21 Questions: A List Of 110+ Epic Questions! 

No matter if you want to get to know your crush better, or connect deeper with a friend of yours or a family member, ‘21 Questions’, the classic, lovely game, works like magic! And this is not even the best feature! Our favorite thing is that there are so many editions to choose from, depending on your relationship and goal. 

In a few minutes, you’ll get to know all the rules according to playing this no-cards game and our heart-to-heart tips. Also, most importantly, we’ll present to you all possible lists of questions, including funny ones, freaky, deep, and so on. With well-thought questions like these, you’ll never run away from conversations anymore! 

• How do you play 21 Questions?
• Funny & light questions;
• Deep questions;
• Freaky questions;
• Romantic questions;
• Family-friendly questions;
• Windup;

How Do You Play 21 Questions?

It’s impressive how simple this game is. In fact, we’re pretty sure you’ve played it at least once in your life. You can play it with as many people as you wish, however, it could also be a 2-player game! Now, if only 2 people are playing, you may take turns answering questions. 

There are several ways of playing if your group has 3 or more players. For instance, one of you may read one question, which should go around the group and everyone has to answer. Next, the other player going clockwise chooses another question, and the process repeats. 

You may also go the hard way and not let a player skip a question. This is usually played with people you’re super close with and everyone talks without filters. However, the most preferred way is playing the normal mode, meaning that once a player doesn’t feel comfortable, they can choose not to answer specific questions. 

In short words, you have to pick 21 questions from different categories or the same one and apply the above-mentioned rules. All categories include more than 21 questions, just in case you want to skip anything that doesn’t feel comfy.

If you also include drinking (such as drinking if you don’t answer), you will turn 21 Questions into Truth Or Drink, so, sure, go ahead! 

Funny & Light Questions 

There’s no better game to start the list rather than with funny questions, something to break the ice. Whatever category of questions you choose, make sure to pick a few of our below-mentioned since that’s what’s going to boost your laughter and make everyone feel welcome.

1. What’s the weirdest thing you’ve ever eaten?
2. Have you ever lied to get out of a date with someone?
3. If let’s say, you’ve farted in the elevator. Would you ask for an excuse, or blame it on someone else?
4. What would you do if you would woke up as the opposite sex for one day?
5. Is there any strange rumor you’ve heard about yourself?
6. What’s the cringiest thing you do in front of the mirror?
7. Do you have a favorite adult card game?
8. Where are you ticklish?
9. Have you ever picked your nose in public?
10. What’s something you would die if you’re family found out about?
11. What word do you hate most?
12. Do you have an embarrassing childhood memory?
13. Is there any gross smell you secretly enjoy? What is it?
14. Do you secretly dislike any of your friends’ kids?
15. What’s the worst gift you’ve ever given to someone?
16. What’s your cheesiest pick-up line?
17. Have you ever tasted your pet’s food?
18. What’s one inappropriate text you’ve sent to your family group?
19. Who’s someone non-famous you’ve stalked on social media recently?
20. What’s your most annoying nickname?
21. Did you believe in Santa back when you were a kid?
22. Do you ever read gossip blogs?
23. What’s the most useless late-night purchase you’ve ever made?

Deep Questions

For everyone willing to bond with people, we’ve made a list of deep questions! Lots of them are personal, so make sure everyone playing is comfortable with this category. Once you finish the questions, you’ll definitely know your mates better!

1. If you met a genie, what would your 3 wishes be?
2. When was the last time you apologized and why?
3. Which habit are your proudest of breaking?
4. What’s the most childish thing you still do?
5. Who in this room you would list in your emergency contacts?
6. What is one thing all your friends think is true, but is a complete lie?
7. If you knew you’d never get caught, who on Earth would you kill?
8. What’s your biggest fear in a relationship?
9. Do you have any ridiculous things that you’ve been attached to?
10. Who’s your hero?
11. When was the last time you bawled your eyes out crying in your room?
12. What’s your sweetest memory of childhood?
13. What are 3 words you would use to describe yourself?
14. Do you have any great regret in life?
15. If your life was a movie, what would it be called?
16. Would you rather go back in time or visit the future?
17. What year would you choose if you could travel through a time machine?
18. Of all the personal questions, people could ask, what’s one of them you wouldn’t want to ever answer?
19. What’s your favorite fictional character?
20. Do you believe in love at first sight?
21. What’s the riskiest thing you’ve ever done?
22. In what circumstance do you think cheating could ever be justified?

