21 Questions Game

The 21 questions game is quite simple. Its name largely implies its rules. The questions themselves may not be considered a game so much as a bonding exercise that can also be fun, if you ask the right questions. This is why the goal of these 21 questions should focus on deep and meaningful conversation.

The great thing about the game is that you can play it with just about anyone and simply modify how deeply the 21 questions that you ask go, based on your audience. You can play it with just one other person or as a big group of friends. The different ways to approach it are nearly endless.

The entire goal is promoting understanding, cooperation and empathy. It does this by making sharing and self-disclosure more structured and inherently reciprocal, due to its back-and-forth dynamic.   

By exploring these questions and being mutually vulnerable in your answers, you can create a powerful bonding moment. One where common ground is found within compatible outlooks and ways of thinking, rather than through common experiences, which is a lot more emotionally material. Through the inbuilt sharing aspect of the 21 questions game, you naturally develop trust, not just through disclosing in your answers but also in how positively you receive them.

As these questions can often speak to more meaningful topics, playing this game with someone you’re trying to get to know better will eventually create a shared moment based on intimacy and mutual respect. Let’s look at some examples of questions you could include in your game.  

21 questions game to get to know someone

Even though these questions can often venture into deeper territory, it’s generally more entertaining with new friends and casual acquaintances. People whom you don’t already know very well. The game structure of the questions and the fact that everyone has the answer promotes a warm, more trusting atmosphere where people can feel more comfortable being open. 

Finding the right 21 questions to get to know someone is all about personalizing them to whoever you plan on playing with. To really get to know someone, you should include questions that speak to a range of different aspects. This can include personal facts, past experiences, viewpoints on certain issues, their personal tastes or even something random. It’s best to introduce this game during a more extended interaction. It shouldn’t form the whole reason you decided to meet up but rather as something that can enrich conversation, get people more engaged and create a feeling of intimacy that naturally flows into the rest of the interaction.

Here’s a list of 21 questions to try out:

1. What’s a small thing that always brightens your day?
2. If you could live anywhere for a year, where would it be?
3. What’s a random skill you’d love to master?
4. What’s one thing you wish people asked you more often?
5. Who’s someone that’s had a big influence on who you are?
6. What’s a hobby that makes you lose track of time?
7. If you could go back to any age, which would you choose and why?
8. What’s your favorite way to start your mornings?
9. What’s a movie or book that changed your perspective on life?
10. What’s a goal you’re currently excited about?
11. If you could instantly become fluent in another language, which one?
12. What’s something that always makes you laugh, no matter how often you hear it?
13. What’s one thing you’ve done recently that you’re proud of?
14. If you could meet your younger self, what advice would you give them?
15. What’s something you love about your current stage in life?
16. What’s a simple pleasure you enjoy daily?
17. Who do you talk to when you need perspective on life?
18. What’s your favorite childhood memory?
19. What’s a hidden talent that surprises people?
20. If you could trade jobs for a week with anyone, who would it be?
21. What’s the kindest thing someone’s ever done for you?

21 questions game to ask a guy

You may think that we’d suggest including questions that speak to classic masculine ideals and interests. But in the 21 questions game, it’s often a better idea to go in the complete opposite direction and focus on more emotional questions. A study from the University of Amsterdam found that while many men have very progressive views towards emotional expression and vulnerability – reflecting evolving modern gender norms – they largely fail to find this quality within themselves and their lives.¹

This indicates that men often want to discuss their emotions and topics that require vulnerability – as long as it’s reasonably positive – but often lack the social toolset to approach this topic with the same ease and insight as women. Gamifying the act of vulnerability with a well-crafted list of 21 questions to ask a guy may provide the structured emotional outlet he’s been quietly looking for.

If you’re unsure, text the guy beforehand, explaining the game and that you’d like to play it next time you meet up or interact. Here’s a good list of questions personalized to men’s styles of processing emotions.

