Questions to ask your crush to actually know them.
To know them better is curiosity practice, not interview. The goal is to surface the version of them you would not see in passing. Once mutual engagement is clear, the prompts can go deeper; the page below is for the broad cross-channel get-to-know moment.
Five sections, organised by category of intent: what makes them light up, how they think about people, what they do when nobody is watching, the version of themselves they are working on, and a small set of lighter prompts. Read deep questions when this section is too gentle, and reading their interest for the signal layer.
What makes them light up
Listen for energy in the answer, not content. The prompts in this section are designed to find the thing they will talk about for ten minutes without realising it.
What is something you can talk about for an hour without realising the time has passed?
Their absorbing topic. Reliable signal of where their attention naturally goes.
What is a project you would happily work on for free, just to be involved?
Free-and-just-to-be-involved is the test of real interest.
What is the thing in your life that you keep being pulled back to, even when you try other things?
Pulled-back-to is more honest than passion. Listen for the gravitational answer.
What is the kind of weekend where you go to bed pleased with the day you had?
Their version of a good day, in their words.
What is a small thing that has happened to you this week that you keep thinking about?
Small-and-keep-thinking-about reliably surfaces a real noticing.
What is a recent moment when you felt fully yourself?
Tells you when they feel most themselves. Listen for the conditions, not just the moment.
What is the kind of conversation that always leaves you better than it found you?
Reveals what they want from talking with people.
What is the most you have laughed in the last year, and what was it about?
Specific-laughter-prompt. Tells you who they laugh with.
How they think about people
Relational intelligence, not the gossip version. These ask how they navigate the people in their life, which is a strong signal of how they will navigate you.
Who is the friend you have known the longest, and what do they know about you that is hard to fake?
A long friendship is one of the cleanest character signals.
What is a friendship of yours that has changed shape recently?
How they handle change in a friendship is how they will handle change with you.
Who is the person in your life you most want to be a little more like?
Their model. Often more revealing than their goals.
What is something you have learned about yourself from a recent conflict?
Conflict-as-mirror prompt. Listen for self-awareness.
Who is the friend you call when you have actually good news, before you call anyone else?
First-call-friend tells you about their inner circle.
What is the kind of thing your closest friends rely on you for?
How they show up for the people they love is how they will show up for you.
What they do when nobody is watching
Identity, not ambition. The questions about who they are when there is no audience tend to be more revealing than the questions about what they want to be.
What is a small habit you have that you actually like about yourself?
Stops them defaulting to self-deprecation. Lets them name a private good thing.
What is something you do on weekends that you would not put on social media?
The unposted weekend is closer to the truth.
What is the kind of evening you would happily have on your own?
Their solitude practice tells you a lot about their tolerance for the inside of their own head.
What is the most absorbed you have been in something recently, where you forgot the time?
Their flow state. Listen for whether they have one.
What is a thing you do for yourself that you would feel slightly silly explaining to a stranger?
The slightly-silly explains itself. Specific, gentle, telling.
What is the version of yourself that comes out only with people you really trust?
Asks them to imagine who they are with their guard down.
What is a small kindness you do for yourself that you keep up with?
Listen for whether they have a self-kindness practice they can name.
The version of themselves they are working on
Gently future-tense. These are not job-interview answers. They ask about the changes they are quietly making, which is a softer prompt than the goals they are pursuing.
What is something you are working on quietly that you are not really telling anyone about?
Quietly is the keyword. Stops it being a polished answer.
What is a habit you have started in the last year that you actually want to keep?
Started-and-want-to-keep prompts a real answer rather than a wish.
What is the thing about yourself you have come to be more patient with?
Self-patience, as a developmental marker.
What is something you used to think you needed, that you have learned you do not?
Subtraction-as-growth. A more interesting prompt than addition.
What is a part of your life that has changed direction in a way you are pleased about?
Change-and-pleased is a calmer way to ask about growth.
What is something you can do now that you could not do five years ago, that no one would notice?
The invisible competence. Often the one they are most proud of.
Lighter prompts, deliberately few
This is not a fun-questions dump. Three lighter prompts, used as ballast between the heavier ones above.
What is the most pleased you have been with a small purchase recently?
Small-and-pleased reveals taste, not income.
What is the kind of weather that always makes you feel slightly more like yourself?
A small, sense-rooted question. Reliably easy to answer.
What is the most consistent compliment you get, that you have stopped noticing?
Stopped-noticing is the gentle reframe.
On the thirty-six questions framework: the original Aron et al. (1997) study designed a structured strangers-meeting exercise where two people agreed to participate. Some of the prompts on this page draw on that spirit, but the thirty-six are not a one-sided text-thread tool, and not all of them belong in a crush conversation. Five of the original set, with attribution: Given the choice of anyone in the world, whom would you want as a dinner guest?; Would you like to be famous? In what way?; Before making a telephone call, do you ever rehearse what you are going to say?; What would constitute a perfect day for you?; When did you last sing to yourself? To someone else? Read the whole exercise at the Greater Good in Action project at ggia.berkeley.edu/practice/36_questions_for_increasing_closeness.
The app has two hundred more for this stage, plus shuffle, save, and ladder mode, the ten-prompt sequence paced for ten conversations.
It is not built yet. The cluster app ships later this year. Read more about ladder mode on the how to use these prompts page.