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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They had little hand held digital device for this back in the late 90’s, like a tomagatchi. It was super cool. My wife found one at the thrift store a few months ago and we played with it for a few days. It was able to guess correctly about 95% of the time.