100 “How Well Do You Know Your Friends?” Questions

Everyone has that one friend who swears they know you better than you know yourself. These questions are how you find out if they’re right.

Below are three ways to play, followed by 100 questions sorted from easy warm-ups to deeper cuts. Every question is about one friend: the others guess, the friend confirms, and the arguments start. Stuck for where to begin? Use the random question picker above.

How to play with these questions

You don’t need anything except the questions and a way to keep score. Here are three formats, from most structured to most chaotic.

1. The classic quiz

1. Pick one person to be “in the hot seat”.
2. Read 10 questions about them aloud.
3. Everyone else writes down their guess for each one.
4. The person in the hot seat reveals the real answers. One point per correct guess.
5. Rotate until everyone has been in the hot seat.

Best for: 3 to 6 people who all know each other fairly well.

2. Head-to-head

Two friends sit back to back. You read a question about one of them, and both write an answer: the subject writes the truth, the other writes their guess. Matching answers score a point. It’s a great tiebreaker, and great at revealing which “best friends” have been bluffing for years.

3. Pass the phone

Put everyone’s names in a hat, or let an app do it. Whoever holds the phone draws a question about another player, the whole room debates the answer, and the guesser makes the final call. Right answer, one point. Then the phone moves on. This keeps everyone involved instead of waiting for their turn, and it scales to big groups.

This is exactly how Fact Or Else works: the app picks who goes next, fills in a friend’s name, and keeps score so nobody has to.

Easy warm-up questions

Start here. These are low-stakes and quick to confirm, which gets everyone into the rhythm of guessing.

1. What’s their go-to takeout order?
2. Are they a morning person or a night owl?
3. What’s the first app they open in the morning?
4. Would they rather go to the beach or the mountains?
5. What’s their comfort TV show?
6. Do they reply to messages instantly or three days later?
7. What’s their favorite season?
8. Coffee, tea, or neither?
9. What would they pick as their last meal?
10. Are they always early, on time, or fashionably late?
11. What’s their karaoke song?
12. Cats or dogs?
13. How many unread notifications do they have right now: under 10, under 100, or more?
14. What’s the snack they can’t stop buying?
15. Would they rather watch the movie or read the book?
16. What’s their favorite way to spend a free Sunday?
17. Window seat or aisle seat?
18. Which emoji do they use the most?
19. What’s their go-to excuse for leaving a party early?
20. Pineapple on pizza: yes or no?

“Would they?” questions

These ask how your friend would react in a situation. Nobody can look the answer up, which makes for the best debates.

1. Would they survive a week without their phone?
2. Would they eat something off the floor if nobody was watching?
3. Would they rather be famous or rich?
4. Would they go skydiving if someone paid for it?
5. Would they tell a friend about something stuck in their teeth?
6. Would they survive a zombie apocalypse for more than a day?
7. Would they rather lose their phone or their wallet?
8. Would they sing in front of a crowd of strangers?
9. Would they rather live in the city or the countryside?
10. Would they return a wrong order at a restaurant or just eat it?
11. Would they go on a reality TV show?
12. Would they rather be able to fly or be invisible?
13. Would they read someone else’s diary if they found it open?
14. Would they rather never use social media again or never watch TV again?
15. Would they cry at a sad commercial?
16. Would they win a game of hide and seek?
17. Would they rather have a personal chef or a personal driver?
18. Would they move abroad for a year if they got the chance?
19. Would they rather know the future or change the past?
20. Would they finish a 1,000-piece puzzle or give up halfway?

“Have they ever?” questions

These are about your friend’s history. The subject has to answer honestly, so only use the ones your group is comfortable with.

1. Have they ever fallen asleep in a cinema?
2. Have they ever sent a message to the wrong person?
3. Have they ever pretended to be on the phone to avoid someone?
4. Have they ever cried at a wedding?
5. Have they ever been on TV, even in the background?
6. Have they ever broken a bone?
7. Have they ever forgotten a close friend’s birthday?
8. Have they ever laughed so hard they cried in public?
9. Have they ever got lost in their own city?
10. Have they ever won a competition?
11. Have they ever re-gifted a present?
12. Have they ever stayed up all night?
13. Have they ever walked into a glass door?
14. Have they ever binge-watched a whole series in one weekend?
15. Have they ever pretended to know a song they’d never heard?
16. Have they ever met a celebrity?
17. Have they ever been told off by a teacher for laughing?
18. Have they ever cut their own hair?
19. Have they ever lied about their age?
20. Have they ever been the last to leave a party?

Favorites and firsts

Specific answers make these harder. Decide in advance whether “close enough” counts.

1. What was their first phone?
2. What’s their favorite movie of all time?
3. Who was their childhood celebrity crush?
4. What was the first concert they went to?
5. What’s their favorite word?
6. What was their dream job as a kid?
7. Where was their first holiday abroad?
8. What’s their favorite smell?
9. What was the first video game they got hooked on?
10. What’s the best gift they’ve ever received?
11. Which fictional character are they most like?
12. What’s their favorite board game?
13. What was their first job?
14. Which song do they always skip?
15. What’s their least favorite chore?
16. What’s their favorite school subject they’d never admit to?
17. Who was their first best friend?
18. What’s their favorite city they’ve visited?
19. What’s their most-used phrase?
20. What’s the first thing they’d buy if they won the lottery?

Deep cuts

Save these for later in the game, when everyone’s warmed up. They’re still fun, but they reward the friends who actually listen.

1. What are they secretly most proud of?
2. What’s the one thing that always cheers them up?
3. What’s a small thing that annoys them more than it should?
4. What would they do with a completely free year?
5. Who do they call first with good news?
6. What’s a skill they wish they had?
7. What’s their biggest pet peeve in friends?
8. What’s a fear they’d never admit to at a party?
9. What would their perfect day look like, start to finish?
10. Which decade would they live in if they could choose?
11. What’s the best advice they’ve ever been given?
12. What’s something they’re surprisingly good at?
13. Where do they see themselves living in ten years?
14. What do they do when they can’t sleep?
15. What’s one thing on their bucket list?
16. Which friend in this room have they known the longest?
17. What’s their love language: words, gifts, time, help, or hugs?
18. What’s a hill they’d die on?
19. What would they name their autobiography?
20. What’s something they’ve changed their mind about in the last year?

Tips for a great round

• Agree on a skip rule. Anyone can pass on a question about themselves, no explanation needed. It keeps the game fun for everyone.
• Let the subject be the judge. If the answer is “sort of right”, the subject decides whether it counts.
• Mix difficulty. Two easy questions, then a deep cut, keeps the energy up.
• Steal points. If the main guesser gets it wrong, let anyone else shout the right answer for half a point.
• Write your own. The funniest questions are the ones about your group’s inside jokes. Use the formats above (“Would they…?”, “Have they ever…?”) as templates.

Keep score without the paperwork

Pen and paper works fine for four people. With ten, the scoring gets messy fast. In Fact Or Else you add everyone’s names once, pick question packs, and pass one phone around: the app picks who goes next, puts a friend’s name into each question, and shows the final leaderboard, including who knew their friends best. You can also write your own questions and drop any player’s name into them.