If you find small talk tiresome, the 21 Questions game is a straightforward activity that eases the tension on first dates, in new friendships, or at work parties. It can also be employed to explore deeper aspects of your relationships with anyone in your life. Here is all you need to know about how to play the 21 Questions game, along with the best questions to ask for more engaging conversations.

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What is “21 Questions”?

“21 Questions” is a conversational game designed to initiate discussion by posing a series of questions to gain a deeper understanding of someone. Whether played online or in person, the game accommodates two individuals or larger groups. This straightforward activity showcases your interest in getting to know others while also providing an opportunity to share personal secrets.

Ideally, “21 Questions” sparks fresh conversation topics between you and the other participant(s). However, if you still find yourself grappling with awkward silences and small talk, you might consider incorporating some conversation hacks to maintain a smooth dialogue. Like learning to ride a bike, mastering the art of conversation is a skill that anyone can acquire.

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How to Play 21 Questions

Playing the 21 Questions Game is incredibly straightforward, with honesty being the primary rule. Whether with two or more participants, the game can be enjoyed in various settings. All you need is a set of situation-appropriate questions and a suitable place to gather while providing answers. You can even engage in the game through text!

There are several ways to play 21 Questions:

• Round and Round Questions: In the classic version of the game with a group, the first person selects a question, and then the group proceeds in a circle, with each person providing their answer. Optionally, participants can have one “skip” for a question they prefer not to answer.
• Ricochet Questions: Tailored for two participants, this version involves a back-and-forth approach. Person A poses a question, and Person B responds. Subsequently, Person B selects a different question, and Person A provides their answer. This format is ideal for a romantic date or a casual meetup, allowing ample time for discussion before moving on to the next question.
• Rapid Fire: Geared towards couples or friends seeking to delve into each other’s “raw” responses, a rapid-fire game entails posing 21 questions consecutively to one person. Once all questions are answered, roles switch, and the initial person responds to the same set of questions.

The key to a successful 21 Questions game lies in selecting appropriate questions for the context. While group settings may benefit from avoiding overly invasive or intimate topics, more intriguing questions could be employed to add spice to interactions with a significant other with whom you have an established rapport.

Here, we provide 21 Question ideas for:

• Getting to know someone
• A new relationship
• A new crush
• Flirty questions
• Texting a friend

110 Best Questions for the 21 Questions Game

Rather than resorting to mundane inquiries like “What’s your favorite color?” or “What do you do for a living?” these suggestions for the 21 Questions Game are designed to be thought-provoking and intriguing. Before diving into the game, take a moment to review the lists and ensure you are at ease both posing and answering each question. If any seem uncomfortable, feel free to omit them or create your own!

21 Questions to Get to Know Someone

These questions delve beyond the realms of work and hobbies, aiming to uncover more about how someone perceives the world. The list is inquisitive and occasionally philosophical without delving too deeply into personal territory.

1. If you could travel to any point back in time, what year would you choose and why?
2. What are a few things at the top of your bucket list?
3. What decision do you look back on and say, “What was I thinking?”
4. If you could give your 16-year-old self one piece of advice, what would it be? Would you have listened?
5. Who is/was the most influential person in your life?
6. What is the first thing you would do if you won the lottery?
7. What is the weirdest dream you’ve ever had?
8. If you could have any superpower, what would you choose and why?
9. What is the most embarrassing thing you’ve done in public?
10. Would you consider yourself adventurous, or do you play it on the safe side?
11. What is your go-to karaoke song?
12. What would you title this chapter of your life?
13. If you could re-live any part of your life so far, which part would you choose and why?
14. What is the biggest lesson you learned from your teens/twenties?
15. Who would you want to sit next to on a ten-hour flight across the world, and why?
16. If you could be any kind of dog, what breed would you be?
17. Do you think the convenience of the internet is worth the loss of privacy that comes with it?
18. What musical album could you play on repeat for hours at a time?
19. What is the healthiest and unhealthiest thing you do regularly?
20. How much should someone judge a person by their appearance?
21. If you found out that your current life has been only a dream, would you choose to wake up or stay in it?

21 Questions for a New Relationship

These questions are ideal for getting to know someone you’ve recently started dating. They provide insights into their beliefs about relationships and whether they’re seeking something more serious.

1. What are three non-negotiable traits you want in a partner?
2. What have you always dreamed someone would do for you?
3. What is your idea of the perfect relationship?
4. Do you believe opposites attract?
5. What is a common relationship belief that you don’t agree with?
6. Name one thing people do in relationships that drives you crazy.
7. Are you usually the first to apologize, or do you wait for the other person?
8. How do you handle conflict or opposing opinions with a significant other?
9. What quirky habit do you have that no one knows about?
10. What is your primary love language?
11. How would you want to spend a one-week vacation with your lover?
12. What or who inspires you to be a better person?
13. What did you learn about yourself from your last relationship?
14. What brings you the most joy in life?
15. What part of yourself have you learned to accept?
16. Who is a role model you want to be more like?
17. Imagine you’re dating the most attractive person in the world, but your family doesn’t like them. Would you stay with them? Why or why not?
18. Do you believe your significant other should start as your best friend?
19. How important is humor for you in a relationship?
20. Do you think that romantic partners should discuss their past relationships?
21. What is your favorite song to dance to?

