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I played with him five times.

 

He guessed Ilya from Fate/Stay Night on his first go.

 

He didn't guess Johnny from FF7

 

He guessed Cirno from Touhou on his third guess

 

He didn't guess Karks from Moetan

 

He guessed Chris-chan on his first guess (I answered "partially" to that question)

 

EDIT:

 

I thought of Josef "the dungeon keeper" Fritzl and he got that right first time as well :3