I tried confusing it by thinking about Hilary Duff then Lizzie McGuire & flip flopping back & forth. The last question before it guessed the right answer was "Has you character ever been in Lizzie McGuire?"
I was thinking of Jessica Biel and it guessed Katherine Heigl
EDIT: It guessed Christina Applegate on the second try. Not Jessica Biel failing to be a Web Genius draw in addition to failing being a box office draw