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Getting to know someone can be tough. Your hands get sweaty, you start to stutter and nothing but brainfarts come out of your mouth. Sounds familiar? The 21 Questions game could be your solution!

This question and answer game can be an opportunity to deepen a relationship of your choice!

How to play 21 Questions

The basic rules are pretty simple: One player asks a question and another player answers.

If you’re just 2 players, you can either play one-sided or two-sided. But if you’re more than 2 players and want to make the game more interesting, take a look at the game variations below.

And always remember, the goal of the game isn’t answering the questions. The goal is to achieve an interesting conversation!

The target version

In this version of the game 21 Questions, you start by randomly choosing one person as the target. You could play rock paper scissors, spin a bottle, or find your own way to decide randomly.

Now the other players ask 21 questions and the chosen player answers them.

After the first round, the player who finished answering nominates the next person to be the target.

The circle version

As you might have guessed from the name, all players get together in a circle. Then you decide who gets to start. You can either decide randomly or maybe someone volunteers.

Now the first player asks one question. The player to his right starts to answer the question, then the next player in line and the next until everybody including the first player has answered it.

After the first round, the next player in line asks the second question. And again, everybody answers it.

The dice version

The dice version is pretty similar to the target version of the 21 Questions game.

At first, you choose a target player randomly. Then this player rolls two dice. How many questions the player needs to answer depends upon the dice rolled and its numbered faces.

For example: Player 1 rolls “4” and “3”. Now the other players ask him seven questions.

Tip: If you just have one die, remember the rolled number, throw it again and add the two numbers.

The 7 questions version

In the 7 questions version of the game, you just divide the questions between the players.

For example: If you are three players, everyone answers seven questions.

Tip: If the number of people is unable to divide evenly into 21, maybe just expand your list until the dividing is possible.

Game rules: 21 Questions

  1. Don’t be judgy! Nobody should judge any answer. If you don’t have anything nice to respond to, maybe just be quiet.
  2. Show respect! Yes, personal or even embarrassing questions can be fun. But pay attention and don’t make anyone feel uncomfortable while playing. Just treat them the same way you’d like to be treated.
  3. Be honest! Nobody likes liars.
  4. Don’t copy questions! It’s boring to hear the same questions over and over again. Be creative and come up with your own questions or take a good look at our list.
  5. Keep the conversation going! Try and add a “why” after some questions to start a deep conversation. Some stories behind an answer are even more interesting than the answer itself.

List of 21 questions to ask

We have collected 100+ questions for your 21 Questions game! Here you are guaranteed to find questions for every occasion.

21 Questions for a new relationship

The following questions are perfect to deepen a your new relationship. By using these questions, we guarentee a fun game night with the opportunity of getting to know the person of you choice!

1. If your life was a movie, what would it be called?

My life would be Harry Potter. Just because I want to be in Hogwarts!

2. What is the last concert you went to?

Don’t we all like to talk about music?

3. What do you wish you were really good at?

Everyone has at least one thing that they would like to be really good at.

4. If you were a dog, what kind of dog would you be?

I would be a golden retriever.

5. Do you shower at night or in the morning?

Or maybe in the morning and in the evening?

6. If you go to a restaurant and have terrible service, is it ever okay not to tip?

Puh, that’s a tricky one.

7. If you could be any animal, what would you be?

Would you rather be a mammal, a bird, or even an amphibian? You might want to be a wasp and sting people you don’t like. I would understand.

8. If you had to rename yourself, what name would you choose?

Surely you would choose an extraordinary name.

9. What was the last show you binge-watched?

Friends, Game of Thrones, How I Met Your Mother, or Big Bang Theory? There are so many great series out there. Pick one!

10. Who is your secret hero?

Hm, maybe your mother?

11. If you had a time machine, would you go back in time or visit the future?

Both would be SO interesting. It’s hard to choose.

12. If you could only hear one song for the rest of your life, what would it be?

Choose wisely.

13. What is the worst lie you’ve ever told your parents?

Yes, you shouldn’t lie… But sometimes it just happens!

14. If any actor or actress could play you in a movie, who would it be?

Would it be Keira Knightley, Jennifer Aniston, or Jennifer Lawrence? Or Tom Hanks, Morgan Freeman, or Tom Cruise?

15. What is the weirdest dream you’ve ever had?

Dreams can really be scary sometimes.

16. Are you more of a morning or night person?

I am definitely a night person.

17. What is your go-to karaoke song?

I wanna feel the heat with somebody! Yeah, I wanna dance with somebody, with somebody who loves me…

18. If you could move anywhere in the world, where would you go?

There are so many beautiful places in the world. What is your favorite country?

19. What is the biggest lesson you’ve learned?

Hm, that’s a tricky question.

20. What was your favorite game as a child?

It doesn’t matter whether it’s a virtual or an analog game. Just the first game that comes to your mind!

21. If you could visit one place on earth where would you go?

Yes, where would you go?

