Want to have deeper conversations but don’t know where to start? Asking unique questions can make you more memorable and more likable! After all, who doesn’t want to share more about themselves?
If you’re bored with small talk, 21 Questions is a straightforward game that takes the edge off of first dates, new friendships, or work parties. It can also be used to dive deeper into your relationships with anyone in your life. Here is everything you need to know about how to play the 21 Questions game, plus the best questions to ask for more compelling conversations.
What is “21 Questions”?
21 Questions is a conversation-starting game that involves asking a series of questions to learn more about somebody. It can be played online or in real life and works with two people or a larger group. This simple game demonstrates your interest in learning about others while also allowing you to spill some secrets about yourself.
Ideally, 21 Questions sparks new discussion topics between you and the other player(s). But if you’re still struggling with awkward silences and small talk, you may want to practice some conversation hacks to keep the dialogue flowing. Like riding a bike, anyone can learn to be a master conversationalist.
Check out our workshop, where communication expert Vanessa Van Edwards teaches you to talk to people with more confidence and emotional intelligence:
And if you want to really level up your social skills, check out our goodie!
Communicate With Confidence
Do you struggle with small talk? Do you often run out of things to say or feel awkward and self-conscious in social situations? Our Conversation Mastery Course teaches you the secrets of master conversationalists and gives you the skills you need to have confident, engaging, and captivating conversations with anyone, anywhere.
How to Play 21 Questions
The 21 Questions Game is extremely simple. The only real rule is honesty. You can play with two or more people in a variety of settings. All you need is a list of situation-appropriate questions and a place to hang out while you answer them. You can even play over text!
There are a few different ways to play 21 Questions:
- Round and Round Questions: The classic 21 Questions game is played with a group of people. The first person chooses a question, and then the group goes around a circle so each person can answer. Optionally, you can allow everyone 1 “skip” for a question they don’t want to answer.
- Ricochet Questions: If you only have two people, this version of 21 Questions involves going back and forth, so you each have an opportunity to answer the question at hand. Person A asks a question, and Person B has to answer. Then Person B chooses a different question, and Person A has to answer. This is great for a romantic date or friendly meetup because there is plenty of time to discuss your answers before you move to the next question.
- Rapid Fire: For couples or friends who want to get deeper into each other’s “raw” answers, a rapid-fire game involves asking one person 21 questions in a row. After all 21 questions are complete, the roles are reversed, and the first person answers the same questions.
The key to a successful 21 Questions game is to choose the right questions for the occasion. It’s best to avoid overly invasive or intimate topics in a group setting, but you may want to use juicier questions to spice things up with a significant other whom you’ve known for a while.
Below, we share 21 Questions ideas for:
- Getting to know someone
- A new relationship
- A new crush
- Flirty questions
- Texting a friend
110 Best Questions for 21 Questions Game
Instead of asking bland questions like “What’s your favorite color?” or “What do you do for a living?” these ideas for 21 Questions are thought-provoking and intriguing. But before you play, read through the lists and ensure you feel comfortable asking and answering every question. If not, you can always eliminate questions or make up your own!
21 Questions to Get to Know Someone
These questions go beyond work and hobbies to understand more of how someone sees the world. This list is inquisitive and sometimes philosophical without getting too personal.
- If you could travel to any point back in time, what year would you choose and why?
- What are a few things at the top of your bucket list?
- What decision do you look back on and say, “What was I thinking?”
- If you could give your 16-year-old self one piece of advice, what would it be? Would you have listened?
- Who is/was the most influential person in your life?
- What is the first thing you would do if you won the lottery?
- What is the weirdest dream you’ve ever had?
- If you could have any superpower, what would you choose and why?
- What is the most embarrassing thing you’ve done in public?
- Would you consider yourself adventurous, or do you play it on the safe side?
- What is your go-to karaoke song?
- What would you title this chapter of your life?
- If you could re-live any part of your life so far, which part would you choose and why?
- What is the biggest lesson you learned from your teens/twenties?
- Who would you want to sit next to on a ten-hour flight across the world, and why?
- If you could be any kind of dog, what breed would you be?
- Do you think the convenience of the internet is worth the loss of privacy that comes with it?
- What musical album could you play on repeat for hours at a time?
- What is the healthiest and unhealthiest thing you do regularly?
- How much should someone judge a person by their appearance?
- 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 are the perfect questions to ask someone you just started dating. You can find out more about their beliefs on relationships and whether or not they’re looking for something serious.
- What are three non-negotiable traits you want in a partner?
- What have you always dreamed someone would do for you?
- What is your idea of the perfect relationship?
- Do you believe opposites attract?
- What is a common relationship belief that you don’t agree with?
- Name one thing people do in relationships that drive you crazy.
- Are you usually the first to apologize, or do you wait for the other person?
- How do you handle conflict or opposing opinions with a significant other?