1. What’s your idea of a great weekend?
2. What motivates you the most right now?
3. What’s your favorite thing to do when you need to unwind?
4. If you could learn one new skill instantly, what would it be?
5. What’s something you’ve always wanted to try but haven’t yet?
6. What’s a funny or embarrassing story from your childhood?
7. Do you prefer adventures or chill nights at home?
8. What’s your biggest pet peeve?
9. What’s something that instantly makes you laugh?
10. If you could live in any era, which would you choose?
11. What’s a piece of advice you still live by?
12. Who’s your biggest inspiration?
13. What’s a goal you’re currently working toward?
14. What’s one thing that always makes a relationship stronger?
15. If you could relive one year of your life, which one would it be?
16. What’s something you find attractive in a partner that isn’t physical?
17. What’s the most spontaneous thing you’ve ever done?
18. What’s a movie you could watch 100 times and never get tired of?
19. What’s something people misunderstand about you?
20. What’s your favorite memory with friends?
21. If you had to describe yourself in three words, what would they be?

21 questions game to ask a girl

Conversely, a study from the Journal of Experimental Social Psychology found that women are more comfortable with sharing and self-disclosing personal information with people, including negative information.²

If you have romantic feelings for the woman you want to play the 21 questions game with, then you can use it as an opportunity to explore her views on dating, personal attraction or even how she sees you – as long as you make it somewhat subtle. Remember that you have to answer the same question, so don’t ask anything you’re not comfortable sharing.

Women are more likely to be open to playing this game. However, it’s still a good idea to introduce the idea during an interaction where you know you’ll both have time to answer all 21 questions.

Here’s a question list you can use or simply draw inspiration from: 

1. What’s your idea of the perfect date?
2. What kind of adventures do you dream about having?
3. What’s something you’re proud of accomplishing recently?
4. What’s a compliment that always makes you smile?
5. What’s your favorite kind of humor?
6. What’s a random passion or interest you could talk about forever?
7. What’s your favorite season, and why?
8. If you could design your ideal day from start to finish, what would it include?
9. What’s a movie or show you could quote word-for-word?
10. What’s your favorite way to spend time with people you love?
11. What’s a song that instantly improves your mood?
12. What’s the nicest thing anyone has said to you?
13. If you could master any creative hobby, what would it be?
14. What’s something people would be surprised to learn about you?
15. What’s your favorite comfort meal?
16. If you could plan your dream trip, where would you go?
17. What’s your most relatable ‘oops’ story?
18. What’s your favorite way to recharge after a long week?
19. What makes you feel most confident?
20. What’s something that makes you laugh every time you think about it?
21. What’s your favorite scent or small sensory joy?

A good set of 21 questions explores a variety of topics, including people’s deeper emotions, the small frivolities in life that make our day and interesting scenarios that let their imagination take flight. It’s essential to remember that while this is a great tool for bonding, it works best when there are questions that are entertaining and evoke unexpected answers. After all, it is a game.

A sound approach to the 21 questions game involves preparation. If the questions haven’t been predetermined, which is one of the ways to play the game, then try to plan more questions than you need. Have some questions as backup in case a certain line of questioning makes some people reticent or uncomfortable. This way, you can change the topic and quickly pivot away from personal questions towards more emotionally neutral ones.

A good game of 21 questions is also about introducing it at the right time. Try to pick a moment in the conversation when there’s a generally positive tone, but the energy of the interaction has died down a bit, leaving a natural, open opportunity to introduce the game to them. 

1. What’s something you wish more people understood about you?
2. What’s a lesson life has taught you in the past year?
3. What’s a moment that always makes you nostalgic?
4. What’s a talent or hobby you’d love to spend more time on?
5. What’s your go-to way to have fun with friends?
6. What motivates you on days you feel unproductive?
7. Who’s someone you admire for their outlook on life?
8. What’s your favorite way to spend a rainy afternoon?
9. What’s one thing that can instantly turn your bad day around?
10. What’s a small luxury you think everyone should enjoy?
11. What’s a piece of advice you’d give someone younger than you?
12. What’s something you recently learned that fascinated you?
13. What’s your proudest achievement so far?
14. If you could relive one moment just for fun, what would it be?
15. What’s the best trip you’ve ever taken?
16. What’s your current favorite show, movie, or book?
17. What do you think makes a great friendship last?
18. What’s your favorite weekend activity?
19. What’s a habit that always helps you feel centered?
20. What’s something you’re curious about exploring this year?
21. What’s your personal definition of success?

