Questions to Ask to Fall in Love
Questions to ask to fall in love, for two people on a date or a couple who want to feel closer. They are new questions built on the pattern of the well-known 36-question study: you both answer every one, take turns going first, and they get more personal as you go, from a short warm-up through three sets of twelve to a closing set. Each has a note on what a good answer sounds like and what to do with it, and what they create is closeness; whether it becomes love is up to the two of you.
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The questions
Each question, and why to ask it
Warm-Up
Who would you most like an hour alone with, anyone from any time, and what is the first thing you'd ask them?
Why ask it
The person matters less than the first question, so don't let either of you skip that half. A grandparent they never met tells you more than a celebrity does, though both are fair answers this early.
What does a close-to-perfect day look like for you, from waking up to falling asleep, and who is in it?
Why ask it
Listen for who is in the day and how full it is. A good answer has texture, such as a slow breakfast or a long drive, and it tells you how much company and how much quiet this person needs.
What do you sing when you're sure nobody is listening, and when did someone last catch you at it?
Why ask it
The car, the shower and the kitchen are the usual stages, and the song is often one they'd never admit to liking. Offer yours straight after. If either of you is willing to sing a line of it, the warm-up has done its job.
If one skill could simply be yours by tomorrow morning, no practice needed, which would you pick?
Why ask it
Ask what they'd do with it on the first day. Fluent Italian for a trip they keep postponing and a piano to play for a crowd are both good answers, and they point at very different wishes.
Would you take fame if it were offered, and what would you want it to be for?
Why ask it
Plenty of people say no and then describe a smaller kind of recognition they'd like, which is the real answer. Follow that thread and leave the red carpet alone.
What is the last thing that made you laugh until it hurt?
Why ask it
The last easy one before the sets begin, and a laugh is the right place to end the warm-up. If the story falls flat in the retelling, that's normal: 'you had to be there' still tells you who they were with.
Set One
What in your life right now are you most thankful for?
Why ask it
Short answers are fine here, but ask for the reason behind it. Someone who names a person will usually go on to describe them, and that's your first look at who matters to them.
Do you practice what you're going to say before a phone call or a hard conversation, and what was the last one you practiced for?
Why ask it
Rehearsers and improvisers tend to find each other funny, so say which you are. The last conversation they practiced for is usually a request or an apology, and it gives you a first look at what this person finds hard to say.
Can you tell me your life so far in three minutes: where it started, the turns it took, and where you are now?
Why ask it
Set a timer, because the limit is what makes it work: three minutes forces a choice about what counts. Notice which years get a sentence and which get skipped, and leave the gaps alone until a later set.
What did the people who raised you get right, and what would you do differently?
Why ask it
Putting 'get right' first keeps this from becoming a complaint session. An answer with credit and criticism both suggests someone who has thought about where they come from. All blame or all praise is worth noticing, without comment.
Who knew you best when you were a kid, and what did they see in you?
Why ask it
Often it's a grandparent, a teacher or a best friend's mother, and the answer comes with real warmth. If they say nobody did, don't rush to fix it. Say you're glad they told you and take your turn.
From what you've seen so far, where do you think the two of us are alike, and where are we clearly different?
Why ask it
The first question about the pair of you, placed this early so it can stay light. For a couple it's a chance to say something new, so rule out the answers you've both given before.
What are you proud of that would never go on a resume?
Why ask it
Good answers are small and specific: a friendship kept alive across years, a fear they got over, a kid brother taught to drive. Ask how long it took, and hold your own back until they've finished telling theirs.
Which quality matters most to you in a close friend, and which of your friends has it?
Why ask it
Naming a real friend keeps it from turning into a list of virtues. Remember the word they use: people sometimes hope for the same thing in a partner, and later on you can ask whether that's true for them.
Which memory do you go back to when you need cheering up?
Why ask it
Let them tell it slowly and ask one question about the senses, such as what the weather was or what they could hear. A treasured memory handed over this early is a small act of trust, so thank them for it plainly.
What have you been promising yourself you'll do for years, and what has kept it from happening?
Why ask it
The obstacle is the interesting part: money and time are honest answers, and 'I'm scared I'd be bad at it' is a braver one. Don't offer solutions yet. Advice has its own question in Set Three.
