Damn he's good. I was thinking Audrey Hepburn and he guessed it, but it took him about 20 questions.
but what if you don't know all of the details and end up giving a few wrong answers?
You do have the buttons for "probably yes/no" and "I don't know" in there as well, so if you answer truthfully, and the database is accurate enough (not many other people screwed up) and large enough (to include who you're thinking of), he should be able to "guess" it correctly. Still, the program is nothing but a big database, so if you mislead it, intentionally or otherwise, he will either require more questions to make the connection to the right person, or end up providing a completely wrong answer.