21 questions to ask your crush

It’s perfectly understandable to feel nervous about the idea of playing the 21 questions game with someone you like. One study found that most people unconsciously display large clusters of anxiety-related physiological and behavioral reactions around someone they’re attracted to. However, it was also found that these reactions are perceived positively as signals of interest and attraction.³

Formulating an engaging list of 21 questions to ask your crush can help ease these nerves by making the interactions more structured and predictable while remaining meaningful and gently expressing your feelings. It gives you the ideal opportunity to explore different romantic aspects like how they approach dating, their notions of intimacy and the things that occupy their free time.   

Like with anyone, the best approach to this involves timing. You want to pick a moment that feels organic but that also tells your partner that you want to play this game with them, specifically, because you want to know them on a deeper level.

Here are 21 questions to help you with your list:  

1. What’s your go-to way to make someone smile?
2. What’s something that makes you instantly attracted to someone?
3. What’s your ideal first date vibe?
4. What’s a small gesture that means a lot to you?
5. What’s the best compliment you’ve ever received?
6. What’s something you’d love to do with a future partner?
7. What’s your favorite way to spend a lazy weekend?
8. What’s a song that describes your current mood?
9. What’s your favorite quality in a person you’re dating?
10. What’s something you find charming about people?
11. Do you believe love happens by chance or through effort?
12. What’s your favorite memory from a past date or relationship?
13. What kind of humor instantly wins you over?
14. What’s a dream vacation you’d love to share with someone?
15. What’s a random turn-on that most people wouldn’t expect?
16. What’s your biggest deal breaker in dating?
17. What makes someone unforgettable to you?
18. What’s your favorite romantic movie or show?
19. What’s a goal you’d love to achieve with someone you love?
20. What’s the cutest thing someone’s ever done for you?
21. What’s your go-to comfort snack for a chill date night?

Flirty 21 questions to ask

Using the 21 questions game to flirt or convey your feelings is a useful way to broach the topic of dating or your attraction, in a way that feels more subtle and doesn’t put them on the spot as much. It can be a handy way to introduce flirting into your dynamic with someone new or to tell someone in your life that you’ve started to see them differently.

This shouldn’t be surreptitious, though. Ideally, the other person should pick up on the fact that you’re flirting with them. Flirting signals are generally how people softly test each other’s perspective on romance and begin to gently move the interaction towards dating at some point. What is important is reading how they react to your flirting, both in tone and non-verbal cues. 

You may be wondering, “What are some flirty 21 questions?” We included some examples below, but we’d also suggest coming up with alternative questions so that you can pivot if the flirting isn’t reciprocated or makes them feel uncomfortable.

1. What’s the most charming thing someone can do to catch your attention?
2. What’s your favorite way to be flirted with?
3. What’s a compliment that never gets old for you?
4. What’s something you find irresistibly attractive in a person?
5. If we were at a party, how would you flirt with me without saying a word?
6. What’s your go-to flirty move?
7. What’s a moment when someone made your heart skip a beat?
8. What’s your favorite song to dance to with someone special?
9. What’s the most romantic place you’ve ever been?
10. What’s something you think makes a date unforgettable?
11. What’s a physical feature you find impossible to ignore?
12. What’s the most subtle way to tell someone you like them?
13. What’s your favorite way to spend a cozy night in?
14. What’s a playful question you’ve always wanted to ask someone you like?
15. What’s a scent that drives you crazy—in a good way?
16. What’s your favorite form of affection?
17. What’s something you find surprisingly sexy about confidence?
18. What’s the boldest thing you’ve done to show interest in someone?
19. What’s your favorite kind of slow dance moment?
20. What makes a flirtation go from fun to unforgettable?
21. What’s your favorite kind of compliment to receive from someone you like?

Juicy 21 questions to ask

Juicy 21 questions are more unabashed and intimate. They ask the other person for the unfiltered truth and other juicy personal titbits. This doesn’t mean that they should be inappropriate but rather seek a much deeper understanding of the person you’re talking to. For this reason, they have the best effect when you use these 21 questions to ask someone you already have an established personal relationship with.

