iMessage games can be a fun way to connect with long-distance friends or your partner. Whether you’re bored and simply looking to pass the time or you want to get to someone new, 20 questions is always a classic.

Getting to play it over messages is a blessing. With the changing dynamics where people have gotten used to doing more and more things online, iMessage games are becoming quite the norm. Unlike other online games, you don’t all have to play at a designated time. You can play your turn at your discretion when you have the time.

So, you can expand a match over several hours. You can also continue using other apps on your iPhone while playing a game. Here’s how you can play the classic game 20 questions on iMessage.

Rules for the Game

If you’ve never played 20 questions in real life before, here’s a crash course for you. 20 Questions is a guessing game. In a 2 player game, one player sets a word that the other has to guess in – you guessed it right – 20 questions or less.

The word can be anything, but you can also choose to define the categories to which it can belong. Common categories include People, Places, Animals, Things. It’s usually a noun. Let’s call this person the “question master”.

The other person asks a question that the question master can only answer in Yes/ No. So, the burden of structuring the question properly falls on the second player. The question should be such which can be answered clearly as a Yes/ No.

The question should also be framed in a way that offers insights into what the object could be. When asking further questions, frame them in a way that they build further on the information provided by the previous questions.

At any time, the player can also frame the question in a way that allows them to guess the mystery object.

Tips for Playing the Game

Guessing a word starting with no information can be overwhelming. So, you must ask the questions in a manner that helps you inch closer to the finish line.

Some common questions include:

  • Is it alive? This question is widely hailed as the pefect question to start with. It helps you determine whether the object in question is animate or inanimate. If the answer is Yes, you can eliminate all inanimate objects from your guesses. The next questions depending on this information can be Is it a Person? or Is it an animal? But if the answer is No, you can proceed accordingly. A great question in this context for more insight can be Is it manmade?
  • Is it bigger than a lunchbox? Other popular questions revolve around size. Lunchbox is just an example. The motive is to try to estimate the size of the object. Don’t ask vague questions like Is it big? or Is it small? Keep them specific. Follow up the question with another size reference, like Is it bigger than a horse if the answer is yes, or Can it fit in my pocket? if the answer is no.
  • If it’s a person or a place, the questions like Is it real or Is it fictional can further help you.
  • At any point, if you’re certain you’ve guessed it correctly, you can frame your guess as a question, like Is it a wallet? You win if the answer is Yes. If the answer is No, you can continue guessing.

Hopefully, the above examples will prove useful in illuminating how the game is played. Ask your questions in a way that helps you narrow the category further. Don’t just throw around wild guesses.

If the person guesses the object in 20 questions or less, they get a point. Otherwise, the question master gets the point.

When playing with 3 or more players, one player starts by asking a question. They can continue asking questions until they get a Yes in return. If they get a No, it’s the next person’s turn to ask questions and the cycle goes on until someone guesses correctly or they run out of their 20 questions.

Get 20 Questions on iMessage

You can get iMessage games from the Appstore. But if you go on to search for it, you’ll come empty-handed. It’s because 20 questions is a part of the popular app GamePigeon which is the go-to app for playing several games for iMessage.

Open a conversation in iMessage and tap the ‘App Store’ icon.

Then, go to the search option and look for ‘GamePigeon’. Tap the ‘Get’ option to add it to the iMessage app drawer.

Playing 20 Questions over iMessage

Open the chat with whom you want to play the game. You need 2 or more people to play the game. To open the game, go to the app drawer and tap the option for ‘GamePigeon’.

The complete roster of games in the app will appear. Tap the option for ’20 Questions’.

Then, enter the secret word that you want the other person to guess and tap the ‘Play’ button to load the game in the message box.

Tap ‘Send’ to send the game invitation to the other person.

The other person will type a question and send it to you.

You’ll get 4 options to respond: ‘Yes’, ‘No’, ‘Sometimes’, and ‘You’ve guessed it’. Tap the option accordingly. The addition of ‘Sometimes’ is not often used in traditional games, but it doesn’t change the game as the questions still have to be framed in a certain way. You can’t change your answer once you tap it, so pay attention while playing.

The game will continue for 20 questions. If they guess it correctly at any time, tap ‘You’ve guessed it’ to end the game. In this situation, you’ll lose.

Example for illustration purpose.

If they can’t guess it in 20 questions, the game will automatically end declaring you the winner. The other person will automatically see the word at the end, so if you cheat, they’ll know.


Playing 20 Questions on iMessage with the GamePigeon app is extremely easy. In fact, for the person guessing the word, it has an additional advantage. The game has a record of all the questions asked so you can scroll anytime to see them. In a traditional game, you have to rely on your memory. You can even hop on an audio or video call to make the experience better.