Shifting into something: when the crush stage is ending and dating is starting.
The crush stage is ending when one or both of you has used the word “date”, or when there is a regular pattern of seeing each other one-on-one with intent. The prompts at this moment are different from crush-stage prompts because the asking-and-ambiguity has resolved; the conversations are now about whether this is going to be a thing.
The list below has twenty prompts in four sections, deliberately fewer than the other moment pages. This is a transition page, not a stand-alone library. Once the dating arc is clearly underway, the on-the-date prompts pick up at questionstoaskonadate.com; if the dating arc has tipped into something exclusive, the in-relationship prompts are at questionstoaskyourboyfriend.com and questionstoaskyourgirlfriend.com.
Read how to use these prompts for technique notes that apply across the cluster.
What is this becoming
The prompts in this section name the in-between, gently. The crush stage is ending; dating has not quite begun in name. The prompts let both of you describe what is happening without having to decide it yet.
What is the version of what we are doing that you would want, if you could choose it?
Asks them to describe the shape they want, in their words.
What is the thing about how this is going that has surprised you, in a good way?
Surprise-as-pleasure prompt. Lets them name the good, without overclaiming.
What is the kind of relationship that you are drawn to, when you actually think about it?
Lets them describe what they want, structurally, without it being about you specifically.
What is the next step from here that would feel right rather than rushed?
Right-not-rushed is the discipline. Invites pacing into the conversation.
What is the version of us in three months that you would be most pleased with?
Three months is the right unit, longer than a date, shorter than a future. Specific and imaginable.
Do we want the same kind of thing
Gently testing whether you both want the same shape. The point is not to extract a commitment, it is to find out whether the trajectory is shared.
What is the kind of dating you find yourself most pleased with, when it works?
Asks for their pattern, not a pledge.
What is the thing you want from a relationship that you have learned to be honest about, even when it is not glamorous?
The unglamorous-and-honest answer is the most useful kind.
What does it look like when you start to feel really comfortable with someone?
Lets them describe their settling-in process. You are listening for whether they recognise it happening here.
What is the kind of pace that suits you when something is starting?
Pace conversation, asked plainly. Almost no one asks this and most people have an answer.
What does going slow mean to you, in a way that is not a brush-off?
Asks for their actual definition rather than the abstract one.
What do you want from this stage
Naming the stage explicitly. These prompts are the bridge between calibration and dating. They assume you are both willing to call this what it is.
What is the version of the next month with us in it that you would be most pleased with?
Asks them to imagine the immediate future, together. Specific and concrete.
What is the part of dating you find yourself most pleased with, generally?
Lets them describe their dating self, without making it about you specifically.
What is the kind of conversation you want to be able to have with someone you are dating?
Sets up the conversation you are already trying to have.
What is the next thing you are looking forward to, that I might be involved in?
Direct in a soft way. Almost no one will refuse to answer this if the moment is real.
What is something you would want me to know about you, that has not really come up yet?
An invitation to bring something forward, deliberately. Useful when both of you are leaning in.
What would make this work
The bridge to the in-relationship pages. These prompts ask about the conditions, not the destination. They assume something is forming and want to make sure it forms well.
What is something that has made a previous relationship better than it would have been otherwise?
Their own positive precedent. Listen for the specific thing they value.
What is a thing you have done in dating that you have been pleased with yourself for?
Lets them brag a little, gently. Tells you what they consider good behaviour.
What would make this kind of stage feel safe for you, rather than precarious?
Safety-not-precarious is the keyword. The honest answer is the most useful kind.
What is the kind of small attention from someone you have been dating that lands hardest with you?
Tells you how to show up, in their words.
What would you want me to do, if either of us starts to feel a wobble about this?
Names the future wobble in advance. The naming is the work.
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.