If you’re unfamiliar with this type of question, you may be thinking, “What are some juicy 21 questions?” Here are some examples that you can use to guide how personal you should go in your approach.

1. What’s your most memorable kiss?
2. What’s the boldest thing you’ve ever done for love?
3. What’s something you’ve always wanted to try but haven’t yet?
4. What’s your biggest guilty pleasure?
5. What’s your favorite romantic memory?
6. Who was your first crush, and what made you like them?
7. What’s the most romantic gesture you’ve ever received?
8. What’s something about relationships that turns you on instantly?
9. What’s the most spontaneous thing you’ve done with someone?
10. What’s a secret fantasy you’re comfortable sharing?
11. What’s your favorite kind of affection—hugs, kisses, or words?
12. What’s the best date you’ve ever been on?
13. What’s a random turn-on that catches you off guard?
14. What’s something that makes someone instantly attractive to you?
15. What’s a fun way to keep the spark alive in relationships?
16. What’s a flirty compliment that always makes you blush?
17. What’s the best part about falling in love?
18. What’s one word that describes your dating style?
19. What’s a song that gives you butterflies?
20. What’s your favorite type of foreplay: emotional, mental, or physical?
21. What’s the first thing you notice when you like someone?

Sexy 21 questions to ask

These 21 questions turn up the heat, speaking overtly to sexuality and physical connection. While it may be best to avoid being too lewd, there’s no mistaking the intent of these questions. It’s almost impossible to mask your intentions when you ask these questions.

This version of the 21 questions game could even be described as a form of emotional foreplay. This is why it’s generally best played with someone you have an intimate relationship with. However, it’s not just about the sexual tension these questions generate. The answers themselves can help you understand a partner’s desires better, their unspoken fantasies and how to be more attentive to their physical needs. And because these 21 questions go both ways, so do the insights.

Try playing this game during the middle to later stages of your next date night or in a conversation where it already feels like there’s strong chemistry.. Use their tone and body language to judge how spicy to make your follow-ups. If you’re feeling a bit stuck, you can always use this list of questions.

1. What does “sexiness” mean to you—playful, bold, mysterious, or something else entirely?
2. What kind of flirtation flips a normal night into a memorable one for you?
3. What’s a classy, subtle way someone has turned you on without saying much?
4. What slow-burn kind of intimacy do you find irresistible?
5. What’s a fantasy vibe (setting, music, energy) that you’d love to explore one day?
6. What’s a piece of clothing that makes you feel confident?
7. What kind of roleplay or scenario could be fun, as long as there’s trust and consent?
8. What’s a boundary you honor that actually makes things sexier?
9. What’s a spontaneous moment that made sparks fly for you before?
10. What song would you queue first if you were setting the mood?
11. What’s a non-obvious turn-on that most people overlook?
12. What’s your favorite way to build anticipation—words, looks, or actions?
13. What’s a bold flirt you’ve always wanted to try but haven’t yet?
14. What kind of compliments make you feel deliciously seen?
15. What’s a power dynamic (playful, equal, alternating) that feels exciting to you?
16. What’s the best thing a partner can do with their hands?
17. What’s your favorite kind of after-the-date chemistry—slow cuddles, midnight snack, late-night drive?
18. What playful truth-or-dare prompt would you actually want someone to give you?
19. What makes you feel safe enough to be adventurous?
20. What’s your favorite way to tease—words, timing?
21. What’s one sexual fantasy you’d love to co-create with the right person?

Interesting 21 questions to ask

Interesting questions in the game are designed to be thought-provoking, engaging people’s intellect and sense of curiosity. This is a great way to introduce a more entertaining energy to the game, to give the other person a break from self-disclosure. These instead focus on what it is about their thoughts and experiences that make them unique.

The right 21 interesting questions to ask can vary depending on the participants’ personalities. It’s best to prepare a broad range of different kinds of interesting questions so that you can steer toward more engaging topics if your line of questioning starts to evoke unenthusiastic responses. The most reliably interesting topic to most people is themself. A study from Harvard University found that people spend 30-40% of conversations talking about themselves and that we find self-disclosure a pleasurable experience on a neurological level.⁴ So, the science is there. All you need are the questions. Try out some of these examples to add to your list. 

