21 Questions The Ultimate Get To Know You Challenge

Getting to know someone is not something that’s easy to do for all of us. Whether that’s a new friend, a new colleague, or someone you’re on a date with. Even outright asking your best friends some deep or juicy questions can seem awkward. So, where do you even start?  Playing the 21 questions game might just be the ice breaker you need! And for that, we’ve rounded up some of the greatest questions designed to spark great conversations with anyone and everyone you have in mind.  Whether you are making new friends at school or in the office, getting to know someone new over coffee or a glass of wine at dinner, or killing time during a road trip with friends, these questions can help build friendships, both new and old, and even spark flames. And it’s a straightforward game with one cardinal rule – answering questions honestly! 

How to Play the 21 Questions Game

The 21 Questions game is a classic and has been around for ages. But if you need a refresher on the game’s rules, here’s a roundup of how this game should be played. It’s easy! First of all, you’ll need at least two players, but more is always better. The simple rule is that each player has to answer 21 questions. However you want to play it, you decide! But here are some options:

Classic 21 Questions

If it’s just two people playing, you can bounce off questions to each other. Now, when playing in a group setting, the simplest way to play 21 Questions is to take turns asking each other questions. For example, Player A asks player B a question, then after player B answers and it’s their turn to ask player C a question, and so on until the question goes back to player A.  It will be fun if you stand or sit in a circle and use a ball, handing it out to the next person when it’s their time to ask 21 questions. 

The Hot Seat

This version of the game is where you put one player in the hot seat. Someone can volunteer, or you choose the first person randomly, and the rest of the group takes turns asking the person in the hot seat a total of 21 questions. After that, they can either ask new questions or ask follow-up questions.  For the next round, the person answering 21 questions nominates the next one to take the hot seat.

The Pop Quiz

This 21 Questions game variation is the opposite of the “hot seat.” Instead of one person answering 21 questions, person A starts with asking one question for the entire group. Every player will take turns answering the question until it gets back to person A, then person B asks one question that the whole group will answer, and it goes around the circle again.  Related Reading: Questions to Ask Friends Another way to do this is to give everyone a piece of paper to write their answers on all 21 questions and then take turns viewing each other’s answers in front of the group. 

Get-Out-Of-Jail Free Cards

It won’t be a fun question game if you’re not going to ask them for some juicy details and confessions. But before the game begins, you have to account for those potential skips unless everyone is willing to play the “hard mode,” where you can make it mandatory to answer every question. Otherwise, set the rules on how many skips a player has in case they don’t feel too comfortable answering the burning questions.  And one last thing, do you have to ask exactly 21 questions?  Of course, not! It’s your game, so you decide how many questions you want to ask. But if you’re playing ‘The Hot Seat,’ setting a number of questions to ask might be best.

The Ultimate List of 21 Questions for Every Occasion

Now, onto our 21 Questions game list! We’re giving your more than 21 questions, from embarrassing and funny questions to romantic ones and even a few naughty ones to keep the fun going! Related Reading: How to Make Friends as an Adult

Keep It Simple With 21 Gentle Questions

There are a lot of possible questions you can ask your friends in this game, but before you need to walk before you run. So let’s look at some classic warm-up questions for the early rounds. The following questions are great to warm up the crowd and get everybody comfortable with the idea of answering questions in a group. Some people struggle with that concept, and so a gentle way into the 21 questions game is the ideal way to start.

1. What is your favorite movie?
2. What would your dream house look like, and where would it be?
3. What’s the most spontaneous thing you have ever done?
4. What is your biggest guilty pleasure?
5. Do you already have a bucket list?
6. What do you enjoy more, online games or board games?
7. What was the last concert you went to?
8. What is your biggest regret?You can tweak this one to cover the biggest overall regret or the biggest regret in a relationship.
9. What is the worst lie someone has ever told you?Maybe change this one up, so by worst, you mean, most unconvincing!
10. What is the weirdest dream you’ve ever had?
11. What was your dream job when you were a child?
12. If we were in the zombie apocalypse, what one thing would you have to have with you?
13. Who is the most famous person you have ever met?
14. Are you a morning person or a night person?
15. What do you think your best personality traits are?
16. What is your favorite song?This can be appended with all manner of options; a favorite song in general, for getting ready to go out, or for in the gym, etc.
17. If a time machine existed, what period of time would you go back to first?
18. What fun games do you like playing?
19. What’s the most embarrassing thing to have ever happened to you?
20. What is your favorite sport?
21. What is your favorite season?

