Tried a newer character to see how it coped, after one bad guess it got Leo from Anarchy Reigns. Only been guessed 10 times before too.
EDIT: I finally beat it, with HUnter X Hunter's Phinks. Also, it's very difficult to trick it with characters that look misleading in their description, as despite asking age in both of them, it guessed Leorio and Bisky from HxH with ease.