Deep questions for couples

Deep questions are the hardest kind to write and the easiest to get wrong. Ask about someone’s biggest fear and they will say spiders. Ask what they avoid that they know is irrational, and you get a real answer.

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Why the usual ones fail

The standard deep-question list is mostly job interview material. Describe yourself in three words. What is your biggest regret. These sound serious and produce nothing, because they are too large to answer and everybody has a prepared response.

The questions here are narrower on purpose. Not "what are you proud of" but "what is something you are proud of that nobody else noticed". Not "what would you change" but "what would you redo knowing it would turn out exactly the same". The narrowing is what makes them answerable.

Setting up for it

Deep questions need a bit of runway. Starting an evening with the heaviest card in the deck rarely works; people need a few easy exchanges before they will risk a real one.

Play a short round of something lighter first, or set the intensity low for the first few cards and move it up. The app applies the change from the next card onwards, so you can steer as you go.

The other thing that helps is not treating an answer as a problem to solve. Most of these want to be heard rather than fixed, and reaching for a solution is the fastest way to end the conversation.

What to expect

Some cards will produce a shrug. That is normal and not a failure of the question — it usually means it landed at the wrong moment. Skip it and it will come back around another evening.

The ones that work tend not to feel dramatic. They feel like finding out something small and specific that reframes a lot of other things you already knew.

Give it a proper length, too. Six of these in an evening is plenty, and stopping while there is still something left to say is better than reaching the end of the deck.

20 truth questions

1.What's a small thing I do that you'd miss if I stopped?
2.What's something about me you'd never change, even if I asked?
3.What did you want to be at ten, and what happened to that plan?
4.What's something you're proud of that you never talk about?
5.When did you last change your mind about something that mattered?
6.What do you avoid doing that you know is completely irrational?
7.What's something you'd redo, knowing it would turn out the same?
8.What are you good at that never comes up?
9.Who shaped how you think, and have you ever told them?
10.What's a compliment you received that you still think about?
11.What's something you've wanted us to try but never actually suggested?
12.Where do you want to be living in ten years, and what's it near?
13.How do you actually want to be treated on a day you're in a bad mood?
14.What's something you've changed your mind about in the last two years?
15.When something goes wrong, do you want fixing or listening first?
16.What's a tradition from your childhood you'd want to keep going?
17.Do you apologise quickly or need time first? Which do you prefer from me?
18.What's something ordinary about your day you wish I could just watch?
19.What's the hardest part of this that you've never actually said to me?
20.What keeps you steady on the weeks when the distance is heaviest?

6 dares

21.Tell someone here one specific thing you admire about them.
22.Describe the version of yourself you're working towards, out loud.
23.Say something you've been meaning to say to someone in this room.
24.Say one thing you'd want agreed before moving in with anyone.
25.Say the thing you were going to save for later. Now.
26.Tell me one thing you have never said out loud but have thought often.

Play with the full set

These are a sample. The game has the rest — no signup needed.

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Common questions

Are deep questions a good idea for a new relationship?

Some are. Early on the useful ones are about how someone thinks rather than what has happened to them. Save the material about family and regret for later; it lands very differently once there is trust to hold it.

What if my partner gives short answers?

Ask the follow-up rather than the next card. "What made you say that" does more work than any question in the deck. Short answers are usually a first draft.

Can this replace a real conversation?

No, and it is not meant to. These are conversation starters, not therapy and not advice. If something serious surfaces, the right response is to keep talking, not to keep playing.