^ your heart was in the right place but i have to tell you as a friend the punchline was more what we might've expected from panzur. i'm no expert but unless you're norm macdonald, having to explain the punchline usually spells disaster.
and hitting girls with the fat hammer usually works but she's a lot more teflon/jaded than most due to her line of work, plus not that fat, so you gotta come from another direction. maybe go with a science fiction or middle earth angle next time re: the face.
all else fails- read a few cosmo's, take the quizzes, find out what gets under their skin this spring.