Oh wow, this is funny, I beat it thinking of Discord. I think I threw it off by thinking of a male MLP character. it seemed to be way off until the last question (it kept asking things like, "is it on Nickeloden?" "Is it related to Loony Toons?" but the last question was "is he brown" which made me think he got it at first, but then he guessed Dr.Whooves. Which is still funny since he never guessed if it was MLP related. It did naturally get it though after 26 questions.
Then I managed it again thinking of Abed from Community. The best bit is that it ended up guessing Troy the first time, but again it guessed Abed after 25 questions.
Tripping him up after only 20 questions still counts as a win, right? It's waaaaaaaay harder to actually have him be completely clueless about what you think. I think I've only managed that once.
Also, I'm somewhat impressed it got SCP-682. It looked like I was gonna trip it up, but it somehow managed it out of nowhere.