A library of conversation prompts for the moments that actually happen on a date.

Questions to ask on a date, by the moment of the date you are in.

Curated prompt sets for the conversations that actually happen on a first, second, or third date. The first ten minutes. The food on the table. The walk back. The second-date shift. Twenty-five per moment, hand-edited, no fluff.

Start with: First date Start with: Second date

You have probably already seen the lists with one hundred and sixty questions on them. We have read them too.

Most of those questions are filler, written for SEO rather than for you and the person you are about to meet. They are organised by Pinterest categories, juicy, spicy, twenty-one questions, and they expect you to scroll for thirty minutes and screenshot two questions you might use.

So we made a different thing. About twenty-five questions per moment of the date, hand-edited, organised by the conversations that actually happen. The first ten minutes, before either of you has decided whether to relax. The food on the table, when the pressure has dropped. The walk back, when the eye-contact eases. The second-date shift, when the prompts can do a little more work. And the harder ones, the questions to skip when the date is too early for them.

We hold things back on purpose. The web shows the curated twenty-five. The app, when it ships, will deliver two hundred more per moment, with shuffle, save, and a pre-date primer mode. The point is not volume. The point is that the questions you came here for are the ones we have already chosen.

The library

Choose the moment you are in.

Before the date

Pre-date primer

The date is in two hours and you are already a bit nervous. Not a question list, a primer. Three openers, three back-pocket prompts, three things to listen for.

First-date moments

The first ten minutes

When neither of you has decided whether to relax yet, and the wrong opener locks you into small talk for the rest of the night.

Mid-meal questions

The food has arrived, the bar phase is over, and the conversation is about to settle. The prompts that work once both of you are eating.

Walking and talking

Side-by-side instead of face-to-face. The eye-contact pressure drops, the prompts can be slightly more open-ended, the silences can hold a little more.

The second and third date

The second-date shift

From tell-me-about-yourself to let-me-hear-how-you-think. The prompts shift, the depth increases, the calibration begins.

Third-date depth

The assessment phase tapers, the now-what phase begins. Prompts that test alignment without sounding like an interview.

Becoming something more

The are-we-doing-this-exclusively conversation. Direct without being confrontational, the prompts that name the moment plainly.

Going deeper, by intent

Deep questions, done well

Deep does not mean heavy. Deep means specific. Thirty prompts organised by depth gradient, with a flag on the ones that belong to date three.

To know them better

Curiosity practice, organised by category of intent. What makes them light up, how they think about people, what they do alone, the version they are working on.

Values and direction

Money, family, ambition, conflict, what they do not want. Calibration without an intake form. Usually date three or four.

The lighter side and signals

Fun and flirty, not from TikTok

Specific, embodied, slightly weird, kind. The flirty section is divided into date-one and date-two-or-three. Thirty prompts, no would-you-rather.

Reading the signals

Three signs the date is going well, three signs to be honest about, and five prompts that surface their experience of the date in a way they cannot easily perform.

Date-night questions

For the couple who already knows each other. Not first-date prompts, the ones that work between people who have a shared backlog to revisit.

Meta and discipline

The 36 questions, on a date

How the Aron framework actually works, where it does not, and which of the original thirty-six are reasonable for a first, second, or third date.

How to use these prompts

Most lists stop at the list. The list is the easy part. What to do with it on an actual date is the hard part.

The questions to skip

The wrong question on a first date is more damaging than no question at all. A short, opinionated discipline page.

The app, when it ships

Each of the pages above shows the curated twenty-five. The app delivers two hundred more per moment, plus shuffle, save, a pre-date primer mode, and a turn-based prompt-and-answer mode for the two of you to play.

We are building it now. Read more on the about page, no email gate, no popups.

If you are still pre-meet and trying to read whether they are even interested, the crush-stage signal-reading prompts are at questionstoaskyourcrush.com. If the dating arc has shifted into something exclusive, the in-relationship prompts are at questionstoaskyourboyfriend.com and questionstoaskyourgirlfriend.com.