Getting to know someone is not 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 an interesting 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!
A Round of 21 Questions – The Rules of the 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, 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 by asking one question for the entire group. After that, every player will take turns answering the question until it gets back to person A. Then, person B asks one question that the entire group will answer, and it goes around the circle again. Another way to do this is to give everyone a piece of paper to write their answers to 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 precisely 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.
21 Questions Game List
Now, onto our 21 Questions game list! Everyone knows the game’s name, but ahead, we’re giving you more than 21 questions, from fun to embarrassing, romantic, and even some little flirty questions to get the fun going!
21 Questions for a Date to Remember
Scenario – you’re on a date with some cute guy/girl over coffee or brunch or over some cocktails in a fancy bar downtown. Whatever your dream date might 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 date jitters and awkwardness at bay. It will keep things light, fun, and enjoyable for both of you because dating is all about that. You are getting to know each other and trying to find out if there are things you have in common!
- Do you believe in love at first sight?
- 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.
- Are you usually open about your feelings or a little bit guarded?
- 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!
- Are you a lounge-in-the-pool or swim-in-the-beach kind of person? Or are they a morning person or night person?
- What is your current favorite movie or favorite TV show/TV series? Simple question but can lead to more conversations and follow-ups: why do they like it? Is it funny? Is it relatable? What is their favorite song?
- What are your weekends or days off from work reserved for? They might like to watch Saturday morning cartoons, and that might be a deal-breaker for you. Comparing favorite downtime activities is a compatibility check!
- Do you like your first kiss to be romantic or passionate?
- What are you currently looking for in a relationship, something casual or long-term? It’s always wise to get some realistic expectations early on. Flirting can be a game, but dating shouldn’t be!
- What is your biggest deal-breaker when it comes to relationships?
- What are your top five must-haves for your next relationship? 12. What’s the most incredible food you’ve ever tried? Because foodies unite, always! And don’t forget to table their answers for the 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!
- Can you describe your dream house?
- 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.
- What one word best describes your character?
- What’s your favorite thing about being part of a partnership/relationship?
- Where do you hope to be in the next five years? Not a job interview, but you’d want to know if there’s a space for you in their life plans before you’re too deep in the relationship.
- If you have the biggest pet peeve when it comes to dating, what is it?
- What was the biggest/most expensive gift you bought for yourself? Remember, you want to learn about this person and find out if you’re compatible, including learning their guilty pleasures.
- If you could give everyone you meet just one piece of advice, what would it be?
- If you could ask me only a single question right now and I had to answer it honestly, what would you want to know?
5 Naughty Question Substitutes
If both of you are ready for it (you’ll definitely know that after a couple of dates), there’s always some room to sneak in a few of these naughty substitute questions to find out if you’re compatible in other ways as well, like in the bedroom. Plus, it’s a great idea to level up the flirting and spice things up to make your date memorable!
- What was the worst sexual experience you’ve ever had? You’d want to know what things to avoid!
- Do you prefer showering alone or showering with someone?
- What makes sex really good for you?
- Is there anything you would never do in bed? It’s always smart to establish some boundaries.
- What is your greatest sexual fantasy? Getting to know them includes getting to know their desires, quirks, and their weirdest dream. After all, sexual compatibility would play a big role in your relationship.
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 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 freaking out inside. Okay, for starters, you don’t want to dig too deep. So, keep things light and build the appeal from there.
- What is your ideal date spot? Not an open invite (yet), but don’t forget to table that for later!
- How was your first kiss? Best guess? Probably awkward or a “terrible service.” But it could be a fun walk down memory lane, especially if the both of you share awkward first kisses!
- Romantically, are you looking for someone serious or just for right now?
- If you have a time machine and could give your ex one relationship tip, what would it be? If you want to replace the ex, you better listen to this one!
- What’s one thing that makes you instantly swipe left on a person?
- Have you been working out? Forget the silliest pick up line. This is the subtlest way to let them know you’re checking them out and most likely liking what you’re seeing!
- What is the silliest pick-up line you’ve ever heard?
- During a fight with your partner, do you walk away or yell?
- For a quiet night in watching a movie, are you more of The Notebook or Fifty Shades of Grey?
- What are you looking for romantically?
- What would you do if a friend of yours caught feelings for you? If you’re the “friend,” watch out for one of the most important pieces of intel you could ever find!
- At what point in your relationship/dating do you make it official on social media?
- What is the wildest/most scandalous thing you’ve ever done to keep a crush’s attention?
