I just played a few rounds. It correctly guessed, on its first try:
Twilight Sparkle (it really rubbed my nose in that one – “Is your character associated with My Little Pony?” [Yes] “Does your character have a horn?” [Yes] “Does your character have a pet dragon?” [Yes] “Does your character like to read books?” [Bro just admit you know who it is])
Spyro the Dragon
Spyro’s sidekick Sparks the Dragonfly
Honey the Cat, an unused playable character hidden in the game files from the little known arcade game Sonic the Fighters
Jewel the Beetle, a character who only appears in the most recent Sonic the Hedgehog comic books, and even then infrequently
My first try took 36 questions. It’s first guess was wrong.
2nd attempt:
I picked Sparks from Sealab.
3rd attempt The Noid, guessed on second try.
4th attempt the Lady in the Radiator, guessed on third try.
This is fun!
5th attempt stumped it again with Walter Kramitz from Big Trouble! It got close with Officer Slater from Superbad.
So pick a minor character in an obscure story.
How do you stump it?
I just played a few rounds. It correctly guessed, on its first try: