If you do not have a new acquaintance or romantic interest, tailor your questions to suit getting to know someone more deeply.
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.
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 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?”
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.
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.
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.
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.
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.
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.
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.
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.
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.
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?”
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 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?”
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.
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?”
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?”
