I made another try, here's my results.
Quote from Cave Story - Failed First Guess
Caesar from New Vegas - Failed First Guess
Brucie from Grand Theft Auto - Failed Second Guess
Crazy Dave from Plants Vs Zombies - Failed Third Guess
Meat Boy from Super Meat Boy - Failed First Guess
Bandage Girl from Super Meat Boy - Failed Second Guess
Calendar Man from Batman - Failed Second Guess
Sander Cohen from Bioshock - Victory!
Edit: More
Ema from Phoenix Wright - Failed First Guess
Detective Gumshoe from Phoenix Wright - Failed Third Guess (I thought this one was close but then they asked if he was made by Capcom. Fuck)
Larry from Phoenix Wright - Failed Second Guess (Guess what game I've been playing a lot of?)
Terezi from Homestuck - Faile First Guess (He was on to me super quick with this one, I knew I was fucked at "Do they wear glasses?")
Caliborn from Homestuck - Failed First Guess (Clearly Homestuck is not the route to go here)
Keith Brown, SNP Politician - Victory!
Paul Elam, Runner of A Voice for Men - Victory!
Me - Failed First Guess
Jon Ronson, Journalist and Writer - Victory!
Louis Theroux - Failed Second Guess
My Character from some fan-fic I wrote - Victory! Obviously. Though it did guess Xbox 360 avatar, and I think it deserves a round of applause for that.