The early thread: questions for the first few messages with your crush.
The first five or ten messages are calibration. The wrong icebreaker is a generic prompt that signals you have not been paying attention to who they are. The right icebreaker is specific to them, light enough to invite a casual reply, and structured to give them something easy to respond to.
The prompts below are organised by message position: ten specific-to-them openers, ten low-stakes follow-ups for messages three to five, and five story-inviting prompts for once the thread has settled into a rhythm. Read how to use these prompts for the technique notes.
Specific-to-them openers
The first message of a thread does most of the work. The wrong opener is generic ("hey", "what's up") and signals nothing. The right opener references something specific to them, light enough to invite a casual reply.
I just saw the thing about [the band / the trip / the project] you mentioned, did it actually happen?
Reference-and-follow-up. Says you remembered without making it a thing.
Was the [event / class / weekend] as good as you thought it would be?
Lets them tell you about a recent thing on their own terms.
What was the verdict on [the place / the book / the film] in the end?
Gives them a structured way to share an opinion, low-stakes.
Did the [thing they posted / mentioned] actually go to plan?
Asks them to update you on something they are already thinking about.
I keep thinking about something you said about [topic], can I ask you a follow-up?
Sets up the next message and signals that you have been paying attention.
What is the funniest thing that has happened to you since we last spoke?
Light, specific to them, and assumes there is one. Almost always there is.
What is a small thing about your day that you would tell a friend about later?
Casual, low effort to answer, surfaces something specific.
What is the most pleased you have been with yourself this week?
Pleased is a deliberately soft word. Stops them deflecting into modesty.
Who in your life would have made the same choice you made about [thing they mentioned]?
Curiosity about how they decide things, dressed as a follow-up.
What is a place near you that you have been meaning to go and have not yet?
Sets up future plans without making it a plan.
Low-stakes follow-ups for messages 3-5
Once the icebreaker has landed, the next few messages are about whether the thread can find a rhythm. Keep them light, specific, and easy to answer. Any of these can be the second thing you send.
What was the unexpected thing about it?
A universal follow-up that earns a real answer.
Who else thought it was as good as you did?
Asks about their people. Tells you who is in their orbit.
What were you doing right before you went?
Practical, easy, surfaces a story without asking for one.
What would have made it slightly better?
A discerning question. Lets them be honest without complaining.
What is the thing you keep thinking about from it?
Kept-thinking-about is more revealing than what-was-the-best-bit.
Were you the one who suggested it, or were you persuaded?
Tells you whether they lead or follow in their friendship group.
What was the smallest thing that made it for you?
Smallest is the discipline. Forces specificity.
What is the next thing in that direction you would like to do?
Sets up future plans naturally, without committing either of you to anything.
Who would you go with again?
Reveals the inner circle without asking who their friends are.
Would it have been better if the weather had been different?
A neutral, specific follow-up that often gets a long answer for no reason.
Inviting a longer story
By message six or eight, you can ask something that earns a longer reply. The thread has shown it can carry weight. These prompts invite a story without forcing one.
What is a friendship of yours that started in a strange way?
Almost everyone has one. The story tells you a lot about how they meet people.
What is the most you have ever changed your mind about something?
Asks for a story with a turn. Listen for whether they can name the thing that changed it.
What is a piece of advice you got from someone you barely knew that has actually mattered?
Tells you who they listen to, and how easily.
What is a project or job you had that taught you something unexpected?
Story-shaped, easy to answer, and surfaces what they value about their work.
What is the longest you have ever been properly absorbed in something, and what was it?
Their attention is more telling than their schedule.
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.