21 Questions Game
106 questions · By Dima Tretyak, creator of DeepTalk · Updated
21 Questions is a simple game for two. One person asks up to 21 questions, the other answers every one honestly, and then you switch. There's no board, no score and no winner. People play it on dates, on long drives, with a new friend and, very often, over text.
The questions below start funny and get more personal as you go. There are flirty and deep rounds, questions to ask a guy or a girl, a round for couples, juicy questions for adults and a set written for texting. Pick 21 from any mix of sections, or let the other person choose the section.
Funny 21 questions
Light and a little embarrassing, so the game starts with a laugh. Use a few of these before anything personal.
- 1What's the silliest injury you've had to explain to a doctor?
- 2Which celebrity do people say you look like, and do you see it?
- 3What's a food you pretended to like for way too long?
- 4What party trick do you pull out when a night gets slow?
- 5Who's the last person you looked up online, and how far back did you scroll?
- 6What nickname did you have growing up, and who gave it to you?
- 7What's a word you mispronounced for years before anyone told you?
- 8What's the worst haircut you've had, and is there photo evidence?
- 9What album did you wear out as a teenager that you'd never play in front of friends now?
- 10What's the most ridiculous thing you've cried over?
- 11What's a trend you followed that you'd like everyone to forget?
- 12What's the strangest thing in your search history right now?
Flirty 21 questions
21 Questions is a popular way to flirt because the rules give you permission to ask. These are playful, not explicit, and work on a date or over text.
- 13What did you think I'd be like before we actually talked?
- 14What's the most attractive thing someone can do without trying?
- 15What's your go-to move when you like someone?
- 16Where would you take me if we had one free evening and no budget?
- 17What's something small that instantly makes you blush?
- 18What's the best compliment you've gotten from someone you liked?
- 19What made you want to keep talking to me?
- 20What would we do on a second date that you'd never suggest on a first?
- 21Who do you think was more nervous when we first started talking?
- 22What do you notice first when someone walks into a room?
- 23What outfit makes you feel most confident?
- 24What's a song you'd put on if you wanted to set the mood?
Rather play than scroll? DeepTalk deals these out one card at a time.
Deep 21 questions
For later in the game, when the funny questions have done their job. Give the other person time to think, and answer your own questions too. More in deep questions.
- 25What's something you believed about yourself at 18 that turned out to be wrong?
- 26Who knows you best, and how did they earn that?
- 27Which of your accomplishments never made it onto social media?
- 28What would you change about how you spend your time if nobody would judge you?
- 29Who's someone you lost touch with that you still think about?
- 30Where were you the last time you completely lost track of time?
- 31What part of your personality took you the longest to accept?
- 32What topic could you talk about for an hour without notes?
- 33What's the kindest thing a stranger has done for you?
- 34What were you afraid of five years ago that doesn't bother you now?
- 35What's something you've forgiven someone for without ever telling them?
21 questions to ask a guy
Questions that get a guy talking about his friends, his hobbies and the stuff he's quietly proud of. They work on a date or with a new friend. For a partner, see questions to ask your boyfriend.
- 36What's the best advice your dad or a father figure ever gave you?
- 37Which friend would you call to help you move a couch at midnight?
- 38What hobby would you spend serious money on if nobody judged you?
- 39What's something guys rarely get complimented on that you'd love to hear?
- 40What was your dream job at twelve, and how close did you get?
- 41What movie have you rewatched more times than you'd admit?
- 42What's the most impressive thing you've built, fixed or cooked?
- 43When was the last time you got really nervous about something?
- 44How do you act when you're stressed, and what actually helps?
- 45What game or sport are you way too competitive about?
- 46What would your friends be surprised to learn about you?
- 47What's a skill you secretly wish you'd learned as a kid?
21 questions to ask a girl
Questions about her people, her plans and what makes her feel at home. Good for a first date or a new friendship. For a partner, try questions to ask your girlfriend.
- 48What's the most chaotic trip you've taken with your friends?
- 49Who do you go to when you need a straight answer?
- 50What book or show would you recommend to someone who wants to understand you?
- 51What's a small luxury you'd never give up?
- 52Which of your habits did you get from your mom or grandmother?
- 53What's the boldest thing you've done that surprised everyone?
- 54What's your comfort meal after a bad day?
- 55What's the nicest thing you found out someone said about you behind your back?
- 56What do people assume about you that's completely wrong?
- 57What's the most spontaneous decision you've ever made?
- 58Which place makes you feel completely at home?
- 59What goal are you quietly working toward this year?
21 questions for couples
Couples play 21 Questions too, and you'll still hear things you didn't know. These are about your story together. For more, see questions for couples.
- 60When did you realize you were falling for me?
