Understanding the Game
Choose someone to answer questions. The purpose of the game is to ask someone (solo, or a member of a group) 21 questions, all of which must be answered honestly. Although it can be played with friends you’ve had for a while, it is usually best to choose someone you don’t know as well, or someone you want to get to know on a deeper level. If you do not have a new acquaintance or romantic interest, tailor your questions to suit getting to know someone more deeply.
Identify what you want to know. Once you’ve chosen a person to ask questions of, identify what it is you want to know about them. If you’ve chosen a friend, do you want to know more about their background, or are you more interested in their future plans? If you’ve chosen a romantic partner, do you want to know about their dating history, or do you want to know how they feel about your relationship? If you are playing in a group, you can decide as a group what types of questions to ask. This can be tailored to each target, or there can be an overall theme for the game.
Write a list of questions. There are two ways to play: the first involves people asking whatever questions come to mind, and asking them at random. The second has the pair (or group) come up with a set list of questions which are then posed to each person. Writing a list beforehand is the easier choice, as everyone knows what they will be asked, and will likely agree to answer. Asking at random may be the more entertaining choice, but is also at higher risk of getting too personal or inappropriate.
Consider the setting. If you decide to play this game with strangers or acquaintances you meet in a specific setting, you may want to take that setting into consideration when forming some or all of your questions. If meeting with members of a book club or writer's group, you might ask questions like, “What is your favorite book?” or “If you could be any fictional character from any book, who would you be?” If meeting with a church group, consider questions such as, “What is your favorite Bible verse/story?” or “When did you first develop an interest in religion?” If meeting someone new at the grand opening of a coffee shop, consider questions like “What is your favorite snack to enjoy with coffee?” or “Would you rather give up coffee for a month or stop showering for a week?”
Show respect. Although many of the people playing 21 Questions use is as a method to ask probing or otherwise inappropriate questions, respect the privacy of the person being asked questions--particularly in a group of people. If they want to sidestep something, or answer in vague terms, allow them to do so. The golden rule is a great thing to keep in mind when playing this game. Treat the target the same way you’d like to be treated during your turn as a target.
Identify off-limits questions. There are some questions that should not be asked in any circumstance. Before you begin the game, identify any questions that might be too inconsiderate, thoughtless, or crude to ask. These questions can include broad categories such as sex and intimacy, or can be specific questions, such as, “Have you ever committed a crime?” You can also create guidelines about the sort of questions being asked based by theme. For instance, if playing 21 Questions at a church youth group, you might indicate that at least half of the questions must be religious in nature.
Set rules for how to pass on a question. There may be a question that is just too probing or intimate for someone to answer. To safeguard against people getting upset, make a rule before starting the game for these instances. A simple rule could be that a target can pass on a question, but must then be asked a question in its place, or that the target can pass on a question, but will forfeit their turn to ask the next target a question.
Playing In a Group
Determine the “target” sequence. In a group, there are going to be multiple targets and multiple people asking questions, so you need to choose a fair method for deciding who goes first, second, third, and so on. Rolling a die is a great way to choose a sequence. Each person rolls, and the person with the lowest roll goes first, followed by the second lowest, and so forth. You can also do something like “Rock, Paper, Scissors” to determine who will go first, and do it again before each new game. You can also go in a circle when deciding the order of targets. Once the first person has gone, the person to their left is the next target, and that cycle continues until everyone has had a turn.
Take turns asking questions. Now that the target and sequence have been decided upon, each member of the group should take a turn asking the target questions. You can divvy up the questions based on the number of people in the group (a group of 3 askers could have 7 questions each, for instance), or you can go in a circle and have each person ask one question at a time. If there is a number of people unable to divide evenly into 21, sit in a circle and have someone start the questions. The next round, the person to their left can start the questions, and continue in this manner until everyone has had a chance to ask first.
Move on to the next target. Once all 21 questions have been asked, either move on to the next target in the predetermined sequence, or take a minute to determine a new target using Rock, Paper, Scissors, or a coin flip.
Playing With Two People
Agree upon boundaries before and after the game. When you are playing with only two people, you may be asking more personal or intimate questions than you would in a group. For this reason, you should both agree upon boundaries for before the game (questions that are off limits), as well as after the game (such as, “We cannot treat each other differently after answering the questions”). This game can injure friendships and relationships quickly, if proper precautions are not taken. Do not ask questions you do not genuinely want the answer to. If you are not sure whether a question is appropriate, simply ask, and give your playing partner a chance to either accept the question or request another one.