What were you like at sixteen, and what would that version of you make of your life now?
Why ask it
Usually funny first and then unexpectedly tender. A good answer is kind to the sixteen-year-old, bad haircut and all. If they're hard on who they were, don't argue the point. Ask what that kid was good at.
When you picture yourself at eighty, what do you hope you are still able to do every day?
Why ask it
It closes the set by turning toward the future, which is where the next one starts. Walking, reading and arguing with friends each show what a person thinks a life is for. If you're a couple, don't keep score of whether you appear in the picture.
Set Two
If you could know one true thing about your future, what would you ask, and would you really want the answer?
Why ask it
Whatever they'd ask about is often what they're least sure of right now: work, health, whether they'll find someone. Take the second half seriously, since some people decide they'd rather not know, and their reason is worth hearing.
How would you describe the weather in your family: warm, cool or stormy, and where do you stand in it?
Why ask it
The weather image lets people be honest without accusing anyone. Follow up by asking who they're closest to. If the forecast is stormy, listen and keep your opinions about relatives you've never met to yourself.
How was love shown in the house you grew up in: said out loud, done quietly, or left to be assumed?
Why ask it
Plenty of people either repeat what they grew up with or deliberately do the opposite, so ask which it is for them. Between two people getting closer, a mismatch here is useful to know about and nothing to worry over.
How can you tell, in yourself, that you're starting to care about someone?
Why ask it
Good answers are small tells: saving up things to tell the person, checking the phone more than usual, going quiet around them. On an early date, take it as information and don't ask whether any of it is happening now. A couple can each name the tell they spotted in the other at the start.
What fear do you carry that you rarely say out loud?
Why ask it
This is where the sequence turns, so slow down and let a silence sit. A good answer may be one sentence. The right response is 'thank you for telling me', then your own, with no reassurance that the fear is silly.
What is the hardest stretch you have come through, and what got you to the other side?
Why ask it
They choose how much to tell, and a headline with no details is a complete answer. Ask about what helped, not what happened. If it's clearly still raw, say so kindly and offer to come back to it another night.
What would you stop doing tomorrow if you knew your time was shorter than you assume?
Why ask it
'Stop' is easier to answer than 'start', and the answers are concrete: the commute, the grudge, the scrolling. A quick 'nothing, really' usually means the question hasn't been considered yet. Give it a minute before moving on.
What do you wish people understood about you without your having to explain it?
Why ask it
You are being handed the instructions, so listen as if you'll be tested on them. Say it back in your own words and ask whether you have it right, which matters more than any clever reply.
What last brought you to tears, and did you let anyone see?
Why ask it
A film or a song is a perfectly good answer, and so is last week. The second half carries more: someone who can name a person they cried in front of is telling you who they trust. Don't press anyone who says they can't remember.
What mistake of yours changed how you treat people?
Why ask it
A good answer owns the mistake plainly and spends more time on the change than on excuses. It takes nerve to tell, so don't ask for more detail than you're given, and don't hand out forgiveness that isn't yours to give.
When things go wrong for you, who do you call first, and what do you want from them?
Why ask it
Advice, distraction or simply a voice on the line: what they want from that call is how to be useful to this person on a bad day. It's reassuring when a name comes quickly. If they handle everything alone, ask gently whether that's by choice.
What are three things you have noticed and liked about me so far, as specific as you can make them?
Why ask it
Trade them one at a time, not three in a row, so it's an exchange and not a speech. Compliments on choices and character land better than ones on looks. Receive yours with 'thank you' and nothing else, which is harder than it sounds.
Set Three
What should someone know about you before they get close, the thing that is easier to hear early than to discover late?
Why ask it
Expect things like 'I go quiet when I'm upset' or 'I need a lot of time alone', which are gifts of information. The worrying version is a warning delivered as a boast, such as 'I'm a lot to handle', so ask what that looks like on an ordinary Tuesday.
What three things are true of both of us right now, each one starting with 'we'?
Why ask it
It sounds like a grammar exercise and works better than it should. 'We are both a little nervous' or 'we have both stopped checking the time' puts you on the same side of the table. Alternate, and keep every statement true.
What part of your life do you most wish you had company in?