1. What contradiction about yourself actually makes perfect sense once people know you?
2. What’s a curiosity you’ve chased that changed how you see the world?
3. If a museum featured your life, what would the three exhibits be called?
4. What’s a belief you outgrew—and what replaced it?
5. What’s the most meaningful risk you’ve taken that paid off in an unexpected way?
6. What question do you wish people asked you more often?
7. If you could master one obscure skill just for joy, what would it be?
8. What’s a moment you felt completely in your element?
9. What strange coincidence still gives you chills (in a good way)?
10. If you could time-capsule one present-day piece of yourself, what would you choose?
11. What book, film, or song made you rethink a habit or value?
12. What small, daily ritual feels like a secret superpower?
13. If your future self wrote a note on a napkin to you today, what would it say?
14. What do you think people underestimate about love or friendship?
15. What’s a hill you’d jokingly die on that actually reveals something true about you?
16. If you could press “enhance” on one trait—curiosity, patience, courage—what would you pick and why?
17. What’s a memory that keeps teaching you new lessons as you get older?
18. If you could borrow anyone’s brain for a day, whose—and what would you try to understand?
19. What’s a decision you made that looked odd from the outside but felt right inside?
20. What question would you ask an all-knowing librarian about your life?
21. What’s something you hope never stops surprising you?

Deep 21 questions to ask

Deep questions are like interesting questions in the game except that they have an intrinsic emotional component that touches on people’s inner selves and the feelings that underlie their beliefs. These questions can cover a range of topics, including their values, personal philosophies, the experiences that shaped them or their outlook on people and relationships.

While you can research the right 21 deep questions to ask the person you’re playing with, the best ones should come from the heart and should be based on what you already know about the other person. Because deep questions tend to be less emotional, many ignore them as an aspect of intimacy. But it’s been shown that exchanging deeply can have a profound impact on how we perceive the quality of interactions.⁵

1. What’s a decision that changed your life forever?
2. What’s something you believe most people don’t understand about you?
3. What does true happiness mean to you?
4. What’s your biggest fear when it comes to love?
5. How do you usually deal with disappointment?
6. What’s something you’ve forgiven yourself for recently?
7. What’s your idea of real emotional intimacy?
8. Do you think people can fall in love more than once?
9. What makes you feel truly at peace?
10. What’s one lesson you learned from heartbreak?
11. Do you believe people can change for love?
12. What’s a core value you’ll never compromise on?
13. What’s the most vulnerable thing you’ve ever shared with someone?
14. What’s your biggest dream in life?
15. What does self-love look like for you?
16. How do you know when you truly trust someone?
17. What’s something you’re afraid of losing?
18. What’s one mistake that taught you something powerful?
19. Do you think love is more about feeling or commitment?
20. What’s something you hope never changes about you?
21. What’s your definition of emotional maturity?

21 questions game for couples

While the game is perfect for budding romantic connections and new friendships, the game’s original use was as a bonding exercise for couples. Structured relationship questions, like the 21 questions game, allow you to approach difficult topics from a more positive angle.

Your partner is always growing, and your relationship dynamic is in constant flux. This shouldn’t be a source of concern because this constant evolution is how you can still create new experiences and share different dimensions of yourself even after years of being in a loving and intimate relationship.

When it comes to 21 questions for couples, it’s best to give your partner some forewarning before the game rather than surprising them. You may even want to consider constructing the list of questions together, so that they satisfy both your desired talking points in the relationship. You can use some of the examples in this list to help inform and guide your 21 questions.

1. What’s one thing that made you fall for me?
2. What’s a small gesture I do that always makes you smile?
3. What’s one thing we’ve done together that you’ll never forget?
4. What’s your favorite date we’ve ever had?
5. What’s something new you’d like to try as a couple?
6. How do you think we’ve grown since we first met?
7. What’s a funny memory we’ll always laugh about?
8. What’s your favorite thing about our relationship dynamic?
9. If we could relive one day together, which would it be?
10. What’s your favorite inside joke we share?
11. What do you think makes our connection special?
12. What’s a goal we could set together this year?
13. How do you like to be comforted when you’re upset?
14. What’s a dream vacation you’d love to take with me?
15. What’s your favorite quality about me?
16. What’s something I do that makes you feel loved?
17. What do you think our strongest shared value is?
18. What’s your favorite cozy night-in activity with me?
19. If our love story were a movie, what would it be called?
20. What’s something about our relationship you’re proud of?
21. What’s a new memory you want us to create together soon?