21 Questions to Ask Your Crush

Navigating feelings for someone can leave you at a loss for words. These questions are subtly crafted to uncover more about them without being overly forward.

1. What is your favorite personality trait you look for in a significant other?
2. Who was your biggest celebrity crush as a teenager?
3. What is your definition of a healthy relationship?
4. Do you believe in soulmates?
5. What was your first impression of me?
6. When looking at someone you’re attracted to, where do your eyes go first?
7. What is the worst date you’ve ever been on?
8. Do you believe in astrology? Do you think our zodiac signs are compatible?
9. How old were you when you had your first kiss?
10. What did you dream of last night?
11. What is the biggest red flag in a relationship?
12. What is your biggest green flag?
13. What is the most spontaneous thing you’ve ever done?
14. Which is more important: Looks or smarts?
15. Do you think double texting is a big deal?
16. What is one thing you think everyone should master before they dive into a relationship?
17. If you went to a restaurant with terrible service, is it OK not to tip?
18. What is your biggest regret?
19. What is the most cringe thing you’ve ever said?
20. If you could live someone else’s life for a day, who would you choose?
21. What is something people misunderstand about you?

Flirty 21 Questions Ideas

Spice up your next date night with these tantalizing questions, perfect for both new connections and couples who’ve been dating for a while.

1. Do you believe in love at first sight?
2. What is your dream date?
3. What do you consider the most romantic travel destination in the world?
4. What is your biggest fear when it comes to relationships?
5. Romantic lunch picnic in the park or a high-class dinner and cocktails?
6. What’s your biggest turn-on?
7. Do you believe in fate?
8. Do you prefer cuddling or kissing?
9. Have you ever had a crush on a teacher or someone older than you?
10. What is your favorite love song?
11. What are the best and worst pickup lines you’ve ever heard of?
12. Love or money?
13. What is the shortest and longest relationship you’ve ever had?
14. What is the craziest thing you’ve ever seen someone do for love?
15. Would you consider yourself a hopeless romantic?
16. What is a relationship deal breaker?
17. What is your favorite thing about me?
18. What do you think is my favorite thing about you?
19. What sets you apart from other people?
20. What do you think sets me apart from other people?
21. What is the most attractive personality trait in a romantic partner?

21 Questions for Texting

If your text conversations are feeling a bit dull, these questions can inject some excitement and help you learn more about each other for the next time you hang out.

1. What’s your favorite movie of all time?
2. Do you have a hidden talent?
3. What is your biggest pet peeve?
4. What is your favorite childhood memory?
5. What is the last book you read?
6. Who is your favorite #couplegoals from a movie or social media? Send a screenshot or video link.
7. If you could describe yourself in 3 emojis, what would they be?
8. What GIF best describes you at work?
9. What GIF best describes you in a relationship?
10. What is your favorite inspirational life quote?
11. What do you listen to in the morning?
12. Whose voice is calming to you?
13. Whose voice irritates you?
14. What is your favorite way to spend your weekends?
15. If you had to choose your last meal, what would it be?
16. What makes you the happiest?
17. When was the last time your heart jumped?
18. When was the last time you laughed so hard that you cried?
19. What was your dream career as a child?
20. How would your friends describe you?
21. What song or playlist do you have on repeat right now?

Bonus Questions

Here’s a set of random questions for a “bonus round,” introducing unexpected topics into your conversation.

1. Why is getting out of your comfort zone so hard?
2. What is the worst lie you’ve heard an influential person tell?
3. What actor or actress would you want to play you in the movie of your life?
4. What is your guilty pleasure?
5. How would you be useful in a zombie apocalypse?
6. What is your favorite food to eat on vacation?
7. What is a bad habit that you want to beat?
8. Do you believe in aliens?
9. What was your favorite TV show as a kid?
10. If you could only wear one outfit for the rest of your life, what would it be?
11. What was the last concert you went to?

Key Takeaways: Use 21 Questions to Open Up New Conversation Topics

When it feels like you’re running out of conversation ideas, a game of 21 Questions can swiftly spark fresh topics. Whether you’re in the early stages of getting to know someone or aiming to delve deeper into an existing relationship, this classic game paves the way for more engaging conversations.

As a bonus, engaging in 21 Questions with a set of pre-prepared questions provides a “free pass” to discover more about someone without coming across as overly intrusive. Since it’s a game, people typically don’t take it as seriously as a single intense question. However, it’s essential to ensure you’re comfortable answering all the questions yourself before posing them to others.

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