Why ask it
Answers run from 'someone to cook for' to 'someone who understands my work', and each is a quiet description of what's missing. Don't volunteer for the role on the spot. Hearing it properly is enough for tonight.
Which embarrassing moment still makes you wince when it comes back to you at night?
Why ask it
Set Three needs a laugh by this point, and this is where it comes. Whoever is braver goes first. The one rule is that nobody says 'that's not so bad', because to the teller it is.
Where does your sense of humor stop: what do you never find funny?
Why ask it
A limit like this usually traces back to something lived through, and they may or may not say what. Take the line as given and remember it, since teasing is one of the first things to go wrong between two people getting close.
Who are you overdue to say something to, and what has kept you from saying it?
Why ask it
Thanks, an apology and 'I miss you' are the usual three. You're not there to make them pick up the phone. If they decide to on their own, ask later how it went.
What do you own that no amount of money could replace, and what is its story?
Why ask it
A breather with some weight to it: the object is usually worth almost nothing and stands for a person. Ask where it's kept. If it's within reach, on a wrist or in a wallet, ask to see it.
Who in your life could you least imagine being without, and do they know it?
Why ask it
Handle this one gently, and skip it if either of you has had a recent loss. For couples the honest answer may be each other, which is worth saying aloud even after years. On a date, it names someone you'd be meeting if this goes on.
What are you trying to work out at the moment, and would you like to hear how I would handle it?
Why ask it
Before giving any advice, say back how they seem to feel about the problem and check that you've read it right. That step tends to do more for closeness than the advice does. It has to be a real, current problem, not one that's already solved.
What did you assume about me at first that turned out to be wrong?
Why ask it
Good for a laugh and a little risky, so answer it kindly. For couples it's a road back to the beginning. On a date, 'I thought you'd be more guarded' is a compliment hiding inside a confession, and you can say so.
What part of you are you least sure someone could love?
Why ask it
The most exposed question on the page, and it's fine to agree to skip it on an early date. If it's answered, don't argue with the answer or hurry to disprove it. 'I'm glad you told me' is the whole reply, and then it's your turn.
What does being loved well look like to you, in ordinary everyday detail?
Why ask it
The set ends here because this turns everything before it into something practical. Look for small, checkable details, such as being asked about their day or having a hard week noticed. A vague 'being supported' deserves one follow-up: what did that look like the last time it happened?
Closing
What did I say tonight that you will still be thinking about tomorrow?
Why ask it
It tells the other person what landed, which they have no other way of knowing. If nothing comes to mind right away, wait. People tend to pick something small that the speaker has already forgotten saying.
Which question was hardest for you to answer, and what made it hard?
Why ask it
Talking about the difficulty is easier than the question was, and it sometimes produces the fuller answer that didn't come the first time. If they name one they skipped, that isn't an opening to ask it again.
What do you know about me now that you could not have guessed when we sat down?
Why ask it
For a new pair this is the evidence that the evening did something. For couples it's the real test: 'nothing new' means you've been summarizing instead of answering, so go back and redo one question as you are this year.
Is there an answer of yours you'd like to go back to and give again, more honestly?
Why ask it
There is usually one, often from Set Two, where it's tempting to play it safe. Make the second attempt easy by asking no follow-ups. It's a correction they're trusting you with, and it needs no discussion.
How do you feel right now compared with when we started?
Why ask it
Closer, tired, a bit exposed and oddly calm are all common, sometimes at once. Believe whatever is said, including 'I need some quiet'. If one of you feels more than the other, that's allowed, and tonight isn't the time to settle it.
What would you like the next conversation between us to be about?
Why ask it
It ends the evening by pointing past it, which is truer to how closeness grows than any big finish. A good answer is specific, like 'your brother' or 'that year abroad'. Remember it and bring it up within the week.
How to run the questions, and what they can and can't do
Practical guidance for the conversation itself
Before you start
Agree to it first
Both people should know what the evening is. Springing a closeness exercise on someone who thought it was only dinner is unfair to them and spoils the answers. Say what it is, say that either of you can skip any question, and ask whether they're in.
Pick the place and put the phones away
Choose somewhere you can hear each other and won't be hurried: a quiet corner table, a couch, a long walk. Keep one phone face down as a timer and the other out of sight. A glance at a screen in the middle of someone's answer to Set Two costs more than it would on an ordinary night.
