My first one that I stumped him with was: Sandra Bullock (I had just read an article about her on Yahoo News and she was all I could think of) He thought: Penelope Cruz.
My second one, I thought of my favorite actor ever: Nicholas Cage and he guessed him!
My third one I thought of that robust cook with the nasally voice who uses like 4 pounds of butter in her cooking, Paula Deen, and he thought of a black guy, I can't remember who but I was laughing out loud!
-----Added 10/26/2009 at 05:21:02-----
haha, I just tried Paula Deen again to see if it would tell me who the guy was, but of course he GUESSED her this time!
He asked, "Does your character wear bras?"
My answer, "I sure as hell hope so!!!" *barf*
-----Added 10/26/2009 at 05:22:59-----
I just tried ALF, and he guessed ALF!!