Questions to ask your crush over text, paced for the thread you are actually in.
Text gives you reaction time. The recipient has time to write a real reply. The wrong text prompt invites a one-word answer that kills the thread; the right one invites a two or three sentence reply that gives you something to follow up on.
The prompts below are organised in four sub-sections: opening the thread, mid-thread, story-inviting, and lightly flirty. Use one per message; do not stack three in a row; let the silence between messages be part of the conversation. Read the how to use these prompts page for the technique notes.
Snapchat and Instagram DM use the same prompts with slight pacing tweaks: Snapchat is more ephemeral, so quick-reaction prompts land best; Instagram DM is more deliberate, similar to text. Whichever channel, one prompt per message is still the rule.
Opening the thread
These are for the first five or ten messages, when you have just started a thread or you have not messaged in a while. The goal is to invite a real reply, not a polite one. Keep them light, but specific.
What is the weirdest thing you have done this week, and was it a good kind of weird?
Lighter than asking how their week was. Asks them to volunteer something they noticed about themselves.
What were you in the middle of when you saw this message?
A small invitation to tell you about their day, with a built-in escape if they want to keep it short.
What is the playlist you would never put on a shared speaker?
Asks for something they are slightly embarrassed by, in a way that is fun, not exposing.
What is something small you have been pleased with this week?
Pleased is a deliberately gentle word. Listen for whether they can name one.
What is the last thing that genuinely made you laugh out loud at your phone?
A specific frame for a question that is usually too vague.
What is your favourite kind of weather, and where would you want to be in it?
Two-part questions work over text, they invite a longer reply.
What is one thing you have planned for the next few weeks that you are quietly looking forward to?
Quietly is the keyword. Not the big plans, the small ones they are private about.
Mid-thread, once it has settled
By message twenty or so, the thread has its own rhythm. These are for that point: questions that earn a fuller reply because the conversation has earned it.
What is something you used to be really into that you have grown out of?
Tells you what they have the self-awareness to outgrow. Not a callout, an invitation.
What is the last thing you bought for yourself that felt slightly indulgent?
A small window into how they treat themselves.
Who is the friend you call when you have actually good news, before you call anyone else?
Asks about their inner circle without asking them to list their friends.
What is a film or a book that has stayed with you longer than you expected it to?
Stayed-with-you is more revealing than top-five.
What is the kind of evening where you go to bed pleased with the day you just had?
Their idea of a good day, in their words. Better than asking what they do for fun.
What is something you do that always puts you in a slightly better mood?
Their self-regulation toolkit, in one answer.
What is a place near you that you go to when you want to think?
Reveals whether they have a thinking practice and where it lives.
What is the small habit you have that you actually like about yourself?
Self-knowledge without performance. Listen for whether they can name one.
Story-inviting prompts
These are the ones designed to earn a longer reply. The point of asking a story prompt over text is that they have time to remember and write a real answer. Use these once the thread is breathing.
What is the best meal you have had in the last year, and what made it that meal?
Specific, embodied, easy to answer at length.
What is a trip you took that did not go to plan but turned out better for it?
Asks for a story with a turn in it. Almost everyone has one.
What is a friendship you have that started in a strange way?
Reveals how they meet people, how they invest in friendships, and a story all at once.
What is something you learned later than you should have, and what changed when you did?
Vulnerability without trauma dump. The turn is the interesting part.
What is the most you have laughed in a single conversation in the last year, and what was it about?
Not the biggest event, the funniest one. Tells you who they laugh with.
What is a job or a side project you have had that taught you something unexpected?
Listen for whether they can name what they learned, not just what they did.
What is the longest you have ever spent properly absorbed in something, and what was it?
How they spend their attention is more telling than how they spend their money.
What is a piece of advice you got from someone you barely knew that turned out to matter?
A surprisingly common kind of story. Watch for whether they remember the person specifically.
Lightly flirty, paced for text
Flirty over text is harder than flirty in person, because the recipient cannot read your tone. The trick is to be specific and a little playful, never crude. These lean in slightly without leaning over.
What is the most underrated compliment someone has given you?
A flirty prompt by the back door. Listen for what they consider a compliment, not just who gave it.
If I told you I had been thinking about something you said earlier, would you guess right which thing it was?
A gentle lean-in. Says you remember without saying it directly.
What is a tiny detail about someone that has made you stop and notice them?
Asks them to talk about how they look at people. Useful intel.
What is the thing about you that the people who really know you would say first?
Reframes flattery as curiosity. Lets them brag a bit, gently.
What is the most you have ever liked someone before they knew about it?
A direct prompt. Use only when the thread is established.
What would I be surprised to learn you are good at?
Asks them to flatter themselves a little, on your invitation. Only after the thread is warm.
What is the kind of message that always makes your day better when you get one?
Tells you what to send them, with no pressure. A small gift in question form.
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.