21 questions to ask your boyfriend

While we’ve explored the best way to approach guys with the game, it’s a bit different when you’re asking men questions in relationships. A study in the Journal of Family Psychology found that men specifically strongly link their sense of well-being and support to the health of their relationship.⁶ This doesn’t indicate a mismatch in affection or love but rather that men tend to emotionally rely on their partners more than women.

The problem is that people often try not to cast themselves in a negative light when they like someone, which leads to emotional accumulation. Coming up with 21 questions to ask the guy you’re dating provides structured catharsis. It allows you to be present for your boyfriend without becoming an emotional crutch for his problems, which can lead to an enabling relationship that can sabotage any self-care efforts.

Your 21 questions should be personalized to your boyfriend, but you can use these questions to help get you started and guide your list of questions.

1. What’s your favorite memory of us so far?
2. What do you think makes our relationship work so well?
3. What’s one goal you want us to accomplish together?
4. What’s something I do that always makes you laugh?
5. What’s a small gesture that means a lot to you?
6. What’s your favorite way for us to spend quality time together?
7. What’s one thing you think we should do more often?
8. How do you know when you’re truly happy in a relationship?
9. What’s something new you’d love for us to experience?
10. If you could describe our connection in one word, what would it be?
11. What’s your favorite compliment I’ve ever given you?
12. What’s a dream trip you’d love to take with me?
13. What’s your favorite inside joke between us?
14. What’s a small thing you’ve noticed about me recently?
15. What’s one thing you love about how we communicate?
16. What do you think makes our bond unique?
17. What’s your love language?
18. What’s one piece of advice you’d give to someone about relationships?
19. What’s something I do that surprises you in a good way?
20. What’s a silly memory of ours you’ll never forget?
21. What’s one thing you’re grateful for in our relationship?

21 questions to ask your girlfriend

By introducing the 21 questions game into your dynamic, you’re not only showing your willingness to be a distinctly dependable part of her emotional network, you’re also giving her permission to be open with you instead of putting on a happy face for the sake of harmony in the relationship. This authenticity with each other naturally creates a deeper sense of intimacy.

There’s never a bad time to try to get to know your girlfriend on a more meaningful level. You could even say an exercise like this is essential to growing the relationship. It can even be a tool for conflict resolution. Here are some questions you can try to mix in with your list of more personalized questions.

1. What’s your favorite memory of us together?
2. What’s a new experience you’d love us to try?
3. What’s something small that always makes you happy?
4. What’s your favorite part about our relationship?
5. What’s something I do that makes you feel loved?
6. What’s a dream vacation you’d want to take with me?
7. What’s a tradition you’d love to start as a couple?
8. What’s something I do that makes you laugh every time?
9. If our relationship were a book, what would the title be?
10. What’s one thing I could do that would make your day better?
11. What’s your favorite way for us to spend weekends together?
12. What’s something about me that always surprises you?
13. What’s a romantic movie moment you secretly love?
14. What’s a goal we can set for our future?
15. What’s a small thing that reminds you of me?
16. What’s a song that always makes you think of us?
17. What’s one lesson our relationship has taught you?
18. What’s something new we should try together this month?
19. What’s your idea of a perfect date night?
20. What’s your favorite inside joke between us?
21. What’s one word that perfectly describes how you feel about us?

Firstly, this game has no relation to the popular conversation game, 20 Questions. 21 questions is a game that is loosely inspired by the 2003 hit single by 50 Cent, “21 Questions” – which also explored relationship dynamics. It later emerged as a growing trend in dating advice pieces and on social media.   It involves you and one or more people taking part in a structured form of deep enquiry, where every player takes a turn answering the same question. This taps into a concept known as gamification, where services use game elements to increase people’s engagement, motivation and level of emotional investment.⁷ It’s prominently employed in educational environments. 

