21 Questions Game: 60+ Fun, Deep & Flirty Questions

What Exactly Is the 21 Questions Game?

How to Play the 21 Questions Game: The three easy rules

• Take turns: One person asks another person a question from a list of 21 questions. After the question is answered, the roles are then the opposite. The person who just answered is now allowed to ask a question.

• Be honest: the game works best when the answers are real. It's a chance to be open and honest, so try to give thoughtful, honest responses.

• The "Pass" Option: If a question is too personal or you don't want to answer it, you can usually have one or two "passes" during the game. But try not to use too many of them, as the best things are often shared!

60+ Questions to help you remember any situation

Icebreaker Questions (For New Friends)

• What skills do you wish you had?

• If you could have any superpower, what would it be and why?

• What's the best concert you've ever been to?

• What was your favorite cartoon as a child?

• If you could travel through time, would you go to the past or the future?

• What's the most adventurous thing you've ever eaten?

• Are you an early bird or a night owl?

• What's a film you can watch over and over again?

• If you could live anywhere in the world for a year, where would you go?

• What's one thing you really want to do before you die?

• Do you have any hidden talents?

• What is the strangest job you have ever had?

• What popular TV show haven't you seen?

• If you had to describe yourself as an animal, which one would it be?

• What's your favorite karaoke song?

Deep & Meaningful Questions (For Closer Connections)

• What are you most grateful for in your life right now?

• What was one mistake you made that taught you a valuable lesson?

• What does "success" mean to you?

• If you could give your younger self one piece of advice, what would it be?

• What do you fear the most?

• Who has had the most influence on your life?

• What's a dream you've had for a long time but haven't done yet?

• What is the most important thing for you in a friendship?

• What do you do to relax after a stressful day?

• What are you proud of, but don't get to talk about often?

• What does a perfect day look like for you?

• What is one belief you have that many people disagree with?

• When do you feel most like your true self?

• Can you think of a book or a film that has changed the way you think about something?

• What do you want to achieve in the next five years?

Fun & Quirky Questions (To Spark Laughter)

• If you were a ghost, where would you haunt?

• What's the most ridiculous thing you've ever bought?

• You have to live in a video game forever. Which one do you choose?

• What's the funniest way you've ever injured yourself?

• If animals could talk, which species would be the rudest?

• What's a weird food combination you absolutely love?

• If you were arrested and no one knew why, what would your friends and family think?

• What conspiracy theory do you think might be true?

• You can have as much as you like of anything, but money is not something you can have too much of. What is it?

• What's the silliest thing you've ever argued about?

• If you could add a 27th letter to the alphabet, what sound would it make?

• What would you call your autobiography?

• What's a saying or phrase that you really don't like?

• If you had to replace your hands with objects you already have at home, which ones would you choose?

• What's the most pointless fact you know?

Flirty & Romantic Questions (For Your Crush or Partner)

• What did you think of me when you first met me?

• What turns you on the most?

• When did you first realize you fancied me?

• What does a perfect romantic holiday look like?

• What song makes you think of me?

• What do you like most about my personality?

• What's your favorite memory of us so far?

• How do you like to show and receive love?

• What is something you've always wanted to try in a relationship?

• What is one thing you think I don't know about you?

• What makes a kiss perfect?

• If we could go on a date anywhere in the world, where would we go?

• What's something small I do that makes you happy?

• What are you most excited about for our future together?

• In one word, how would you describe the feeling I give you?

Pro Tips for the Best Game Ever

• Listen carefully: Don't just think about the next question you're going to ask. Pay attention to the answers. This is where people can really connect. There are studies that show how important it is to be a good listener if you want to get on with people. These studies were done at places like the University of Minnesota.

• Ask follow-up questions: If you're curious about an answer, ask "Why?" or "Can you tell me more about that?" This shows you're serious about your relationship.

• Share your answers: Make it a two-way street. After they have answered, you can share your own thoughts on the question to help build trust.

• Stay Curious: Approach the game with a real interest. [Check out our other conversation starters for more ideas! - internal link].

Make your answers last forever with Tellsomething

• Ask a question: Pick one of the powerful questions from the list above.

• Capture the Moment: As they share their answer, think about a photo or a short video that shows what their story is all about. Maybe it's a picture of the place they're talking about or a short video of them smiling as they remember a happy moment.

• Create your post: Go to Tellsomething. Add their answer to your post and upload a photo or video to make it more interesting.

• Write your story:Over time, you can create a collection of these moments, building a rich multimedia journal of your relationship, friendship, or even your own self-discovery.