Freaky Questions

For everyone who’s been waiting for this category, don’t feel guilty! Just like in our Never Have I Ever list, you’ll now find a few questions, containing adult topics, absolutely not family-friendly, which we don’t doubt will be fully enjoyed!  

1. When’s the last time you’ve had a one-night stand?
2. Would you consider making out with your high school crush?
3. Do you enjoy reading erotic literature?
4. Have you been caught masturbating?
5. Who would you most prefer to kiss in this room?
6. Would you rather be a stripper or a porn star?
7. What’s your biggest turn-off?
8. How many sex toys do you own?
9. Who’s the weirdest person you’ve ever done the deed with? 
10. What’s the last sext you sent?
11. What’s the oldest age you’ve ever spent a night with?
12. Have you ever sent a sext to someone you shouldn’t?
13. What’s one disgusting practical joke you have tried on someone?
14. Have you ever had a wet dream?
15. Talk about your wildest dream.
16. Who has the nicest butt in this room?
17. What’s the last time you’ve peed your pants?
18. Who’s the person you regret kissing?
19. Name the hottest teacher you’ve met.
20. Have you ever been hit by someone of the same sex?
21. Do you enjoy dirty talk?
22. What’s your favorite position?
23. Who was your worst sexual partner?
24. Have you ever been to a nudist beach?

Romantic Questions

Here’s a special list for all our love birds, who are willing to play couples’ games. Questions will be very romantic and flirty, and we’re pretty sure it will help you and your significant other talk about things you couldn’t earlier. 

1. What was your first kiss like?
2. What’s your idea of a perfect date??
3. What do you like most about your partner, both physically and mentally?
4.  If there’s one thing you would change about our relationship, what would it be?
5. Have you ever tried online dating before getting into this current relationship?
6. How do you feel when your partner walks into a room?
7. Would you rather know everything about yourself or everything about your significant other?
8. What is the best thing to be in a relationship with your person?
9. Do you have any favorite body parts of your partner?
10. Rate your relationship on a scale from 1 to 10;
11. Have you ever snooped through your partner’s phone without them knowing?
12. What’s the worst date you’ve ever been on?
13. Tell your opinions in open relationships;
14. Do you wish your two were more intimate?
15. Where do you see your relationship in 5 years?
16. What did you think of each other when you first met?
17. Have you ever had a hot dream including your soulmate?
18. What is your favorite underwear of your partner?
19. What do you both think of PDA?
20. Who was your childhood crush?
21. Do you think there’s anything toxic about your relationship?
22. What’s the biggest pet peeve of your partner?

Family-Friendly Questions

21 Questions works great to connect deeper with your family members and talk things out. Such family games perform great and usually can be played by all ages, from kids to elders. You’ll probably cry out of cuteness… 

1. On a scale from 1 to 10, how messy is your closet?
2. Did you fake illness to skip school or any other event?
3. Would you trade your sibling for 1 million? (we know the answer);
4. If you could put one person on mute for one day, who would it be?
5. Did you believe that Santa exists?
6. Have you ever watched a TV show or movie you weren’t allowed to?
7. What is your favorite Disney movie?
8. Who’s one family relative you can’t stand?
9. What’s the funniest thing your grandparents have ever said?
10. Which animal would you like to be and what?
11. Who taught you how to tie your shoes?
12. Have you ever snitched about your siblings?
13. What’s your favorite dish mom makes?
14. Which supervillain would you like to be?
15. Do you have any weird talents?
16. What’s your favorite holiday?
17. Have you peed in the pool?
18. What’s your ideal way to spend family time?
19. Did you ever do something out of your interest just because your parents wanted you to?
20. What do you do when no one’s watching?
21. Who’s the funniest in your family?
22. Which is the worst gift you’ve ever received?

Windup

We’re absolutely in love with all the questions we just talked about. Make sure you pick your favorite category, the one that fits all players. Next, go through the questions, and start getting close with your people! 21 Questions has proved that it’s super successful and usually does great things for people’s relationships, especially for the ones struggling with communication and talking things out. Thank us later!