21 Questions to ask your crush

You’re secretly in love with the girl next door? Or with a boy in your class? Don’t worry. The next list will be perfect for you because we listed questions to ask your crush.

We’ve collected this list of 21 questions to ask your crush for you as possible conversation starters to create intimacy. Some of them are nice for the first talk, some of them fit perfectly in first date situations but some of them also work after a couple of months in a relationship.

1. Do you think double texting is a big deal?

Ahm, yes?!!

2. When did you have your first kiss?

The first kiss… I bet there’s a cute story behind this answer!

3. Do you believe in astrology? Does your sign fit you?

It says a lot about a person if they believe in zodiac signs.

4. What is the most spontaneous thing you’ve ever done?

Let’s be spontaneous now!

5. What is your biggest regret?

You shouldn’t regret anything. You can’t change the past anyway.

6. What is your dream date night?

Maybe your crush has dreamed of you!

7. How would you describe your relationship with your family?

Are you close to your family or not?

8. Are you looking for a relationship? Why do you say so?

This is a really important question to ask your crush.

9. Do you ever think about me?

And? Do you?

10. What attracts you to people?

Hopefully, your crush isn’t just paying attention to looks. That would be SO boring.

11. Are you a virgin?

That is a very intimate question.

12. Do you think you’re a good kisser?

Don’t we all think we’re good kissers?

13. What was the best part of your day?

Let’s talk about your days!

14. What was the last book you really got into?

I hope you know the most important rule of all: Don’t sleep with people who don’t own books!

15. Do you fall for a person fast?

This is also really important to ask your crush.

16. What was one time you really stepped out of your comfort zone?

Stepping out of your comfort zone can be really scary!

17. How did your last relationship end?

Hopefully, your crush hasn’t cheated on anyone.

18. What is your biggest guilty pleasure?

Do you still love watching Hannah Montana? Do you like listening to Britney Spears? Tell your secrets!

19. If you were a superhero, what kind of secret identity would you have?

I would be like Spiderman. (Or better Spider-woman?)

20. How would be your ideal partner?

Hopefully, your crush will respond in great detail!

21. How old were you when you started dating?

That’s really important as well.

21 Questions to ask your partner

Yes, the game 21 Questions also works for couples. The following questions are made for getting to know your significant other on a deeper level.

1. Who was your first crush?

And best of all, tell each other how the story ended.

2. What was the happiest moment of your life?

Maybe the moment you met?

3. What is your favorite smell?

Mhm… There is hardly anything better than good smells!

4. What is the most embarrassing thing you’ve ever done to get a crush’s attention?

Please, tell each other the whole story!

5. What is the strangest way you’ve become friends with someone?

Your partner probably already knows the story.

6. Have you ever cheated on someone?

I hope not.

7. What is the most ridiculous thing you’ve done because you were bored?

Let’s be honest with each other!

8. When you were a kid, what seemed like the best thing about being a grown-up?

Children always imagine adulthood to be far too idyllic.

9. Have you ever been cheated on?

If so, I’m very sorry for both of you.

10. What took you way too long to figure out?

A friend of mine didn’t learn how to read the clock correctly until she was 13. What’s about you?

11. How many people have you kissed?

I hope you can count that far!

12. What are you most afraid of?

Maybe you are afraid of spiders, snakes, or even of the dark?

13. What was the happiest moment of your life?

At least the happiest moment so far!

14. Do you think religion will always exist?

That’s a tricky one.

15. What would your dream house be like?

And how would the house be furnished? Dream together of your perfect house!

16. What is the most essential part of a friendship?

I think it’s honesty.

17. What is the story behind your first kiss?

I guess this story is pretty embarrassing.

18. What is the worst job you’ve ever had?

Did you hand out flyers or work in a telephone service? Tell each other about your worst job experiences!

19. What is the most interesting fact you know?

Tell it!

20. What would your perfect vacation look like?

Do you prefer a vacation on the beach or in the mountains?

21. Do you think of me when I am not around?

I hope yes!

21 dirty Questions to ask on a date night (18+)

This list is full of questions to spice up your date night. It doesn’t matter if you’re in a steady relationship with the other player or you’re just friends with benefits or even just started dating.

But if you’re looking for something serious or you just want to get to know the other person better, take a look at “21 Questions to ask your crush”. Because after these questions you maybe don’t know any new life stories, but you just want to rip each other’s clothes off. Pay attention, the following questions are 18+!

1. What is the wildest sexual thing you’ve ever done?

Yes, tell your naughty stories!

2. What is the most number of times you’ve done it in a row?

Puh… I hope you can count that far!

3. What are your thoughts on sex with me?

Yes, tell them your thoughts!

4. What turns you on?

The more honest you are here with one another, the less embarrassing conversations you will have to have later!

5. Do you remember what that first orgasm felt like?

Do you?

6. What is your favorite thing about a quickie?

You can also name more than one thing!

7. Have you ever had a sexy dream?

If yes, tell it!