By framing vulnerability and emotional exchange as an interactive exercise, you’re encouraging the other people playing to view the activity as being reward-based while lowering the social stakes.

Most importantly, you’re approaching it from a sincere, up-front direction that isn’t manipulative. It’s simply the obvious structure itself that makes it a more attractive and manageable concept.  

How to play the 21 question game?

While it has a fairly loose approach, the 21 questions game has rules that make it different from a regular conversation. But there isn’t a 21 questions official association, so feel free to see them as guidelines.

• The classic way to play is for every participant to take turns answering the same question until you get to 21.
• Alternatively, you can progress with each answer until you’ve collectively asked each other 21 questions, or you can each come up with your own list of questions.
• It can be played with one or more players, but too many may slow the conversational momentum of the game.
• People are allowed to decline answering, in which case you should move on to the next player or question.
• You and other players can declare restrictions on the topics of the questions that are asked.

If the questions have been predetermined, you should let other players see the list beforehand.

What are the ideal settings to play the 21 questions game?

You may be wondering about the best time to introduce this game, or which social situations suit it best.

• Meet-ups with new acquaintances – The 21 questions game is a great ice breaker and is a way to get a group that don’t know each other well to be on more even terms and enthusiastic about the interaction.
• At dinner parties – This is handy because you’re already all in one place and in the mental space for active socializing. 21 questions can help spark a more lively exchange or simply help guests get to know each other. 
• On a date – While we’d advise a more organic approach on first and second dates, this game can really save a date that isn’t quite clicking. It may not necessarily lead to another date, but it can at least make the one you’re on more enjoyable.
• Relationship discussions – Use this and other structured conversations as a way of checking in on the state of the relationship or as a more level-headed method of working through emerging sources of conflict.

Can you play the 21 questions game over text?

Yes, the 21 questions game is incredibly well-suited to a text messaging format. However, they elicit social benefits that are somewhat distinct from face-to-face interactions. You may not be able to accurately gauge chemistry, compatible communication styles or make use of non-verbal cues as effectively. But what you lose in one area you more than make up for in others, according to a recent study published in Heliyon.

This study found that over text, simply the act of trying to engage in a more meaningful conversation has a greater impact on feelings of closeness than the topic discussed or the content of the questions themselves.

Further, it was found that text exchanges offered a host of social benefits that generally relate to lower perceived social risk. This included aspects like structured turn-taking increases reciprocity and text has a positive effect on self-disclosure because people don’t have access to perceived negative cues. It also gives players more time to reflect on their answer and respond more thoughtfully.⁸

How to make the 21 questions game more fun?

Structured conversations like the 21 questions game are engaging but they can sometimes seem less spontaneous and versatile. This is just a bias created by the notion of structure. Here’s how to make it more entertaining.

• If their answer creates an interesting new line of conversation, don’t be afraid to temporarily abandon the pre-planned list for a question that feels more apt in the moment.
• Include other light game elements, like a set number of vetos, playful penalties for not answering or that you have to answer questions by describing a concept rather than using its name. However, we’d advise against using alcohol as a gaming component.
• Use humor to make the game feel more entertaining and less invasive.
• Adapt your question list based on what you know about the players to make it feel more personal.
• Ask questions about feelings instead of facts to make it more emotionally engaging.
• Don’t get too hung up on rules and structure if it starts veering off. Rather, focus on the energy it adds to the interaction. 

What are questions to avoid in the 21 questions game?

Just because it’s a game doesn’t mean it should be a free-for-all. The rules for polite conversation still apply. Here are topics to avoid in your question.

• Complex questions – Try to limit your question to 20 words or fewer and never ask more than one thing per question. The ideal 21 questions to ask should encourage active exchange, not confusion or pensive thought.
• Money – This applies to all conversations, including structured ones. Discussing money generally makes people uncomfortable for numerous reasons, so it’s better to have longer-form discussions around this topic
• Closed-ended questions – The game is supposed to spark conversation, so choosing questions that can be answered in just a couple of words works against that goal.  
• Politics and religion – These may play a significant role in how you judge compatibility, but they should be addressed early and in a different format.