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21 Questions Game Great, Dirty, Funny, Random Questions to Ask

21 questions game is pretty straightforward. You need 2 or more people to play this game. Basically, one player asks 21 questions and the other one answers them. Additionally, you can make your own rules. For example, you can split the questions in half and take turns. It’s a great way to get to know someone.

There are no right or wrong answers to this game, the game unveils a lot about your opinion, mindset, views and how you think about life and relation. If played right and answered truthfully, this game can turn out to be a great way to build a strong bond by knowing the other person better.

However, an important point to note here is that while asking the question it’s important that you select the question wisely the question should be shortlisted depending on the kind of relationship you share with the others.

Here we’ve got a huge list of questions you can ask a guy/girl in order to get to know the other person. We also have a great collection of Ice Breaker Questions and Would You Rather Questions.

Here I have categorized 21 questions in each of the four genres, The Good/Clean 21 Questions, The Funny/Witty 21 Questions, The Romantic or Dirty 21 Questions and Additional 80+ Questions. Choose from these or come up with your own question and let this game do wonders.


  1. What is your favorite food?
  2. How do you spend your weekend? Do you like to sleep or party hard?
  3. Which song can you listen over and over again without getting bored?
  4. How do you want your dream home to look like?
  5. If given an option, would you choose a holiday at the beach or in the mountains?
  6. Have you ever cheated in the exams?
  7. Have you ever played the role of opposite gender in the school drama?
  8. What makes you happy?
  9. What is that one thing which makes you lose your temper?
  10. Have you ever failed in your school?
  11. When was the first time you bunked your school?
  12. When was the first time you had tasted the alcohol?
  13. What is your dream job?
  14. Are you a mama’s boy/girl?
  15. What is the most daring thing you have ever done?
  16. If you had the power to turn someone into an animal, who would you like to turn and into what?
  17. If you are made the president of the United States, what would be the first thing that you will do?
  18. Are you fetish about something? If yes, what is it?
  19. Which comic character do you love the most?
  20. If given a chance to meet 3 most famous people on the earth, who would it be, answer in order of preference.
  21. If you could change one bad quality of yours, what would it be?


  1. Have you ever wanted to travel back in time, if yes, in which era you would want to go?
  2. If you get a chance to be reincarnated, whom would you like to be born like?
  3. Have you ever wished to have a superpower, if so, what superpower you would like to have?
  4. If God grants you three wishes, what would you ask for?
  5. If granted a foreign citizenship, which country would you choose?
  6. Have you ever fought in public? If so, what was the reason for the same
  7. If this world is supposed to end tomorrow and you have only one day, how would you spend that day?
  8. Would you like to be famous or rich?
  9. If asked, which would describe you the best what would it be?
  10. Are you a hashtag person, who likes everything posted on Instagram?
  11. Have you ever been on a blind date?
  12. Which song describes your life the best?
  13. If you get to change your name today, what name would you like to have?
  14. Do you like to share everything on social media or do you believe that there is a limit to it?
  15. Are you a fun loving person or the one who likes to go by the books?
  16. Have you ever doped?
  17. How did you spend your first salary?
  18. If you could bring back one dead person who would it be and why?
  19. Have you ever watched a movie more than once just because you could not understand it?
  20. Can you spend an entire day without phone and internet? If yes, what would you do?
  21. For an all expensed paid trip, which place would you like to visit?


  1. Have you ever had a crush on your best friend but never told him/her about it?
  2. Have you ever had an extra-marital affair?
  3. Are you okay with relation outside marriage?
  4. Sex or romance which is more important for a relationship?
  5. Can a marriage survive without sex?
  6. What qualities don’t you want in your life partner?
  7. Live-in relation or marriage, what is your take on relation?
  8. What is your weirdest sexual fantasy and have you ever followed it or still waiting for it?
  9. How to you want your dream date to be like?
  10. How many relations have you had till now?
  11. At what age did you lose your virginity and with whom?
  12. If stuck in a lift with Kim Kardashian, what would you do?
  13. When did you first have a crush?
  14. Have you ever had sex under the stars?
  15. What is the one thing which you can never forget about your first night?
  16. Have you ever had a one-night stand with a stranger?
  17. What if your ex and your wife/husband turn out to be acquaintances? How would you react?
  18. What attracts you in the opposite sex?
  19. Have you ever cheated on your partner?
  20. If you get to have a destination wedding, which destination would you choose?
  21. On a scale of 1 to 5, 1 being the worst and 5 being the best, how would you rate your partner and yourself?


