It all depends on the guy. In my opinion, your goal should be 1. to have fun and 2. to make the night memorable.
If he's a guy with a sense of humor that doesn't take himself too seriously, you could play a prank on him, like taking him to a strip club, but arranging for all the strippers to have his name fake tattooed on their collective asses and/or outer labia. Or, put an embarrassing childhood photo of him on some t-shirts and give them out to the strippers. Every dance would start with a pic of him peeing in the bathtub at age 4.
I have hundreds of these ideas running through my head. . . pretty much every day. PM me if you want some more.