21 questions
Pick who's playing and how bold to go, and we'll deal 21 questions for one person to answer.
- Pick who answers first.
- The others take turns asking until all 21 are done.
- Answer honestly and skip one at most. Then swap.
All 74 questions for the game
Light
- What was your first job?
- Can you quote a whole movie almost word for word? Which one?
- Who was your celebrity crush growing up?
- Which fictional world would you move to tomorrow?
- Did you have a nickname growing up? Where did it come from?
- Which pet peeve drives you up the wall?
- What's the last photo you took that you'd happily show everyone?
- Has anyone ever told you that you look like someone famous?
- Which three things would you take to a desert island?
- What's your go-to karaoke song?
- Would you ever go on a trip with a group of strangers?
- If you could be 20 in any decade, which would you pick?
- Who did you see at your first concert?
- Name the weirdest thing in your fridge right now.
- If you could swap jobs with anyone for a day, who would it be?
- How embarrassing was your first email address?
- What do you always carry in your bag?
- Which TV family is most like yours?
- If you were an animal, which one would you be?
- As a kid, what did you believe that turned out to be completely wrong?
- Would you ever dye your hair bright blue?
- Which everyday thing are you surprisingly bad at?
- Where did you go on your first trip without your parents?
- Is there a chore you secretly enjoy?
- What's the most impulsive thing you've ever bought?
- Which word from your hometown does nobody else seem to get?
- What was the first thing you ever cooked on your own?
- Have you ever read the last page of a book first?
- Describe the weirdest dream you can still remember.
- Who's the most famous person you've ever met?
- Which emoji do you overuse?
- What's the longest phone call you've ever had, and who was it with?
- What would people be surprised to hear you've never done?
- How bad was your worst haircut?
- Would you ever drop everything to open a tiny shop? What would it sell?
- When you get home, what's the first thing you do?
- If you got a superpower that only worked on Tuesdays, which would you pick?
- Who's the funniest person you know?
Deep
- Who knows you better than anyone?
- What makes you lose track of time?
- Which piece of advice do you give people most often?
- Which book changed your mind about something?
- What are you most curious about right now?
- How long have you known your oldest friend?
- What do you find beautiful that other people walk right past?
- When do you feel most confident?
- Who's someone you've never properly thanked?
- Which lesson took you way too long to learn?
- Which skill did you teach yourself that you're proud of?
- Which compliment would you love to hear more often?
- What's your favorite memory of us?
- What do you hope never changes between us?
- Name one thing you'd love us to do together this year.
- What are you grateful for today?
- If every day had one extra hour, how would you use it?
Bold
A little daring, never explicit
- When did you last get butterflies over someone?
- When did you last tell a white lie, and what was it?
- Have you ever made the first move? How did it go?
- What's the most cringey thing you did as a teenager to look cool?
- What's a rumor about you that turned out to be true?
- What makes you blush?
- Out of 10, how good is your flirting?
- Where did your first kiss happen?
- Which song would you dedicate to your crush right now?
- What's a tiny thing that's an instant dealbreaker for you?
- What's the cheesiest thing you've ever done for someone you liked?
- What's a dare you'd say yes to right now?
- Have you ever written a love letter, or gotten one?
- What's something you find attractive that most people don't?
- What's your most controversial food opinion?
- Have you ever been asked out by a total stranger?
- What's the most embarrassing thing you've done in front of a crush?
- Have you ever had a crush on one of your friends?
- What's the boldest thing you've ever worn in public?
Questions about the questions
How do you play 21 questions?
One person answers 21 questions in a row while the others take turns asking. Answer honestly, skip one at most, then swap. With two people, like on a date, you can take turns question by question instead.
Can you play 21 questions on a date?
Yes. Tell the generator you're with a date, and the questions stay a little flirty at most, never explicit.
Try them on new people
Every week Timeleft seats small groups of strangers for dinner, coffee or a walk, with conversation prompts built in.