- 61Which of our dates would you relive if you could?
- 62What's a habit of mine you found weird at first but love now?
- 63What's one thing we do together that you'd never want to stop?
- 64When did you first feel completely comfortable around me?
- 65What trip haven't we taken yet that you keep thinking about?
- 66What's the funniest argument we've ever had?
- 67What do you think our friends say about us when we're not around?
- 68What's a small thing I do that makes your day better?
- 69What's something new you'd like us to try this year?
- 70Which song reminds you of us, and why?
- 71What did you tell your friends about me after our first date?
Juicy 21 questions for adults
The spicy round, sometimes called freaky 21 questions. Crushes, secrets and bold moves, nothing graphic. Save it for someone you're comfortable with, and either of you can pass.
- 72What's the most daring thing you've done on a date?
- 73Where's the most unusual place you've been kissed?
- 74What's a dream date you've never told anyone about?
- 75What's the boldest text you've ever sent to someone you liked?
- 76Who was your most unexpected crush?
- 77What's the cheesiest pickup line that actually worked on you?
- 78What do you find attractive that most people wouldn't?
- 79What's the most dramatic exit you've made from a date?
- 80What's the wildest thing you've done at a party?
- 81What's your biggest turn-off on a first date?
- 82What's a secret you've only told one person?
- 83What rule have you broken for someone you were into?
21 questions to get to know someone
Friendly and easy to answer, for someone you just met. Each one gives you something to ask about next.
- 84What's a Saturday routine you'd never get tired of?
- 85Where did you grow up, and what was it like?
- 86What are you really good at that never comes up in conversation?
- 87What are you most excited about this month?
- 88What's a place you've visited that you'd move to tomorrow?
- 89What's a family tradition you still keep?
- 90How would your friends describe you in three words?
- 91What's the highlight of your week that nobody has asked you about yet?
- 92What cause would you give up a weekend for?
- 93How do you like to recharge after a long week?
- 94Which friend can make you laugh just by looking at you?
- 95What podcast, show or book have you been into lately?
21 questions over text
Short questions that are easy to answer from a phone, and some you can answer with a photo or screenshot. Send one, wait for the answer, then send the next.
- 96What's the last photo you took, and can you send it?
- 97What's the last voice note you sent, and who got it?
- 98Which three emojis sum up your day so far?
- 99What's the most recent song you added to a playlist?
- 100What's the last thing you bought that you didn't need?
- 101What's your phone wallpaper, and what's the story behind it?
- 102Who do you text the most, family not included?
- 103What's the strangest notification you've gotten this week?
- 104Which app eats most of your screen time?
- 105What's the name of a group chat you're in that needs explaining?
- 106What's one thing you'd want me to know before we meet in person?
How to use these questions
- Decide who goes first. That person asks up to 21 questions, one at a time.
- The other player answers every question honestly. Agree before you start that each of you can pass once or twice.
- When the 21 questions are used up, switch roles and the other person asks.
- Start with funny or get-to-know questions and save the flirty, deep and juicy ones for later in the round.
- Over text, send one question at a time and wait for the answer before the next.
- Follow up when an answer is interesting. A good follow-up can count as one of your 21.
Play them as cards instead
DeepTalk deals questions like these one card at a time, with 20 decks and over 2,000 questions for couples and friends.
Frequently asked questions
How do you play 21 Questions?
Two people take turns. One asks up to 21 questions and the other answers each one honestly. Then they switch, so both get to ask. There's no winner and no fixed list of questions, which is why people play it on dates, with new friends and over text.
What are some good 21 Questions?
Open questions that lead to a story, like "What's a food you pretended to like for way too long?", "Where were you the last time you completely lost track of time?" or "What did you think I'd be like before we actually talked?" Mix funny, flirty and deep ones, and avoid questions that can be answered with yes or no.
What are some juicy 21 Questions?
Questions about crushes, secrets and bold moves, like "Who was your most unexpected crush?", "What's the boldest text you've ever sent to someone you liked?" or "What's a secret you've only told one person?" Save them for someone you're comfortable with and let either player pass.
Is 21 Questions a dating game?
Not only. Friends, couples and people who just met all play it. It's popular for flirting, though, because it lets you ask personal questions without it feeling like an interview. Many people play it over text with a crush or on an early date.
Is 21 Questions the same as 20 Questions?
No. 20 Questions is a guessing game: one player thinks of something, and the others ask up to 20 yes-or-no questions to figure out what it is. 21 Questions is about getting to know each other, and the questions can be about anything.
Can you play 21 Questions over text?
Yes, it's one of the most common ways to play. Send one question at a time and wait for the answer before the next. Questions that can be answered with a photo or a screenshot, like the ones in the "over text" section above, keep the chat moving.
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