- What quirky habit do you have that no one knows about?
- What is your primary love language?
- How would you want to spend a one-week vacation with your lover?
- What or who inspires you to be a better person?
- What did you learn about yourself from your last relationship?
- What brings you the most joy in life?
- What part of yourself have you learned to accept?
- Who is a role model you want to be more like?
- 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?
- Do you believe your significant other should start as your best friend?
- How important is humor for you in a relationship?
- Do you think that romantic partners should discuss their past relationships?
- What is your favorite song to dance to?
21 Questions to Ask Your Crush
It’s easy to get tongue-tied when you catch feelings for someone:
These questions are subtle enough to learn about them without being too forward.
- What is your favorite personality trait you look for in a significant other?
- Who was your biggest celebrity crush as a teenager?
- What is your definition of a healthy relationship?
- Do you believe in soulmates?
- What was your first impression of me?
- When looking at someone you’re attracted to, where do your eyes go first?
- What is the worst date you’ve ever been on?
- Do you believe in astrology? Do you think our zodiac signs are compatible?
- How old were you when you had your first kiss?
- What did you dream of last night?
- What is the biggest red flag in a relationship?
- What is your biggest green flag?
- What is the most spontaneous thing you’ve ever done?
- Which is more important: Looks or smarts?
- Do you think double texting is a big deal?
- What is one thing you think everyone should master before they dive into a relationship?
- If you went to a restaurant with terrible service, is it OK not to tip?
- What is your biggest regret?
- What is the most cringe thing you’ve ever said?
- If you could live someone else’s life for a day, who would you choose?
- What is something people misunderstand about you?
Flirty 21 Questions Ideas
Use these juicy questions to spice up your next date night. These can be used for new connections or for couples that have been dating for a while.
- Do you believe in love at first sight?
- What is your dream date?
- What do you consider the most romantic travel destination in the world?
- What is your biggest fear when it comes to relationships?
- Romantic lunch picnic in the park or a high-class dinner and cocktails?
- What’s your biggest turn-on?
- Do you believe in fate?
- Do you prefer cuddling or kissing?
- Have you ever had a crush on a teacher or someone older than you?
- What is your favorite love song?
- What are the best and worst pickup lines you’ve ever heard of?
- Love or money?
- What is the shortest and longest relationship you’ve ever had?
- What is the craziest thing you’ve ever seen someone do for love?
- Would you consider yourself a hopeless romantic?
- What is a relationship deal breaker?
- What is your favorite thing about me?
- What do you think is my favorite thing about you?
- What sets you apart from other people?
- What do you think sets me apart from other people?
- What is the most attractive personality trait in a romantic partner?
21 Questions for Texting
If your text convos have gotten a little stale, these questions can help you learn more about each other for the next time you hang out.
- What’s your favorite movie of all time?
- Do you have a hidden talent?
- What is your biggest pet peeve?
- What is your favorite childhood memory?
- What is the last book you read?
- Who is your favorite #couplegoals from a movie or social media? Send a screenshot or video link.
- If you could describe yourself in 3 emojis, what would they be?
- What GIF best describes you at work?
- What GIF best describes you in a relationship?
- What is your favorite inspirational life quote?
- What do you listen to in the morning?
- Whose voice is calming to you?
- Who’s voice irritates you?
- What is your favorite way to spend your weekends?
- If you had to choose your last meal, what would it be?
- What makes you the happiest?
- When was the last time your heart jumped?
- When was the last time you laughed so hard that you cried?
- What was your dream career as a child?
- How would your friends describe you?
- What song or playlist do you have on repeat right now?
- If you are in a bad mood, what could cheer you up every time?
- Would you move across the world for someone you love?
- What is the nicest thing anyone has ever done for you?
- If you could describe yourself in one word, what word would you choose?
- Do you believe in karma? Why or why not?
Here are some random questions to add for a “bonus round” of unexpected topics.
- Why is getting out of your comfort zone so hard?
- What is the worst lie you’ve heard an influential person tell?
- What actor or actress would you want to play you in the movie of your life?
- What is your guilty pleasure?
- How would you be useful in a zombie apocalypse?
- What is your favorite food to eat on vacation?
- What is a bad habit that you want to beat?
- Do you believe in aliens?
- What was your favorite TV show as a kid?
- If you could only wear one outfit for the rest of your life, what would it be?
- 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 quickly inspire new topics. Whether you’re just getting to know someone or trying to dig deeper into an existing relationship, this classic game opens the door for more compelling conversations.
As a bonus, playing 21 Questions with a list of pre-prepared questions gives you a “free pass” to learn things about someone without feeling too nosey. Because it’s a game, people don’t usually take it as seriously as a single intense question. Make sure you feel comfortable answering all the questions yourself before you ask them!
Want more question ideas for better conversations? Here are 450 Fun Questions to Ask People in ANY Situation (That Work!)