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
How do you stump it?
I just played a few rounds. It correctly guessed, on its first try: