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I was able to beat that guy using extremely obscure game characters.
I used Toorum from Legend of Grimrock (a game I doubt you've heard of and a character that doesn't even appear in the game outside of notes) and Zahra from Prince of Persia: The Forgotten Sands.
Everyone else he completely nailed after some tries.
Bastard guessed my "Unkindled One", aka protagonist from Dark Souls 3.
I beat him using Exo (GG MF's onboard AI).
Guessed Azir correct
After 50 questions...
He couldn't even come close.
Shenhua from Shenmue
He kept guessing some weeb garbage. :D
Is your character female? yes Is your character able to cast spells? yes Does your character have an evil laugh? yes Is your character from League of Legends? yes Is your character mean? no Does your character use guns? no
Lux, the Lady of Luminosity.
I think you had me the moment I clicked yes on an evil laugh.
I did manage to beat him with Nanaa Mihgo. That's my GURL!
He guessed Kalista correctly and never even mentioned LoL