice disagreeing about something that doesn't matter.
What's the funniest message I've ever sent you, on purpose or by accident?
Why ask it
Many best friends keep an archive. The accidental ones, the typos and wrong-chat disasters, are usually the winners.
What is my worst fashion era, and do you have photographic evidence?
Why ask it
A best friend is the keeper of the records. Negotiate a mutual disarmament treaty before anyone opens their camera roll.
Which of us is the bad influence, honestly?
Why ask it
Both of you will point at the other, and both will have evidence. Best settled by listing incidents, which is where the stories come out.
What would our joint business be, and how quickly would it fail?
Why ask it
The business idea shows what you think you're good at together, and the cause of failure shows what you know about each other's weaknesses. Both are said with love.
If we swapped lives for a day, what's the first thing you'd get wrong?
Why ask it
Reveals what they think is hardest or strangest about your daily routine. You may discover they have no idea what you do for most of the day.
Which of us would last longer on a silent retreat, and how would the other get sent home?
Why ask it
A comparison where losing is as flattering as winning. The method of getting sent home is where the accuracy lies.
What impression of me do you do when I'm not around?
Why ask it
They have one. Seeing it is unsettling for a second and then very funny, and it shows which of your mannerisms are loudest to other people.
What is my most chaotic trait, and when did you first witness it?
Why ask it
The origin story matters: there was a day they first saw it and chose to stay. Works best with a friend who has real material and enjoys telling it.
If you had to introduce me to a stranger using only my three worst habits, which would you pick?
Why ask it
Limiting it to three forces a ranking, and the ranking is the joke. Ask only if you can hear 'always late' without launching a defense.
What private nickname do you have for me that you've never said to my face?
Why ask it
It may be what you're saved as in their phone, or something their family calls you. Occasionally the answer is nothing, which is its own kind of funny.
What would my villain origin story be?
Why ask it
Whatever they name is the small injustice they know you'd never get over: a stolen parking space, a misquoted fact. It shows how well they know your grudges.
If you gave a toast about me that had to include one embarrassing story, which story would it be?
Why ask it
Valuable intelligence if a wedding or milestone birthday is ever on the horizon. It also tells you which embarrassing story they consider affectionate and which is off limits.
What's the most embarrassing thing you've seen me do that I think nobody noticed?
Why ask it
Proceed knowing that you cannot take the answer back. A true best friend has been sitting on at least one of these out of mercy.
What do I do that would be a dealbreaker if I weren't already your best friend?
Why ask it
Everyone grandfathers in a few flaws for the people they love. Hearing yours is humbling, and a reminder that being tolerated is an underrated part of being known.
Deep
What do you get from this friendship that you don't get anywhere else?
Why ask it
A warm way into the deeper questions, since the answer is almost always good news. It also tells you what to keep doing, which you may have been doing by accident.
What are you proud of me for that I've never heard you say?
Why ask it
Friends assume this goes without saying, so it goes unsaid for years. Have your own answer ready, because they will turn it around on you.
What do you think has kept us close when other friendships faded?
Why ask it
Makes you both name the mechanism, whether it's honesty, habit, humor or stubbornness. Once you know what it is, you can do it on purpose.
What do you think I'm too hard on myself about?
Why ask it
Your best friend has watched you hold yourself to rules you'd never apply to them. Their answer tends to be right, and it's easier to hear from them than from yourself.
What do you rely on me for that you'd have trouble replacing?
Why ask it
People seldom say out loud what job a friend does in their life. The answer might be practical or might be 'you're the only one who remembers my dad', so leave room for either.
What do you admire in me that you'd like more of in yourself?
Why ask it
Answer it about them straight afterward, so it doesn't turn into fishing for praise. Long friendships often run on a trade, each person supplying what the other is short on.
How have I changed since we met, for better and for worse?
Why ask it
Few people have the data to answer this, and your best friend is one of them. The 'for worse' half is the reason to ask, so don't let them skip it.
What did you believe about yourself when we met that you no longer believe?
