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

Questions to ask your boyfriend, by the moment you’re in.

Curated prompt sets for the conversations that actually happen. First three months, year one anniversary, before getting engaged, after a fight. Thirty per moment, hand-edited, no fluff.

Start with: Early relationship Start with: Year one and beyond

You have probably seen the lists with two hundred and seventy 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 trying to know better. They are organised by Pinterest categories, juicy, spicy, flirty, and they expect you to scroll for thirty minutes and screenshot two questions you might use.

So we made a different thing. About thirty questions per moment, hand-edited, organised by the conversations that actually happen. The first three months. The first big fight. The year-one anniversary. Before getting engaged. And the harder one, what to do when the answer surprises you.

We hold things back on purpose. The web shows the curated thirty, the app, when it ships, will deliver two hundred more per stage with shuffle, save, and a paired mode where you both answer privately and compare. 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.

Early relationship

First three months

When you are still figuring out whether this has legs and you want to know more without sounding like an interview.

Becoming exclusive

The are-we-official conversation, asked plainly. Not a confrontation, not a hint either.

To know him better

Months three to nine, no specific event, just curiosity practice and gentle calibration.

Going deeper

Deep questions, done well

The deep questions search, answered honestly. Vulnerability invitations, not extractions.

The money conversation

Most money fights are not about money. They are about the meaning of money. Map the meaning first.

Talking about the past

Exes, family, formative friendships. The pattern, not the gossip about the woman before you.

The milestones

First holiday together

Travel reveals how someone handles small irritations and the absence of routine. Use the trip as a conversation surface.

Before moving in

A relationship-arc decision dressed up as logistics. Practical and emotional, both load-bearing.

Year one anniversary

Half retrospective, half forward looking. The first checkpoint that actually matters.

Year two and beyond

The years where the public conversation about your relationship goes quiet. The private one matters more.

The big one

Before getting engaged

Eight load-bearing topics, thirty-two prompts, the most consequential conversation in the relationship arc.

The 21 questions game, done well

A specific game format, in a deliberate sequence. For early dating, road trips, late-night calls.

The hard ones

After a fight

Repair mode, not post-mortem. Twenty prompts, deliberately fewer than other pages. Used carefully.

How to use these prompts

When in the night, how to introduce one without sounding like an interview, what to do if he deflects.

The questions to skip

The wrong question at the wrong age of the relationship is more damaging than no question at all.

The app, when it ships

Each of the pages above shows the curated thirty. The app delivers two hundred more per stage, plus shuffle, save, and a paired mode where you both answer privately and compare.

We are building it now. Find out when it is ready, no email gate, no popups.

If you are reading this from his side, the boyfriend’s mirror is at questionstoaskyourgirlfriend.com. If you are still at the does-this-have-legs stage of dating, the date-stage prompts are at questionstoaskonadate.com. Pre-confirmation, the crush-stage signal-reading prompts are at questionstoaskyourcrush.com.