8. What do you think about toys in the bedroom?

Maybe you’ll buy one together?

9. If I caught you masturbating would you carry on, ask for help or stop and pretend you weren’t?

10. Have you ever blindfolded or handcuffed your partner?

Are you into these things? Better be honest right away!

11. What is your favorite porn category?

Apparently, everyone watches porn.

12. Do you like BDSM?

Maybe you both into it?

13. What is your secret sexual fantasy?

Reveal your deepest secret!

14. What do you wear when you sleep?

Or maybe you are not wearing anything?

15. Would you describe yourself as naughty? Why do you say so?

Yes, justify your answer!

16. What was your best sexual experience?

Don’t rave about your exes too much.

17. What do you think of sexting?

Maybe you should try it out together right away?

18. What is the dirtiest thought you have ever had about a total stranger?

Tell it.

19. What is your favorite way to be seduced?

Another thing you could try out right away!

20. What is the weirdest thing you’ve thought about while touching yourself?

Hopefully, you won’t be telling each other gross stories now…

21. What do you do when you get horny in public?

Yes, what do you do?

21 questions to ask a girl

Do you have a girl in your life that you would like to get to know better? Ask her the following 21 questions!

1. Which song reminds you the most of your life?

And explain why!

2. Would you rather be rich or famous?

Yes, you can’t choose both!

3. If you could change anything about yourself what would it be?

No matter what she says, please just answer: You are perfect the way you are!

4. What’s a naughty fantasy you have about me?

Uh, do you also feel that it suddenly gets hot?

5. If you could choose one celebrity to be the mother of your child who would it be?

That’s a tricky one!

6. You only get 3 words to describe yourself – what are they?

That’s a really tough question.

7. What is your favorite joke?

Hopefully, she likes to tell jokes.

8. What is the dirtiest text you’ve ever sent or received?

Better think twice about whether you want to know it.

9. What is your morning ritual like?

Let her tell you everything about her mornings.

10. What do you think of threesomes?

Is it wise to ask a woman this question? I’m not sure.

11. If you found a briefcase of money on the street, would you keep it?

Maybe just a little of the money…

12. Has anything ever screwed up your birthday party?

Hopefully not!

13. What is your favorite oral sex technique?

A very intimate question.

14. What makes you special and unique?

It is always very exciting to find out what a person thinks of themselves.

15. Would you rather be a famous director or a famous actress?

I bet she would prefer being a famous actress.

16. What is the best decision you’ve ever made?

Maybe her best decision was to talk to you?

17. What is the worst advice someone has given you?

I bet it was a strange man who told her to smile.

18. Would you rather be Spongebob or be Patrick?

I would rather be Spongebob.

19. What do you think about marriage?

Phew, shit just got serious!

20. Which fictional character would you marry if you had the chance?

Be honest!

21. What are five things that you can not live without?

One of them is her mobile phone for sure.

21 questions to ask a guy

The following 21 questions are ideal to ask a guy of your choice. Of course, those 21 questions are also suitable to ask your boyfriend.

1. Which is more important, truth or happiness?

That’s a tricky one.

2. Do you find food places online and read reviews, or do you walk around until you find something?

This question says a lot about a person.

3. What makes you the angriest?

Hopefully, he’s not an aggressive person!

4. Clubbing or candlelight dinner?

Hm, maybe both?

5. What is the best thing I can do for you in bed?

Better listen carefully to her answer!

6. What is the length of your longest romantic relationship?

Of course, if you haven’t had a long-term relationship, that’s fine.

7. Have you ever hit the person you have been involved with?

Hopefully not! If she says yes, better run!

8. What do you think an orgy would be like?

I think it depends on the people participating, doesn’t it?

9. What does your ideal one-night stand look like?

Of course, not everyone has to like a one-night stand.

10. What is the silliest pick-up line or a phrase someone used on you to win your attention?

Is your name Earl Grey? Because you look like a hot-tea!

11. What was your worst first date?

Hopefully not this one?

12. In your opinion, what does it mean to be good in bed?

That’s a tricky question.

13. What is one habit that you find completely disgusting?

What do you think is more disgusting? Pick noses, bite nails, or something completely different?

14. Is there anything you won’t do in bed?

Be honest!

15. When and how did you find out that Santa isn’t real?

Hopefully, she doesn’t believe in Santa Claus anymore. Otherwise, it would be very embarrassing!

16. What attracts you to people?

That’s an exciting question.

17. What are your feelings towards open relationships?

There are actually many couples for whom an open relationship works very well. But a lot of people wouldn’t want that at all.

18. What would your perfect day look like?

Describe it!

19. Would you rather go on a fancy date or Netflix and chill?

Definitely Netflix and chill!

20. What are you most grateful for?

Stop for a minute and think about what you can be grateful for. Life is good, enjoy it!

21. What is your dream job, and why?

Maybe she even has her dream job already?

✍️  July 1, 2021

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