Why ask it
Turns the lens onto them, which a good conversation should do regularly. You were a witness to the change, so add what you saw from the outside.
Where do you think I sell myself short?
Why ask it
Different from asking about strengths: it asks where they've watched you step back from something you could have had. Expect a specific incident you hoped they'd forgotten.
What part of your life do you feel I understand the least?
Why ask it
Even best friends have zones they've never really entered, such as the other's work, faith, family or marriage. The answer is an invitation, so follow it with 'tell me about it'.
Have you ever been jealous of me, and what was it about?
Why ask it
Envy between close friends is ordinary and almost never discussed. Saying it aloud usually shrinks it, and you may find the feeling ran in both directions.
When you're struggling, what makes it hard to tell me?
Why ask it
It assumes there is something, which is more honest than asking whether there is. The obstacle might be your reaction, their pride or plain bad timing, and only one of those is yours to fix.
What are we like for each other at our worst?
Why ask it
Every pair has a failure mode: enabling, competing, complaining in circles. Naming it together, as a shared habit and not an accusation, is how you catch it next time.
When have I hurt your feelings without realizing it?
Why ask it
Ask only when you can hear the answer without explaining yourself. The incident is often small and old, and what they want is for it to be known, not relitigated.
What boundary have you wanted to set with me but haven't?
Why ask it
Close friendships accumulate unspoken resentments about time, favors and late-night calls. Hearing one now is far cheaper than discovering it later as distance.
What do you think I need to hear that you haven't wanted to say?
Why ask it
The friendship has to be sturdy for this one. You are handing over a license, so honor it: no rebuttal on the day, and a genuine thank-you.
Is there anything you've been afraid would change how I see you?
Why ask it
Offer it as an open door and nothing more. If the answer is no or not yet, accept it at once, because the asking alone tells them the door exists.
What's something you've never told me because the timing was never right?
Why ask it
Here the question itself creates the right time. Ask it somewhere private with no deadline, and be ready for anything from a confession to a long-delayed compliment.
Future
What are you looking forward to right now, large or small?
Why ask it
The easiest way to start talking about the future. If they struggle to name anything, that is worth noticing, and worth planning something together to fix.
What trip do we need to take while we can still do it badly?
Why ask it
The phrase 'do it badly' gives permission for cheap, underplanned and slightly uncomfortable, which are the trips people remember. Get as far as picking a month.
What tradition should we start this year and keep for decades?
Why ask it
It helps a long friendship to have something fixed in the calendar. Keep it small enough to survive babies, moves and bad years: one breakfast, one hike, one phone call.
What do you want to learn in the next few years that I could learn alongside you?
Why ask it
A shared project gives an old friendship new material. Even if you never sign up for the class, you'll find out what they're currently curious about.
What will the two of us be like as old people?
Why ask it
Usually played for laughs, with matching chairs and loud opinions. Underneath is an assumption worth hearing: that you will both still be there.
What skill or habit do you hope to have built by this time next year?
Why ask it
A one-year horizon is close enough to be real. Ask whether they want you to check in on it or stay out of it, since friends differ sharply on that.
What's one thing you hope I finally do in the next year?
Why ask it
They have watched you circle something for a long time. The word 'finally' lets them say so, and their answer is often the push you were waiting for.
What goal of yours could I actually help with, and how?
Why ask it
Moves support from the general to the specific. The help they ask for is usually modest: read a draft, make an introduction, come along the first time.
If we could plan one perfect reunion day every year, what would be on the schedule?
Why ask it
Most useful for friends who live apart or are about to. The schedule shows what they value about time with you: the talking, the doing or the doing nothing.
What do you hope we are still laughing about in thirty years?
Why ask it
Asks which current chapter will become legend. It's a sideways way of saying that the present, even the irritating parts, is worth remembering.
When life gets busier, what's the minimum contact that would still feel like us?
Why ask it
Practical and unusually kind. Agreeing on a floor, a weekly voice note or a monthly call, stops a busy season from feeling like a rejection.
