Worst places, in my mind:
If she is the sporty type of girl: Take her to a Lamb of God concert, she will love that. Then for dessert make sure you take her to a LAN party with all of your Xbox friends!
If she is the 'emo', music loving girl: Take her to a golf tournament, then suprise with tickets to the Orioles vs Blue Jays game. She will just fall over in excitement.
If she is black: Take her to a klan rally, but make sure she is blind-folded and tell her she might be "participating" in the events that are happening at this special 'bonfire'
If she is a slut: Take her to the abortion clinic. Or the doctor's office; whichever one's closer.
That's about all that I can musker up right about now.