Emotional Closeness

105 How Well Do You Know Me Questions

8 September 2026 · 8 min read

"How well do you know me" is usually played wrong. Someone reads a question aloud, the other person guesses, and the asker immediately says whether it was right. Within five questions it has turned into a test with a grade attached, and whoever is losing stops enjoying it.

The version that works is scored properly and answered blind. Each of you writes your own real answers to the same list. Then each of you guesses the other's. Nobody sees anything until both are finished. You compare at the end, once, and the score covers the whole set rather than being announced question by question.

That structure matters more than the questions do. It removes the running commentary, it stops either of you adjusting mid-game, and it means a wrong guess is a data point in a total rather than a small public failure.

How to score it

Give a point for each guess that matches their real answer. Sixty per cent is a good score for a couple of a few years. Ninety is unusual and normally means you have played something like this before.

The interesting number is not the total. It is the gap between the two totals. If one of you scores eighty and the other fifty, that asymmetry is the finding — one person has been paying more attention, or has been easier to read, and both of those are worth talking about.

Also mark, separately, any question where you guessed wrong and were confident. Those are worth more than the score. Being wrong is normal; being certain and wrong is where the assumptions live.

The basics

Everyone should get most of these. If a couple is missing several here, that is genuinely informative.

• What is their exact order at their usual coffee place?
• Which side of the bed do they need?
• What time do they actually want to go to sleep?
• What do they eat when nobody is watching?
• What is the one food they will not eat?
• How do they take their tea?
• What size shoe do they wear?
• What is their middle name?
• Where were they born?
• How many siblings do they have, and where do they fall?
• What was their first job?
• What did they study, or want to?
• What is their phone's screen background?
• Which parent are they more like?
• What is the last thing they bought for themselves?

Preferences and habits

• Do they read the reviews before booking anything, or not at all?
• Do they unpack immediately on arriving somewhere, or live out of the bag?
• Do they make the bed?
• Do they answer unknown numbers?
• Do they reply to messages instantly or in batches?
• Do they prefer a window or an aisle?
• Do they arrive at the airport early or on the edge?
• Do they finish a book they are not enjoying?
• Do they watch something twice?
• Do they sing when they are alone?
• Do they prefer a shower in the morning or at night?
• What is the first thing they do when they get home?
• What do they do when they cannot sleep?
• Do they use a to-do list, and do they trust it?
• What is their most-used app that is not a messaging one?

What they think about themselves

This is where the score usually drops, and where the game starts being worth playing.

• What are they most proud of that has nothing to do with work?
• What do they think their best quality is?
• What do they think their worst one is?
• What compliment do they not believe when they hear it?
• What compliment lands every time?
• What are they insecure about that they have never named out loud?
• Would they say they are an optimist?
• Do they think of themselves as funny?
• What do they think other people misread about them?
• What would they change about how they look, if anything?
• Do they think they are good at their job?
• What do they secretly think they could have been good at?
• What did they believe about themselves at twenty that they no longer do?
• Are they more afraid of failing or of being seen failing?
• What do they do when they are embarrassed?

Under stress

• What is the first sign that they are stressed, before they say anything?
• Do they want to be left alone or followed when they walk off?
• Do they want advice, agreement, or silence?
• Do they eat more or less when things are hard?
• Who do they call first with bad news?
• Do they cry easily, rarely, or only alone?
• What kind of tired makes them short-tempered?
• Do they apologise quickly or slowly?
• Do they hold a grudge?
• What do they do the night before something they are dreading?
• Do they rehearse difficult conversations?
• Would they rather cancel or go and be uncomfortable?
• What do they say when they are upset but do not want to discuss it?
• How long does a bad mood usually last?
• What actually helps when they are like that — not what they say helps?

History

• What is their earliest memory?
• Who was their closest friend at fifteen, and are they still in touch?
• What is the worst job they have had?
• What is the biggest risk they have taken?
• Have they ever been genuinely frightened, and by what?
• What is a decision they still think about?
• Which of their exes shaped them most, and how?
• What did they want to be at ten?
• What was their family like at dinner?
• Who in their family are they most like, and do they mind?
• What is a thing they were praised for as a child?
• What is a thing they were criticised for that stuck?
• Where have they lived that they would not go back to?
• What is the longest they have gone without speaking to someone close?
• What is a story they tell often, and is it entirely true?

About the two of you

The hardest section, and the one where being confident and wrong is most common.

• What did they first notice about you?
• When did they know?
• What is their favourite thing about your relationship that you never do deliberately?
• What do you do that irritates them and they have never mentioned?
• What do you do that they would miss immediately if you stopped?
• Which of your habits have they quietly adopted?
• What is the nicest thing you have ever done for them, in their view rather than yours?
• What do they wish you asked about more?
• What do they think you are wrong about?
• What is the argument they think you two keep having?
• Do they think you two argue too much, too little, or about right?
• What would they change about how you two spend a free weekend?
• What do they tell their closest friend about you?
• What are they most grateful for that they have not said?
• What do they worry about, regarding the two of you?

The future

• Where do they want to be living in five years?
• Do they want children, and has that answer changed?
• Would they move abroad?
• What would they do with a year off?
• What would they do with a large amount of money, honestly?
• Do they want a wedding, and what kind?
• Are they where they expected to be at this age?
• What are they still hoping to be good at?
• What do they want less of?
• What are they putting off?
• Would they take a pay cut for something better?
• What does a good ordinary Tuesday look like to them in ten years?
• Who do they want to be closer to than they currently are?
• What do they think you two should do more of?
• What is the one question on this page they hoped you would not ask?

Why blind answering changes the result

Play this face to face and something predictable happens: the person answering watches the guesser's face, and adjusts. Not deliberately — most people are not aware they are doing it. But a partner who guesses "you'd say quality time" with obvious hope attached gets agreement more often than they have earned.

The same effect runs the other way. Someone who suspects their real answer will disappoint gives the diplomatic one instead. Both effects push the score up and the information down, which is exactly backwards.

Writing them down and comparing once removes that effect. PairReveal's Duel mode is exactly this game with the scoring automated — guesses stay sealed until both of you have finished, so nobody is grading anybody in real time.

Whichever way you play, the score is not the output. The list of questions where you were sure and wrong is.