21 Questions Game: How to Play and 330+ Questions to Ask

By Katee Fletcher Updated December 21, 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!

Classic

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 ask 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!

Ricochet

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 both people answer the question, 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 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 for playing 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!

What’s your favorite food to eat?
What’s your dream job?
How old were you when you had your first kiss?
What’s your favorite color?
What’s a pet peeve you have that you don’t tell anyone about?
What’s your favorite season of all time that you could live in for the rest of your life?
What’s your favorite movie of all time that you couldn’t live without?
What do you look for in a partner?
What’s the longest romantic relationship you’ve ever had?
What’s been your least favorite job thus far?
If you could only pick three artists to listen to forever, who would they be?
What’s the best piece of advice your parents ever gave you?
What would your dream date look like?
Who is your favorite character in… (pick a TV show or movie they like)?
What was your favorite subject in school?
What’s something crazy or adventurous you’ve done that you would do again in a heartbeat?
A flirty question could be, “What color underwear are you wearing right now?”
What’s the awkwardest date you’ve ever been on?
What’s a special talent you have that you don’t share much?
Who are you closest to in your family?
If you could change one thing about the world, what would it be and why?
What’s your zodiac sign?
Do you believe in soulmates?
How many times have you broken up with someone?
What is your type?
At what age are you hoping to get married?
Would you rather be considered attractive or intelligent?
Aside from love, what do you think is the most important quality in a relationship?
What’s something about your past that you’ve never told anyone?
Do you consider yourself an introvert or an extrovert?
Do you prefer cats or dogs?
What was your best vacation of all time?
Are you closer to your mother or your father?
What movie makes you laugh harder than any others?
Have you ever seen a ghost?
What is your biggest regret in life?
Do you believe in karma? Do you have an example of it happening?
If you could travel anywhere in the world, where would you go?
What animal do you have the most traits in common with?
What is your favorite book of all time?
What is your go-to karaoke song?
What was the last television show you binge-watched?
What genre of music could you live without?
What is your biggest dealbreaker when it comes to love?
What is your biggest turn-on when it comes to the opposite sex?
Do you believe in fate?
What is your favorite holiday to celebrate?
Have you ever had a near-death experience?
What website do you spend the most time on every day?
What is the best compliment you’ve ever received?
What celebrity do people tell you that you look like often?
What is your biggest fear in life?
When was the last time you cried, and why?
Do you consider yourself an emotional person or a logical person?
What was the last craft you worked on?
Are you a good driver?
Do you consider yourself attractive?
What is your biggest insecurity when it comes to your looks?
Which friend do you keep in touch with the most?
Which celebrity death had the biggest impact on you?
Do you have any tattoos?
What do you wish you could change about your personality?
What is your biggest accomplishment so far?
Do you care whether your parents get along with the person you’re dating?
Have you ever been in a car accident?
How many countries have you visited?
If you had to choose, do you prefer cooking or cleaning?
What is your favorite Disney movie?
What kind of student were you in high school?
What do you spend way too much money on?
What popular television show do you secretly hate?
What is your most impressive party trick?
When you’re angry, how do you calm yourself down?
Do you prefer the cold or the heat?
What do you think the meaning of life is?
Is double texting a big deal?
Who was your first kiss with?
Do you believe in astrology?
What’s your astrological sign?
What do you find to be the most attractive physical quality in another person?
What do you find to be the most attractive personality quality in another person?
Do you think you’re a good kisser?
Do you fall for someone fast or slow?
How did your last relationship end?
How old were you when you started dating?
Have you ever cheated on someone before?
Have you ever been cheated on?
How many people have you kissed?

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.