21 Questions Game on a Date? Why Not!

Scenario – you’re on a date with some cute guy/girl over coffee or brunch; perhaps you’re enjoying a few cocktails in a fancy bar downtown or whatever your dream date night be. Sounds romantic? Yeah, right, until you start that boring conversation about the weather, politics, or what you did last summer. Or worse, the silence gets a little too awkward, and now you’re wondering why you’re there in the first place. Because we’re not all great conversation starters! So, here’s a better deal – play a questions game to keep those awkward first-date jitters and awkwardness at bay. It will keep things light, fun, and enjoyable for both of you because that’s what dating is all about. You are getting to know each other and trying to find out if there are things you have in common! 

1. What is your favorite time of day?It’s a gentle question but also important to figure out if you are dating a morning or a night person.
2. How do you prefer to spend/use your free time?You’ll want to know what they like to do for fun if you’re going to hang out with them often. 
3. Are you usually open about your feelings or a little bit guarded?
4. What adventures or hobbies would you like to do or experience but haven’t had the time to do them yet?If all goes well, this could be your next date idea!
5. Are you a lounge-in-the-pool or swim-in-the-beach kind of person?
6. What is your current favorite movie or favorite TV show/TV series?It is a simple question but can lead to more conversations and follow-ups: why do they like it?
7. If you were a superhero, what would your secret identity be?This is an interesting question as it gets people to open up more about their true selves.  
8. Do you believe in love at first sight?This is a dangerous one for a first date and should only be used if things are going well, and it’s clear that the question is not a declaration.
9. What would be your idea of a dream date?
10. What are your weekends or days off from work reserved for?They might like to watch Saturday morning cartoons, which might be a deal-breaker for you. However, comparing favorite downtime activities is a compatibility check!
11. If you went to a restaurant with terrible service, how would you handle it?
12. What’s the most incredible food you’ve ever tried?Because foodies unite, always! And don’t forget to table their answers for next time you choose a restaurant for your date. Or it could be something made by their family, and you can ask if they want to share their memories about it or who made it!
13. If you could be one fictional character, who would it be and why?
14. What is your ideal work-life balance?It’s fine to date a workaholic, especially if it’s their dream job, but it’s always nice to know where their priorities lie beforehand. 
15. What are your most treasured childhood memories?
16. What’s your favorite thing about being part of a partnership/relationship?
17. Where do you hope to be in the next five years?  
18. What is your biggest pet peeve?
19. What was the biggest/most expensive gift you bought yourself?Remember, you want to learn about this person and find out if you’re compatible, including learning their guilty pleasures. 
20. If you could give everyone you meet just one piece of advice, what would it be?
21. What’s the craziest thing you’ve ever done to get your crush’s attention?

21 Questions Game with a Crush? Here’s a List of Flirty Questions!

Crushes are fun until you try starting a conversation with them. It’s kind of the best and worst feeling at the same time! You get super nervous and lose your words. Don’t worry! We’ve rounded up a list of getting-to-know-you questions to ask your crush. Sneak these questions on someone you really like to know a little better. But most of all, a 21 Questions game is a fantastic way to gather some intel (subtly!) and see if they are as into you as you are into them!  Jot these questions down, so the next time you’re face to face with your crush, you’d know how to keep the convo going even when you are totally freaking out inside.  Okay, for starters, you don’t want to dig too deep. So, keep things light and build the appeal from there. 

1. What is your ideal date spot?
2. How was your first kiss? – best guess?It’s probably awkward or a “terrible service,” But it could be a fun walk down memory lane, especially if both of you share your embarrassing first kiss stories!
3. How long was your last relationship?
4. If you have a time machine and could give your ex one relationship tip, what would it be?
5. What’s one thing that makes you instantly swipe left on a person?
6. What do you think is the most important factor behind a good first impression?
7. Who was your first celebrity crush?
8. What is the weirdest thing on your bucket list?
9. What is the silliest pick up line you’ve ever used?
10. What are you looking for romantically?
11. What would you do if a friend of yours caught feelings for you?This could give you all sorts of information should you decide to make a move.
12. What is your favorite food?
13. What is the wildest/most scandalous thing you’ve ever done to keep a crush’s attention?
14. What was the last flirty text/DM you sent someone?
15. Have you ever been on a blind date?
16. Is physical appearance a big deal if you match with someone’s personality?
17. What is your guilty pleasure movie?
18. What is your biggest turn-on?
19. What is your biggest turn-off?
20. What is your favorite game to play on a rainy afternoon?
21. What is the one bad habit you wish you could kick?We all have room for self improvement, so it’s interesting to find these things out early in case its a deal-breaker.

