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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. 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. 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. 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?" 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. 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. 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.
Choose someone to answer questions. Identify what you want to know. Write a list of questions. Consider the setting. Show respect. Identify off-limits questions. Set rules for how to pass on a question.