How long to allow
The 36 questions come from a 1997 study led by the psychologist Arthur Aron, in which pairs of strangers had about fifteen minutes for each of three sets, forty-five minutes in all, and moved to the next set when the time was up. With the warm-up and the closing on this page, allow about ninety minutes: ten for the warm-up, twenty or so for each set, ten to close. With only an hour, do the warm-up and Sets One and Two and keep Set Three for another night.
Keep the order
The questions get more personal a little at a time, and that slope is the method. Skipping one is fine. Jumping ahead to Set Three is not, because the hard questions lean on the trust the easy ones built, and asked cold they feel like an interrogation.
How to take turns
Both of you answer every question
One of you reads the question aloud, then both answer before you move on. Nobody is the interviewer. The exercise works because the telling goes both ways at the same depth, so a question only one person answered is half done.
Alternate who goes first
Whoever reads the question lets the other answer first, then you swap for the next one. That way neither of you is always the one stepping out first on a hard question, and neither can wait to hear how far the other goes before deciding how honest to be.
Listen first, discuss later
A follow-up or two is good. Twenty minutes on question nine means you never reach Set Three. When an answer deserves a longer talk, say you'd like to come back to it and keep going. The Closing set asks what you want to talk about next for exactly this reason.
Match the depth you're given
If one person gives a real answer and the other gives a joke, the balance tips and the first one pulls back. Aim to go about as far as the other person just did, and a half step further when it's your turn to go first.
The pass rule
Either of you can pass on any question without giving a reason, and the other person is then free to pass too. A pass is not a failure, and it is never a cue to guess at what's behind it. If the passes pile up in one set, finish that set and stop there for tonight.
What these questions can and can't do
Not the study's own wording
The questions on this page were written for it. They keep the shape of the study's three sets of twelve, easy ones first, then harder ones about family, fear and bad times, then things said directly to each other, and they add a warm-up and a closing set the study did not have. If you want the researchers' original 36, they are in that 1997 paper, 'The Experimental Generation of Interpersonal Closeness'.
Closeness, not a spell
The study behind the 36 questions set out to make two strangers feel close in a single sitting, and closeness is what it measured, not love. Telling someone true things by degrees, and having them do the same while you both pay attention, tends to make people feel closer. Whether that grows into love depends on everything a list can't supply: attraction, timing, what you each want, and how you treat each other next week.
On an early date
Feeling close after ninety minutes of confiding is real, and it is a feeling about one evening. Enjoy it and make no promises on the strength of it. You still need to see how this person behaves when they're late, bored or disappointed. And never use the questions to hurry someone who is hesitant: closeness that one person was steered into doesn't hold.
For couples who know each other well
The risk is answering from memory, with the story you told five years ago. Agree to answer as you are this year, and to be surprised. Agree as well that nothing said during the questions gets brought out later in an argument. One answer used as ammunition is enough to make the next round guarded.
When to stop
Stop if either of you is upset beyond what the other can comfortably sit with, if one of you has gone quiet, or if it has started to feel like a test. Say 'let's leave it there', and do something ordinary together. The questions will keep. If an answer opens up something much heavier than an evening's talk can carry, it is kind to say so and to suggest it deserves someone trained to help.
The closing and the day after
The quiet minutes
The popular version of the exercise ends with a few minutes of looking at each other without speaking. It's optional, and both of you have to want to. If you try it, set a timer for two to four minutes and expect to laugh through the first one. On an early date the Closing questions do much the same job with less pressure.
Don't end on the heaviest answer
Set Three finishes on a practical question and the Closing set brings you back to the room on purpose. Afterward, do something that needs no talking about feelings: walk, order dessert, wash up side by side.
Keep what you were told
What the other person said belongs to them. Don't retell it to friends as a story about your date, and don't quote their hardest answer back to them by text the next morning. A short message that mentions something small and specific they said is the better follow-up.
Doing it again
A couple can come back to these once a year and find that the answers have moved. A new pair shouldn't repeat it the following week. After one evening like this, what builds closeness is ordinary time: errands, meals, an afternoon when nothing in particular gets said.