150 “How Well Do You Know Me?” Questions

“How well do you know me?” is the rare game that works on a first date, at a hen do, and on a sofa with someone you have lived with for eleven years. The format is simple — you write questions about yourself, someone else guesses the answers — but the quality of the questions is what decides whether it feels like a real conversation or a dull survey.

Below are 150 questions grouped by how much they reveal, from easy warm-ups to the ones that make people put their phone down. Skim them, steal the twenty that made you smile, and ignore the rest.

Warm-ups (easy, but not boring)

Start with questions your player is almost certain to get right. Early correct answers make people competitive, and competitive people pay attention.

1. 1What is my go-to coffee or tea order?
2. 2Which meal would I order at the same restaurant every single time?
3. 3Am I a morning person or a night owl — honestly?
4. 4What is the first thing I do when I get home?
5. 5What is my most-used app?
6. 6Which chore do I put off the longest?
7. 7How do I take my eggs?
8. 8What is my usual bedtime, give or take an hour?
9. 9Which shoes do I wear when I am not thinking about it?
10. 10What is my ringtone?
11. 11Do I read the reviews before I buy something, or just buy it?
12. 12What is my comfort TV show, the one I have seen enough times to fall asleep to?
13. 13Which snack disappears fastest in my house?
14. 14How many alarms do I set?
15. 15What is my coffee-to-water ratio, roughly?

Favourites and strong opinions

Favourites are the backbone of the genre because the answers are specific and arguable. If your player gets one wrong, they will want to argue about it, which is exactly the point.

1. 1What is my favourite film that I would defend in a fight?
2. 2Which album could I listen to start to finish without skipping?
3. 3What is my favourite meal that someone else cooks?
4. 4Which season do I actually like, not the one I say I like?
5. 5What is the best holiday I have ever been on?
6. 6Which fictional character do I most identify with?
7. 7What is my favourite smell?
8. 8Which biscuit is the correct biscuit?
9. 9What is my favourite thing to do on a day with no plans?
10. 10Which city would I move to tomorrow?
11. 11What is my favourite item of clothing I own?
12. 12Which song would I pick at karaoke?
13. 13What is my favourite way to spend £20?
14. 14Which takeaway do I order when I have had a bad day?
15. 15What is the best gift I have ever been given?

Habits and small tells

These are the questions that separate people who know you from people who know about you. Nobody guesses these from a social media profile.

1. 1What do I do with my hands when I am nervous?
2. 2Which word do I overuse?
3. 3How do I hold my phone when I am reading something serious?
4. 4What is the sound I make when I am pretending to listen?
5. 5Which side of the bed is mine and how strongly do I feel about it?
6. 6How long do I leave a message on read before answering?
7. 7What do I always forget when I leave the house?
8. 8How do I organise my photos, or do I?
9. 9What is my tell when I am lying about liking a present?
10. 10Do I fold or scrunch?
11. 11What is the first tab open on my laptop?
12. 12How do I react when someone sings happy birthday to me?
13. 13What do I do when I cannot sleep?
14. 14Which drawer in my house is the chaos drawer?
15. 15How many browser tabs is a normal Tuesday for me?

Shared history (for people who have one)

This is the round that makes the game feel like a gift rather than a test. Every question is about a moment you both lived through, so even a wrong answer starts a story.

1. 1Where were we the first time we met?
2. 2What was the first thing I said to you?
3. 3Which trip of ours went most wrong, and was most fun?
4. 4What did we eat on our first proper meal together?
5. 5Which argument do we still bring up as a joke?
6. 6What song was playing more than any other the summer we met?
7. 7Which of my friends did you like immediately?
8. 8What is the longest we have gone without speaking?
9. 9Which photo of us is my favourite?
10. 10What did you think of me for the first ten minutes?
11. 11Which house or flat of mine did you like best?
12. 12What is a thing I did for you that you have never mentioned again?
13. 13Where were we standing when something changed?
14. 14What is the running joke neither of us can explain to anyone else?
15. 15Which day would we both pick to live again?

The deep cuts

Use three or four of these, not fifteen. They land hardest when they arrive between lighter questions, and they are the ones people remember a week later.

1. 1What am I most proud of that I never talk about?
2. 2Which compliment have I never forgotten?
3. 3What was I most afraid of at twenty?
4. 4Which decision of mine would I make differently?
5. 5What do I worry about at 3am?
6. 6Who do I most want to make proud?
7. 7What is the kindest thing anyone has done for me?
8. 8Which version of me do you think I like best?
9. 9What do I pretend not to care about?
10. 10Which loss changed how I think?
11. 11What would I do with a year off and no obligations?
12. 12Which habit do I most want to break?
13. 13What do I need when I am upset, practically speaking?
14. 14Which of my own qualities do I underrate?
15. 15What do I hope is true about me in ten years?

Silly ones, for pacing

Every quiz needs a release valve. Drop one of these in after a heavy question and the whole thing keeps moving.

1. 1Which animal would I be in a fight, realistically?
2. 2What would my wrestling entrance music be?
3. 3How would I do in a zombie apocalypse, on a scale of one to ten?
4. 4Which conspiracy theory could I be talked into?
5. 5What is my useless superpower?
6. 6Which historical figure would I refuse to have dinner with?
7. 7What would I call a boat?
8. 8Which two foods would I never combine?
9. 9What is my villain origin story?
10. 10Which reality show would I win?
11. 11How many push-ups can I do before I lie about it?
12. 12What is the worst haircut I have had?
13. 13Which cartoon character annoys me most?
14. 14What would be on my novelty tea towel?
15. 15Which of my opinions is objectively wrong?

How to structure the questions you picked

Order matters more than people expect. A good structure looks like this:

1. 1Three warm-ups, so they get a run of correct answers.
2. 2Four or five favourites, where the arguing starts.
3. 3Two habits or small tells, which is where they realise this is not a generic quiz.
4. 4A silly one, to reset the mood.
5. 5Three or four shared-history questions, the emotional core.
6. 6One deep cut, placed second from last so it has room to land.
7. 7A final easy question, so the game ends on a win.

For multiple choice, write one obviously right answer, one plausible decoy, and one that is funny to anyone who knows you. The joke option is doing real work — it is what makes people read the question twice.

Scoring, and what to do with the score

Percentages are fine but titles are better. Give the score a name: under 40% is “met at a wedding once”, 40–70% is “solid acquaintance with ambitions”, 70–90% is “genuinely paying attention”, and anything above that gets “frankly a little unsettling”. People screenshot titles. They do not screenshot 68%.

If you are sending this as a present, put something at the end that only appears once they finish — a photo, a playlist, a letter, a voucher. The quiz becomes the wrapping paper rather than the gift itself, and the whole thing takes about fifteen minutes to build.