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!
This is an ancient project. At some point in the past, I went to this site and it was intentionally broken by its developers, such that it would only guess from a small subset of possible targets, and if your character was outside of that, it would act like it knew the answer, but wouldn't say unless you gave them money.
I don't know if that's changed since then, because that experience ruined it for me, and I won't be going back there.
I think that it was fucking with me. I chose Aladdin and it really didn’t seem like it was going to get it until question 19 “does your character like flying on carpets?”
I've noticed that sometimes he gets very close quickly but then drifts away to other questions that seem less relevant. But I don't mind this myself.
The excitement stays, whether he will guess what I think about or not - I don't mind answering 60 questions or even 100.
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.