What’s the weirdest dream you’ve ever had?
What’s the worst lie you’ve ever told someone to get them in bed?
What’s your biggest pet peeve?
What’s the craziest thing you’ve done and gotten away with?
What laws have you broken, if any?
A zombie apocalypse is breaking out; who would you want to be trapped with?
What’s a bad habit you have and want to break?
Who’s the worst person you’ve ever kissed?
What’s your craziest hookup story?
Who’s a celebrity you find attractive that most people don’t think of?
What’s the craziest thing you’ve done while under the influence?
What’s an irrational fear you have and can’t get rid of?
If you had to be stuck in a cartoon, which would you want to be stuck in?
If you had to be any condiment, which would it be and why?
What’s the cringiest trend you’ve ever participated in?
What’s the strangest food you’ve eaten that you ended up in love with?
What’s the craziest pick-up line you’ve used or had used on you?
Have you ever hooked up with someone you’ve met off social media?
What’s the craziest lie you’ve ever told to get out of work or another commitment?
What’s the worst interview you’ve ever had?
Where’s the weirdest place you’ve ever hooked up with someone?
Do you believe in aliens? What do you think they look like?
What is the best pickup line you can come up with off the top of your head?
What is the weirdest thing about your family?
What funny movie do you quote the most?
Which Disney princess could you beat in a fight?
What is the least attractive name?
Are there any weird conspiracies you believe might be true?
What is the funniest wi-fi name you’ve ever seen?
Do you consider a hotdog a sandwich?
What is the funniest dad joke you’ve ever heard?
If you could talk to animals, which would be the meanest?
Where is the weirdest place you’ve used as a bathroom?
What is the weirdest website you’ve ever been on?
What is the strangest type of porn you’ve ever watched?
What is the most embarrassing thing you’ve ever done to impress a boy/girl?
If you could be any mythical creature, what would you be?
What is your silliest nickname, and what’s the backstory?
If you could make a serious movie into a musical, which one would you pick?
Which evil Disney character had a good point?
What’s the creepiest thing you could say to someone in an elevator?
Who is your favorite comedian — and what is their best joke?
If you could trade lives with an anime character, who would you choose?
How far would you make it in the Hunger Games?
What do you think you’re most likely to get arrested for doing?
If you had a clone, would you love it or hate it?
What television character would be annoying AF in real life?
What funny saying would you want to be written on your tombstone?
Have you ever set the kitchen on fire?
If you could invent a new sport, how would it be played?
What game show do you think you would actually win money on?
If you were an actual fly on the wall, who would you spy on?
What is the most annoying song ever written?
What color makes you want to puke?
What is the most inappropriate sounding word that isn’t actually dirty?
What’s the weirdest thing you’ve ever put in your mouth?
What holiday do you think we should cancel?
Would you rather give up pizza or sex?
Have you ever sexted the wrong person on accident?
What useless superpower would you want?
What is the craziest dare you’ve ever done?
Have you ever made a prank phone call?
Do you think Superman or Batman would win in a fight?
If you could kill off any cartoon character, who would it be?
If you could force everyone in the world to follow one rule, what would it be?
If you were a pair of shoes, what type would you be?
How much would you pay someone threatening to release your browser history?
How useful would you actually be in a zombie apocalypse?
What song would you want playing in the background during a fistfight?
If you started a cult, what would it revolve around?
How would you sum up the internet in one word?
If you could combine two animals to make a new creature, what would you make?
What would you love to hear a pet parrot say to you?
What is your favorite curse word to scream?
Would you rather eat worms or spiders?

Interesting 21 Questions for Friends

If your life was made into a movie, what would it be called?
What’s your dream concert to attend?
What’s a talent you wish you had?
If you had to be a dog, which dog breed would you choose to be?
Do you shower in the morning or at night?
Have you ever not tipped a waiter/waitress after going out to eat?
What’s your spirit animal?
If you could rename yourself, which name would you pick?
If you could be any superhero, who would you be?
If you could be any supervillain, who would you be?
If you owned a time machine and could only choose to go back in time or go into the future, which would you pick?
If you were forced to only listen to one song for the rest of your life, which song would it be?
What’s the worst lie you’ve ever told your parents?
In the movie of your life, which actor/actress would you want to star as you?
Do you consider yourself a morning person or a night owl?
If you could live anywhere in the world, where would it be?
What’s the biggest life lesson you’ve learned thus far?
What was your favorite game to play growing up?
If you could vacation anywhere in the world, where would you go?
What song do you currently relate to the most?
Would you rather have endless money or incredible fame?
If you had the option, would you change something about your appearance? What would it be?
If you had to choose a celebrity to be your children’s mother/father, who would you choose?
If you found a briefcase of money on the street, would you keep it?
What’s your favorite part of the day?
What’s the last book you read and really enjoyed?
When was the last time you stepped out of your comfort zone?
What never fails to get you angry?
What’s a guilty pleasure of yours?
What’s more important, truth, or happiness?
Do you prefer planning or spontaneity?
What’s one habit you find totally repulsive?
What’s something you’re eternally grateful for?
What’s your favorite smell?
What’s the weirdest way you’ve become friends with someone?
What’s the strangest thing you’ve done out of boredom?
When you were a child, what appeared to be the best part of being a grown-up?
What’s been one of your happiest memories in life?
What’s the worst piece of advice you’ve ever taken?
If you knew you would die in a year, what would you change about how you live?
What was your favorite childhood TV show?
What are the top three things on your bucket list?
How did you and your best friend meet?
What are your thoughts on marriage?