Fun and Unexpected 21 Questions Game with Your Friends

Do you think you know everything to know about your friends? Why not test how well you know your BFFs with a 21 Questions game? We’ve curated a mix of light, fun, and deep questions to ask your best buds, designed to get the most interesting and unexpected answers. It’s perfect for game nights or long road trips when you’re done belting out to your favorite on-the-road playlist. 

1. What’s something you’ve dreamed of trying but never have?
2. What is your great idea of a good time?
3. If you have a personal billboard, what would you put on it?This is a surprisingly deep question to think about. 
4. What do you usually do when you are feeling down?
5. What is one thing that many people think is “cool,” but you think is the dumbest thing ever?Get ready for a fun (or heated) debate!
6. If you were to jump into a pool filled with something other than water, what would you pick?
7. What is one thing you never tell people about you/what you do because you think it’s weird?
8. What do you spend so much time thinking about these days?If you haven’t been together for a while, it’s a great way to ask them how they are without asking them what’s up. 
9. How would you describe yourself, for Santa‘s sake, naughty or nice?
10. What do you consider is the weirdest thing you’ve ever done in your life?It could be a spur-of-the-moment action, a truth or dare game gone wrong, or a drunken mishap. Whatever it is, it would surely make a fun, if not interesting, conversation subject!
11. What is something that some of your friends don’t understand about you?
12. Do you have irrational fears?
13. Do personal questions make you feel uncomfortable?
14. What do you value more than anything else in the world?It will give you a deeper, better understanding of their values and priorities. 
15. If you could pay someone to do something for you, what would it be?
16. What’s the scariest risk you’ve ever taken that actually panned out?
17. Are you a faithful person when in a long term relationship?
18. Are you a fan of celebrity news and gossip magazines?
19. What is the biggest lesson you have learned from past relationships?
20. What is something that you want to accomplish in this lifetime?An open-ended question that helps you get to know a person. You might not know this thing about your best friend!
21. If you could make up a new holiday, what would you name it?

21 Questions Game for Friends – the Juicy Questions Version!

Here’s the thing about friendships – you can pry and get away with it (most of the time). And when everyone’s bored and the party’s energy is winding down, you can ask the juiciest questions to your friends, and it would be fair game.  So, here’s your chance to ask your friends some spicy questions, and it might reveal some of the things you never knew about them yet. But revelations aside, this list of juicy 21 questions are a guaranteed starter of interesting conversations!

1. Have you ever been nude in public?It could be a dare, or they just like to walk on the wild side!
2. What’s the craziest thing you have ever done inside a movie theater?
3. What was the last sexy dream you had?
4. What’s the most embarrassing thing or photo you have on your phone?If they care to share the said photo in the group, that would be interesting. 
5. If you had to give a kissing tip to someone, what would it be? 
6. Would you consider marrying someone for their money?That would be interesting to hear from any friend. 
7. What’s the most scandalous thing you’ve ever done with a partner?
8. During an overnight trip, would you rather share a bed with your best friend or their girlfriend/boyfriend?
9. If you had to trade your friendship over money, how much would you demand for it?
10. Who’s the most scandalous person you’ve ever slept with?
11. What one word best describes your skills in the bedroom?
12. What’s the worst lie you’d ever said to your significant other?
13. If you had to sleep with any person in this room, who would you choose?
14. Would you ever sleep with someone you crushed on if you knew they were in a serious relationship?
15. What’s your “I almost cheated” story?
16. How did your last real relationship end?
17. What do you often do if you feel like you’re in the mood but don’t want to say anything to your partner?
18. What’s the biggest secret you’ve been keeping from everyone in the room?
19. What’s the weirdest dream you’ve ever had about getting busy in the bedroom?
20. If you had to play cupid for any two people in this room, who would you pick?
21. Have you ever been caught double texting two crushes?

Final Thoughts – Do You Dare Play the 21 Questions Game?

There you are! Our awesome list of questions to get you started with a 21 Questions game. Whether you are looking for some interesting conversations or hoping to hear some unexpected confessions, these questions have you covered. However, feel free to add some of your own questions too.  Share in the comments how you would play this game and other fun, creative, revealing, and even strange questions you would add.