If you know the 20 questions -social (party) game, this is kinda the computer version of that. He can guess a character, and object or an animal. If he cannot guess what’s on your mind, you can teach it to him!
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This was the thing some 10 or 15 years ago.
Its abilities are uncanny.
Edit: It got these right:
I’m still able to consistently win with anything more obscure than this.