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.

What color underwear are you wearing right now?
What’s something that turns you on a lot that you don’t often talk about?
What’s your biggest fear?
What’s your favorite type of music to listen to?
What was your favorite sport to play when you were a kid?
Do you want to have children one day?
Do you believe in love at first sight?
What’s your favorite way to have sex?
What’s a bad habit I have that drives you nuts?
What’s the biggest regret you have in life, and would you go back to change it if you could?
The zombie apocalypse is coming; where do you go to hideout?
What’s your favorite thing about me?
What celebrity do you find extremely attractive?
What do you think is the sexiest feature on me?
How many times have you been in love?
When did you know that you were in love with me?
What does your dream job look like to you?
In your opinion, what’s the best date we’ve ever been on?
What’s something you want to try in bed that you’ve never told me about?
What’s a new hobby we could try together as a couple?
How many people have you slept with?
What’s your favorite thing about our relationship?
What is your ideal number of times to have sex each week?
Would you rather have me turn out more like my mother or father?
What television couple reminds you of us?
What song makes you think of me?
What’s your dream house look like?
Have you ever had a naughty dream about me?
What is your love language?
Which one of my friends do you get along with the best?
Did you ever come close to breaking up with me?
When did you know I was the one?
If we could travel anywhere in the world together, where would you want to go?
What is your ideal number of dogs? Cats?
What is my worst physical feature?
Where do you want to be living in ten years?
When you were younger, did you picture yourself getting married?
Who was your first crush?
What makes me different from the other people you’ve dated in the past?
What movie sex scene have you rewatched a million times?
What’s your favorite time of day to have sex?
When was the last time I made you jealous?
Do you think I’m out of your league?
How often do you touch yourself?
How long do you think a couple should wait before having kids?
What values do you want to instill in your children?
What was your most romantic date — with me or anyone else?
How old were you when you lost your virginity?
What couple’s karaoke song do you like the best?
What is the most romantic gesture you’ve ever received?
What would you like to change about our relationship, if anything?
Do you believe communication or trust is more important?
Who were your relationship role models growing up?
Which celebrity couple do you think is the cutest?
What is your idea of a healthy relationship?
What do you miss the most about being single?
What advice would you give your younger, single self?
What is one word you would use to describe our relationship?
What do you wish we did more often?
What milestone are you most excited about reaching with me?
Do your relatives approve of me?
What is the most memorable compliment I’ve given you?
Which chore do you wish I would do instead of you?
What is your favorite thing about our house?
What year of our relationship was the hardest?
What year of our relationship was the greatest?
What is your biggest relationship fear?
Do you have any baggage from past relationships?
Which romantic comedy is your favorite?
What is the best relationship advice you’ve ever received?
Have you ever had a crush on a cartoon character?
Do you have a high sex drive?
Do you think you’ll make a good parent?
What is the worst mistake new parents can make?
Does love scare you?
Would you rather give up hugging or give up kissing?
Who is your dream partner?
If you could relive our first date, what would you do differently?
If you had to do the same thing every night together, what would it be?
Which celebrity couple looks the most like us?
Which celebrity couple looks the least like us?
What type of couple do you want us to be?
What does our communication look like?
How are we different from other couples?
What makes us special and unique?
What’s one word that would describe our love?
What’s one phrase that would describe our love?

21 Questions for Girlfriends

What color bra are you wearing right now?
What’s your favorite quality about me?
What’s your favorite thing that we do together?
What quality would you improve about me?
What feature is your favorite of mine?
How would you define our love?
When do you want to get married?
Where do you want to get married?
What song do you want to play at our wedding?
Who inspires you the most?

21 Questions for Boyfriends

What color bra is your favorite of mine?
What features do you love most about me?
What would you improve about me if you could improve anything at all?
What’s our favorite song?
What makes you think of me?
Who inspires you the most?
What’s your favorite thing for us to do together?
Do you want to go to a beach or the mountains?
What was your childhood like?
What would you do for work, if you could do anything at all?

Dirty 21 Questions for Couples

There’s no better way to spice up your relationship than a naughty game of 21 questions. End a date night with these dirty questions and find out each other’s secret thoughts and fantasies.