- What was the last flirty text/DM you sent someone?
- Have you spent the night with a blind date?
- What is your love language? It’s always good to know their love language if you’re thinking of going into a serious relationship.
- What is your biggest guilty pleasure in the bedroom?
- What is your biggest turn-on? Pro tip? Take note!
- What is your biggest turn-off? Even more important to take note of!
- What is one thing you can’t wait to do during your honeymoon?
- Do you just like me as a friend or something more? Make sure you all are ready to have this honest-to-heaven conversation!
5 Freakier Questions for Your Crush
The questions you’ve always dreamed of asking your crush but never really dared to voice out loud. Now is your chance! Sub out a few of the flirty questions above for these spicy, freaky questions: 22. How old were you when you watched an adult movie for the first time? 23. Would you put out on the first date if you really like the other person or play coy? 24. After a disagreement, do you initiate a makeup conversation or start a sexier makeup session before having a conversation? 25. Do you still think about your ex during sexy times? 26. Who is your friend you wanted to experience an intimate moment with but never really crossed the line? – it could be you (or not). It’s good to know either way!
21 Unexpected Funny Questions For 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. 27. What’s something you’ve dreamed of trying but never have? – you might be surprised. But it’s an opportunity to try something new together the next time you have an opportunity! 28. What is your biggest regret? 29. If you have a personal billboard, what would you put on it? – that is an incredible thing to think about. 30. What do you usually do when you are feeling down? – maybe they listen to a song, or go to the beach, or hang out with friends. 31. 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! 32. If you were to jump into a pool filled with something other than water, what would you pick? – now, that would give you an unexpected answer! 33. What is one thing you never tell people about you/what you do because you think it’s weird? 34. 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 really asking them what’s up. 35. What is the weirdest thing on your bucket list? 36. What do you consider is the weirdest thing you’ve ever done in your life? – it could be a spur-of-the-moment action, truth or dare game gone wrong, or a drunken mishap. Whatever it is, it would surely make a fun, if not interesting, conversation subject! 37. What is something that some of your friends don’t understand about you? – we’re all a little misunderstood, but this deep question for friends will help you be a better friend. 38. What is the most spontaneous thing you ever did during past relationships? 39. If you could have all the knowledge of one subject, what would it be? 40. What do you value more than anything else in the world? – it will give you a deeper, better understanding of their values and priorities. 41. If you could pay someone to do something for you, what would it be? 42. What’s the scariest risk you’ve ever taken that actually panned out? 43. What was the last word/thing you had to look up on the internet to see what it meant? 44. If you were a superhero, what would be your secret identity? 45. How long do you think you would survive in the zombie apocalypse? 46. What is something that you really want to accomplish in this lifetime? – an open-ended question that really helps you get to know a person. You might not know this thing about your best friend! 47. 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). When everyone’s bored and the energy of the party 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! 48. Have you ever been nude in public? – it could be a dare, or they just like to walk on the wild side! 49. What’s the craziest thing you have ever done inside a movie theater? 50. What is your favorite movie to watch when you want to get lucky on a date? 51. What’s the most embarrassing thing or photo you have on your phone? – and if they care to share the said photo in the group, that would be interesting. 52. If you had to give a kissing tip to someone, what would it be? 53. Would you consider marrying someone for their money? 54. What’s the most scandalous thing you’ve ever done with a partner? 55. During an overnight trip, would you rather share a bed with your best friend or her girlfriend/boyfriend? 56. If you had to trade your friendship over money, how much would you demand for it? – it’s friendship over by this point, but really, how much? 57. Who’s the most scandalous person you’ve ever slept with? 58. Would you ever consider marrying more than one person if you were allowed to do it? 59. What’s the worst lie you’d ever said to your significant other? 60. If you had to sleep with any person in this room, who would you choose? 61. Have you ever been caught checking someone out? – don’t forget to ask them to elaborate and share every detail of that awkward situation! 62. What’s your “I almost cheated” story? 63. Would you sleep with a guy/girl on the first date if you really like them? 64. What do you often do if you feel like you’re in the mood but don’t want to say anything to your partner? 65. What’s the biggest regret from your childhood? 66. Have you hooked up with someone you should never have? 67. If you had to play cupid for any two people in this room, who would you pick? 68. If we were inside your room right now, what would we be doing?
Final Thoughts on Playing the 21 Questions Game
There you are! Our awesome list of questions to get you started with a 21 Questions game for some interesting conversations and unexpected confessions! But 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 want to add.