Choose who will go first. The simplest way to choose the first target when only two people are present is to flip a coin. Once you’ve flipped your coin, understand that you must take a turn after the first target has completed their questions. Do not use this game as a means to gather information and refuse to play after the target has finished. This game should always be played on equal footing.
Ask questions. Ask the target 21 questions, using the previously agreed-upon list of off-limits questions as a guide. If you are playing with a friend, ask questions that tell you more about your friend, your friendship, and your friend’s preferences. If you are playing with a romantic partner, ask questions about their life, background, your relationship, and their needs. This game can be great for new couples who want to know more about each other quickly and easily. This game is also wonderful for breaking the ice with a new acquaintance, and should focus on basic, getting-to-know-you questions or silly questions rather than deep or intimate ones.
Take your turn. Once you have finished asking questions, take your turn! Submit yourself to the same questions you’ve asked, or answer entirely new questions. Give the new asker the same courtesy they gave you and answer questions honestly and succinctly. If you do not feel comfortable answering a question, be gracious in asking for a new question. The game is supposed to be fun, and should not cause anger or emotional injury.
Asking Questions
Cover the basics. To start out, ask basic questions, such as someone’s favorite color, their first celebrity crush, or where they grew up. You’ll want to ask small, easy questions at first to build trust between the asker(s) and target. Ask “favorites” questions, such as, “What was your favorite age?” “What is your favorite place to visit?” “What was your favorite part of school?” “What is your favorite way to travel?” Ask “what if” questions. You can ask, “What if you could visit any time period in the past?” “What if you could fly?” “What if you had fingers on your feet, and toes on your hands?”
Build upon the questions you’ve already asked. Once you’ve built some groundwork with basic questions, you can ask more personal questions, or you can simply build off of the questions you’ve already asked and the answers you’ve received. To build off of answers you’ve received, take an answer and phrase a question around it, such as, “Your greatest fear is spiders, so what would you do if you moved into a house with a spider infestation?” To build to more personal questions, you can say something like, “The person you’d most like to meet with in the past or present is Susan B. Anthony. Why is she so important to you?”
Ask questions that require creative answers. Some questions are going to be simple (e.g. “What is your favorite movie and why?”), while others are going to require a little bit of thought. Even if you are asking serious questions, ask the target questions that require some creativity or ingenuity to answer. Ask silly questions such as, “Do hair stylists go to other stylists or do they cut their own hair?” or “If an ambulance accidentally injures someone on its way to save someone else, who do the paramedics choose to save?” You can ask serious questions, too, such as: “If the world was ending and you had to save one person, who would you save?” or “If your relationship was starting to go sour, what would you do to try to save it?”
Ask about family and backgrounds. Whether you playing with a friend or a romantic partner, you could always stand to learn about other people’s family and backgrounds. Asking about family can help you get to know your playing partner’s habits and traditions, and asking about their background can lend insight into any cultural differences or interesting ideas they may have. For family, ask questions such as, “Who raised you?” “Was your family close growing up?” “Did you have any special traditions during holidays?” For background, you can ask questions such as, “Do you know where your ancestors are originally from?” “Did you celebrate any special holidays growing up?” When dealing with family and backgrounds, remember to exercise sensitivity; both are very personal topics and require kindness and open-mindedness.
Ask about past romances and interests. Questions about past romances have the potential to be silly, entertaining, or informative. When deciding what type of past romance questions to ask, consider the tone of the game. Are you playing to deepen your connection to your playing partner, or are you playing to escape boredom on a weekend? If you want to develop a deeper connection with your playing partner, you can ask questions such as “Who was your first kiss?” “What is the best date you’ve ever been on and why was it the best?” “Do you have any fantasies?” If you are asking silly questions, you can ask thing such as, “What was your most awkward kiss?” “Have you ever sneezed in a love interest’s face?” “How long should you wait before passing gas in front of your significant other?”
Ask about goals and aspirations. When asking about goals and aspirations, you must also be somewhat delicate, as you don’t want to laugh or make light of other people’s dreams. When asking these types of questions, you can keep things light-hearted, but avoid mocking your playing partner’s answers. Light-hearted questions can include: “What did you want to be when you were 5?” “Where do you see yourself in 10 years?” “Do you hope to be famous one day?” More serious goal questions can include questions such as: “What do you want more than anything else in the world?” “If you could do anything, and money and living were already taken care of, what would you do and why?”
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