1. Would you rather leave your hometown and never be able to return again, or stay in your hometown but never be able to leave? This will tell you if he or she has a sense of adventure or never wants to leave home.

2. If you were an animal, what would you be and why? A way to find out if he or she likes animals and what their preferences are.

3. What is your favorite item of clothing? Is he or she too serious or too casual?

4. What do you think about marriage? This one will tell you if he or she is looking for the same thing you are.

5. How would you describe yourself? This tells you how the other person sees themselves.

6. Sneaking into a second movie: super-wrong or harmless fun? This just might give you some insight into their idea of law abiding.

7. What did you want to be when you were young? Childhood dreams may reflect several things about him or her, personality, family values, or ideologies.

8. Are you superstitious? A good way to find out if they believe in only what they can confirm with their senses (touch, vision, hear, taste, and smell).

9. Where would you go for your dream holiday? This may give you a sense of things they like to do, hiking, historical tours, beaches, fishing, scuba diving etc.

10. What’s something everyone else loves that you secretly find overrated? How come? Just as an example, cheeseburgers because they are vegan or social media because it’s a waste of time.

11. What is your favorite movie? This will let you know if you like the same kind of movies, action, drama, comedy.

12. What is your favorite type of music? Again this will tell you if you like the same kind of music, smooth jazz, classic rock, country.

13. If you could be anyone else for a day, who would you choose? This will tell you what they are interested in, fame, inventing things, teaching others, helping others such as doctors or EMTs, firemen, policemen.

14. What is your morning ritual like? This will tell you if they plan or go with the flow, do they brew their own coffee or buy a cup on the way?

15. Have you ever been arrested? How many times? This is going to tell you if they made a mistake once or they continually break the law. Our advice if it’s the latter, break it off and don’t look back.

16. What do you think of public displays of affection? Is this something that they find embarrassing or just bad etiquette?

17. If you won the lottery, what would you do with your money? This could tell you if they are greedy, to giving, or a moderate who will save some, use some, and give some.

18. Are you addicted to anything? This may not be drugs or alcohol or gambling either, there are many forms of addiction.

19. What’s your favorite time of the year? Why? Summer, winter, etc. this can tell you what kind of weather and weather related activities they like.

20. What is your favorite holiday? Maybe it’s Halloween, Thanksgiving or Christmas, be sure to ask why. The answer might surprise you.

21. What’s your favorite and least favorite color? This will help you know what they like and you won’t have to wonder when purchasing a gift for them.

22. Would you mind if your partner made more money than you? This could be an insight into whether they are old fashioned or modern when it comes to working and who brings in the most money

23. How many jobs have you had? Why? Pay attention to this, it will tell you if they work to better themselves or if they might have commitment issues. If they were bored, commitment could be an issue, if it was better hours or better money or both, they are working to improve themselves.

24. If you’re having a bad day, how can I cheer you up? Will just being there help or will you need something more.

25. Do you like children? This is another of those that will tell you if you want the same things or not.

26. If you were stranded on an island and allowed one luxury item, what would it be? A glimpse at what they really think is important when it comes to luxuries or material items.

27. What is the wackiest gift you have ever received or given someone? This will give you an insight into their sense of humor.

28. What are you most afraid of? The willingness of an answer on this shows you they have some amount of trust in you.

29. Are there any causes you strongly believe in? Some insight into things that matter to them as well as possible ideology.

30. Do you have any guilty pleasures? Things we don’t readily admit too often tell us the most about a person.

31. Who’s your hero? This is an interesting one as some will choose a family member while others choose a character from a movie or book. Ask why they chose that person or persona for a real glimpse into the way they think.