If one of us moves far away, what do we do to stay close?
Why ask it
Easier to plan before it happens than to improvise after. Be concrete about visits and calls, because good intentions alone tend not to survive a time difference.
How do you want me to tell you when I think you're making a mistake?
Why ask it
Get the instructions now, while no mistake is on the table. Some people want it straight and once, others want questions, and using the wrong method wastes the warning.
What role do you want me to play in the big moments ahead of you?
Why ask it
Weddings, moves, births, funerals, launches. People have quiet hopes about who stands where, and it is far better to learn them early than to guess.
What change in either of our lives are you most nervous about, for the friendship's sake?
Why ask it
A new partner, a baby, a job in another city. Saying the worry out loud lets you both plan around it, instead of each pretending not to see it coming.
What do you want your life to look like in five years that you haven't said out loud yet?
Why ask it
For a half-formed plan, a best friend is often the safest first audience. Respond with curiosity, not logistics, or the plan goes back into hiding.
What dream would you want me to hold you to if you started backing out?
Why ask it
This gets their consent in advance to be pushed. Ask them what backing out would sound like, so you can recognize the excuses when they come.
What version of your future have you quietly let go of?
Why ask it
The heaviest question in this tag, since it involves a small grief. There's no need to fix it or argue them back into it, and saying it to someone is often enough.
What do you want to be true about our friendship when we're eighty?
Why ask it
Made to be asked last. The answer works as a mission statement, and it is worth each of you writing down what the other one says.
How to ask your best friend
Practical guidance for the conversation itself
Before you start
Say why you are asking
A best friend will notice a sudden run of big questions and wonder what is wrong. Tell them the truth: you found a list and realized there are things you have never asked. It removes the suspicion and turns it into a shared project.
Trade, do not interrogate
Every question goes both ways. After they answer, answer it yourself, and for the Know me questions, let them quiz you back. A one-way session turns a friend into a subject.
Choose side by side over face to face
Walking, driving, cooking or doing a puzzle all make hard questions easier, because nobody has to hold eye contact while they think. Keep the sitting-across-a-table version for the light tags.
Decide what you will do with a hard answer
Some of the Deep questions invite criticism of you. Before asking one, decide that your only job is to listen and say thank you. If you know you will argue the point, leave that question for another day.
Ways to use the list
The Know me quiz
- 1Each of you picks five Know me questions without showing the other.
- 2Take turns asking. The other person guesses, then you give the real answer.
- 3Do not keep score.
- 4For every wrong guess, ask what made them think that. The wrong guesses are the useful part.
One a week by message
- 1Agree on a day of the week.
- 2Take turns sending one question from Memories or Future as a text or voice note.
- 3Answer within the week, at whatever length you like.
- 4Keep the Deep questions for calls and visits.
The long-distance call
If you live apart, calls tend to become status reports: work, family, weather. Open with one question from the list before the catching up starts. It changes what the rest of the call is about.
The annual check-in
- 1Pick a date that already means something, such as a birthday or the anniversary of when you met.
- 2Each choose two Future questions and one Deep one.
- 3Ask them over a meal.
- 4Write down one thing each of you said you wanted, and read it back the following year.
Handling the hard parts
When a guess about you is wrong and it stings
Finding out that your best friend misreads something about you can feel like a small betrayal. It is not. It is information you could not have gotten any other way. Correct it kindly and ask what gave them that impression.
When they tell you something you did hurt
Do not defend, explain or apologize at length in the moment. Say you are glad they told you, ask if there is more, and come back to it a day later once you have thought about it. The second conversation is where the repair happens.
When the answer is a joke
Humor is how many close friends dodge. Laugh, because it is probably funny, then say 'and the real answer?' once. If they joke again, let it go. They heard the question, and it may come back up on its own.
When you find a gap
Long friendships run on old information. If a question reveals that you are out of date on something big in their life, do not apologize for it, ask about it. Catching up is the whole reason to do this.