Man in Green Jacket Sitting Beside Woman in Blue Jacket

21 Questions Game: How to Play, Questions to Ask, and More [2020]

The 21 Questions Game is a classic way to have some fun while getting to know someone better. The great thing about this game is that it’s versatile! You can play it in a group with friends, alone with a crush, or with your long-term partner because it all centers around the questions you come up with. So, if you’re looking to find a great conversation starter to get to know someone better or a personal questions game to spice up your date night, you’ve come to the right place! Look over the article below to pick your fun way to play 21 Questions and connect with the people in your life.

21 Questions Game Rules

There’s a variety of ways to play the 21 Questions Game and it’s easily adaptable to any size group. Browse the ways below to figure out how to play 21 Questions and find your favorite way to play!


Two Person Rules: In a game of 21 Questions with just 2 parties, the classic way to play is by person A asking a question while person B answers. After this question has passed, the roles reverse with person B asking the question and person A answering. This version is great for playing over social media apps like Facebook or Twitter, dating apps like Tinder or Hinge, or text messaging too!

Multi-Player Rules: When playing with 3 or more people, the classic way to play is to randomly select or have someone volunteer to be the first person to answer questions. Once that person is chosen, the group will proceed by asking them 21 questions back to back (the group decides whether follow-up questions count or not). The next person to be asked can either be nominated by the person who just finished, randomly selected, or can volunteer; it’s the group’s decision!


These game rules are strictly meant for a group setting. Here, the “game head” is appointed to ask a great question to anyone in the group. The person they ask then has to answer and ask someone else in the group a question. The game will continue like this until everyone has answered a question. Once everyone has answered their round 1 question, the group may return to the game head to begin their second round of questions and so on until 21 questions are answered by all!

Round and Round

Two Person Rules: In this version of the 21 Questions Game, a question will be brought up by person A that both parties have to answer. Once the question is answered by both people, person B then elects a question that they both must answer and so on until the game reaches 21 questions!

Multi-Player Rules: When playing this version with a group of people, the “game head” is appointed again to ask a question to the group. The person to the right of the game head answers, then the next person over, etc. until the question comes back to the game head to answer. The game head then becomes the person to the right of the last game head, and they then pose the second round question to the group.

Tips and Tricks for Game Play

  • Conversation: If the game breaks into a series of follow-up questions and conversation, let it flow! That’s the point of the game and you can always return to it by asking a good question when the talking dies down.
  • Passes: This rule is optional but if desired, each person may be appointed two passes to use when a question makes them uncomfortable or they don’t want to answer.
  • Drinking Game: A great way to take this game up a notch is to add in some fun cocktails or mocktails! Set a rule that every time someone passes, they have to drink or every time a group member says a specific word, the group has to drink.

21 Questions to Ask Your Crush

This game is perfect to play with your crush over the phone or in-person to get to know them a little better! Ask a fun question to make them laugh or an interesting question to spark a conversation and some connection between you two. Most of all, relax, have some fun, and get to know them!

  1. What’s your favorite food to eat?
  2. What’s your dream job?
  3. How old were you when you had your first kiss?
  4. What’s your favorite color?
  5. What’s a pet peeve you have that you don’t tell anyone about?
  6. What’s your favorite season of all time that you could live in for the rest of your life?
  7. What’s your favorite movie of all time that you couldn’t live without?
  8. What do you look for in a partner?
  9. What’s the longest romantic relationship you’ve ever had?
  10. What’s been your least favorite job thus far?
  11. If you could only pick three artists to listen to forever, who would they be?
  12. What’s the best piece of advice your parents ever gave you?
  13. What would your dream date look like?
  14. Who is your favorite character in… (pick a TV show or movie they like)?
  15. What was your favorite subject in school?
  16. What’s something crazy or adventurous you’ve done that you would do again in a heartbeat?
  17. A flirty question could be, “What color underwear are you wearing right now?”
  18. What’s the awkwardest date you’ve ever been on?
  19. What’s a special talent you have that you don’t share much?
  20. Who are you closest to in your family?
  21. If you could change one thing about the world, what would it be and why?

Funny 21 Questions to Ask Your Friends

When playing with a group of friends, this game can turn wildly funny very fast. Gather some snacks, invite over your best buds, and turn your boring night in, into something exciting! Look over the list below to find the right question to ask the group when it’s your turn.

  1. What’s the weirdest dream you’ve ever had?
  2. What’s the worst lie you’ve ever told someone to get them in bed?
  3. What’s your biggest pet peeve?
  4. What’s the craziest thing you’ve done and gotten away with?
  5. What laws have you broken, if any?
  6. A zombie apocalypse is breaking out, who would you want to be trapped with?
  7. What’s a bad habit you have and want to break?
  8. Who’s the worst person you’ve ever kissed?
  9. What’s your craziest hookup story?
  10. Who’s a celebrity you find attractive that most people don’t think of?
  11. What’s the craziest thing you’ve done while under the influence?
  12. What’s an irrational fear you have and can’t get rid of?
  13. If you had to be stuck in a cartoon, which would you want to be stuck in?
  14. If you had to be any condiment, which would it be and why?
  15. What’s the cringiest trend you’ve ever participated in?
  16. What’s the strangest food you’ve eaten that you ended up in love with?
  17. What’s the craziest pick-up line you’ve used or had used on you?
  18. Have you ever hooked up with someone you’ve met off social media?
  19. What’s the craziest lie you’ve ever told to get out of work or another commitment?
  20. What’s the worst interview you’ve ever had?
  21. Where’s the weirdest place you’ve ever hooked up with someone?

21 Questions for Couples

Playing 21 Questions is a great way to spice up your date night or connect with a long-distance partner. Create a good mix with a deep question, funny question, and some intimate questions to get to know your guy or girl on a deeper level and have some fun while doing it! Browse the list below to find a perfect question or two to ask your partner while playing the game.

  1. What color underwear are you wearing right now?
  2. What’s something that turns you on a lot that you don’t often talk about?
  3. What’s your biggest fear?
  4. What’s your favorite type of music to listen to?
  5. What was your favorite sport to play when you were a kid?
  6. Do you want to have children one day?
  7. Do you believe in love at first sight?
  8. What’s your favorite way to have sex?
  9. What’s a bad habit I have that drives you nuts?
  10. What’s the biggest regret you have in life and would you go back to change it if you could?
  11. The zombie apocalypse is coming, where do you go to hide out?
  12. What’s your favorite thing about me?
  13. What celebrity do you find extremely attractive?
  14. What do you think is the sexiest feature on me?
  15. How many times have you been in love?
  16. When did you know that you were in love with me?
  17. What does your dream job look like to you?
  18. In your opinion, what’s the best date we’ve ever been on?
  19. What’s something you want to try in bed that you’ve never told me about?
  20. What’s a new hobby we could try together as a couple?
  21. What’s your favorite thing about our relationship?
About the author
Katee is a lover of language and is in awe of the power it holds. Read more articles from Katee on Thought Catalog.

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