32. What would you do if you had one day left to live? This allows you to see what or who is truly important to them in their life.

33. Do you collect anything? Many people collect things, the question is how much? How obsessed? Are they a hoarder of this item?

34. What was the last book you read? Do they have a passion for reading, or was it in high school?

35. How much time do you spend on social networking in a week? This is a good one; do they live in the real world or spend it on social media on the computer?

36. How did your last relationship end? Remember every break up has two sides.

37. Do you believe in soul mates? Some people do some people don’t until they actually meet theirs.

38. How important is your family to you? This will tell you what kind of relationship he or she has with their family.

39. Have you been tested for STDs/HIV? Would you be willing to go in for testing again before we get more involved? This is an important one, if they are not willing to get tested, you may want to rethink getting more involved. Even if they say they never had sex, there are other ways of contracting some of these diseases. Blood transfusions, shared needles.

40. Do you believe in God? You will get an idea of if they are religious or not.

41. What was the happiest moment of your life? Don’t let them get away with just saying meeting you. If they say that ask for the happiest moment of life before that.

42. How old were you when you started dating? This will let you see if they have been dating for a long period of time and if they have really decided on what they want out of a relationship or not.

43. How do you cope with stress? This is also a good one, we all deal with stress differently, some exercise, some meditate, some hold it inside until they erupt.

44. What is your favorite way of spending time with me? This could be slightly revealing, do they want you all to themselves in a possessive way or would they be happy sharing you with family and friends. If they seem possessive, don’t hang around.

45. Do you have any bad habits I should know about? Drugs, alcohol, gambling, and well you get the idea.

46. What do you consider the five biggest strengths of your personality? This will tell you how they see themselves.

47. Have your ever driven drunk or even slightly buzzed? You shouldn’t drink and drive so the next question is will you do it again? If they admit they would drive buzzed, you don’t want to ride with them.

48. Do you fall for a person fast? If you have been on a date or two and they start talking marriage, that is fast and you may wish to slow that down.

49. What did you do during the summers when you were growing up? Camping with family, summer camp, swimming at the Y tells you a little a bit about the way they grew up.

50. Are you competitive? This will tell you if they see everything as a competition they need to win

51. Clubbing or candlelight dinner? This tells you if they prefer lots of people or alone time with you.

52. What’s the worst thing you’ve ever done? This can tell you a little about their morals.

53. How would you like to be remembered? This can tell you how they really wish to live a life full of honesty and good or do wish to achieve a fortune or fame at any cost.

54. Do you like tattoos and body piercing? This allows you to glimpse into their personal preferences, there is no right or wrong answer here unless you have tattoos or body piercings that they cannot accept about you.

55. What are your life goals? A glimpse of how they see themselves in life and what they wish to achieve.

56. If you found a briefcase of money on the street, would you keep it? This lets you see if they are honest or dishonest.

57. When was the last time you felt really proud of yourself? You should be able to tell if they are extremely prideful or maybe they lack belief in their own worth.

58. What’s the length of your longest romantic relationship? This one can tell you a couple of things, first do they fall in and out of love easily and second are they afraid of commitment.

59. Are you impulsive or do you think first? While being impulsive can be fun, it can also lead to disastrous financial problems if they are too impulsive when making purchases.

60. Have you ever hit the person you have been involved with? This will tell you how they handle anger, stress, and what they use as a way to resolve it.

61. What’s your philosophy in life? This can tell you what they take seriously and don’t take seriously. Are they planners or just go with the flow.

62. Which personality traits do you want your partner to have? Which of these are an absolute must? This can tell you what they are looking for in a mate.

63. Would you rather live in a large urban city, a small town or in the countryside? Why? This will tell you if they are a city person or not, or if they wish to leave the country and try the city.

64. Can you dance? Do you like dancing? This is going to tell you if you should plan a night of dancing or not. It could also lead to the possible taking of dance classes together so give it some thought.

65. If you could have a new talent or gift, what would it be? You might want to ask why when you get the answer it could be telling as to what the talent or gift would be used for.

66. Are you an introvert or an extrovert? You can see how they will be at a party, shy and a wall flower or out there talking to everyone possibly being the life of the party.

67. Do you believe in monogamy? This is a good one, are you going to be their sole relationship or will there be someone else while they are seeing you.

68. Do you have siblings? If so please tell me about them. This will give you an idea of what kind of relationship they have with siblings if they have any.

69. What would you change about yourself if you could? This is going to let you in on what they dislike about themselves. At that point, you might want to ask why, as they may not see the way others do.

70. How do you feel about divorce? Is it the first choice or last resort? This will tell you if they are willing to try marriage counseling and couples therapy to save their marriage first or go straight for divorce.

71. How often do you spend time with your parents? This is going to allow you to know how important their family is to them.

72. Which was the worst phase in your life? This could be telling as to their teens or even early twenties and where they were emotionally and mentally.

73. What is the nicest or worst thing you did for a very good friend? This can show you how they treat their friends and people that they care about.

74. What do you value most in a friendship? This is going to tell you what they value in a partner as well, after all most good lasting relationships start with friendship first.

75. Do you judge a book by its cover? This is going to allow you to understand how they see people, do they get to know them first before passing judgement or are they quick to judge.

76. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why? This question is interesting; do they live life or just go through the motions? Most of us do not think that tomorrow or the next day may be the last day for us and did we accomplish what we should have, did we treat people with love and kindness. Think of the song “Live like you were dying” if you don’t know the song, look up the lyrics, it’s actually quite meaningful.

77. What would you do if you were stranded on an island and there was nothing to eat? This can tell you just how resourceful they are and if they give up easily.

78. Do you believe in karma? Call it Karma or the golden rule, the question is do they believe that you reap what you sew? It’s an interesting question.

79. When was the last time you cried and why? This will tell you if they are overly emotional or maybe they hold back their feelings some.

80. What roles do love and affection play in your life? This is a good question as it can give you a glimpse into their idea of what is important in their life at this point in time. Are they actively looking for love or is it a situation where life is good where I am right now but if love were to come along, I’m ready for it type thing.

81. Are you an optimist or a pessimist? This will allow you to know how they look at life as a whole if it is answered truthfully.

82. Do you think life is fair? An interesting question but could show you an insight into their ideology and outlook on life.

83. What, if anything, is too serious to be joked about? This is actually a good question as it might give insight into something they find offensive for a personal reason, maybe they had a family who committed suicide or battled weight issues. Things involving family and very close friends, effect people differently and leave certain issues with them emotionally, mentally, and on their soul.

84. If we were to have kids what faith would you wish them to be raised in yours or mine (if you come from different faiths)? This is a question you need to talk about before marriage and an important one. This also allows you to know how serious the other is about their faith.

85. Do you have a lot of drama or negativity in your life? If you don’t want to have drama in your life or relationship then you need to discuss ways to avoid it and not create it if it is a factor.

86. Where do I fit in with your priorities? This may seem like we have already covered it and in a roundabout way maybe we have, but this point blank sets the stages to see just where their priorities lay and this is important. Are you a priority or is it their job first, their friends, fun, and then you. You need to figure out where exactly their priorities lie and are they in tune with your own, especially if you want to have a real relationship with this person.

87. What defines beauty for you? This will be insightful, do they see beauty as an outward or inward beauty or a combination of both and in which way.

88. How would you handle one or the other of us being offered a dream job but having to move in order to take it? This is a good question and again goes along with priorities. Are you a priority in their life? Are they a priority in your life and you might want to add on to that question to include children and having to move.

89. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet? This could give insight on if they have difficulty conveying their feelings to people that they love.

Remember these questions can help you get to know each other if you answer truthfully and honestly.

However, you can never truly know someone, unless you spend time together doing everyday things, having coffee together and sharing the Sunday paper, shopping, eating in or out in a balanced amount.

I hope these questions were of great help for you to get started with 21 Questions game. If you liked them, please do leave your comments below.

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Written by Naveen

Entrepreneur | Web Developer | SEO Analyst | Animator


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