I've drilled my helmet. But only because my wife wasn't in town.
Hey-oh!
But seriously folks, I have drilled a hole in my helmet for the rivet that holds the microphone/headphone connector, and it's really no big deal. Jim has it mostly right. Put some blue painter's tape or masking tape on the helmet, mark it with a pen, then drill a small pilot hole. Be careful to pull back the inner soft shell/lining so that you don't drill through that too; you might even be able to remove it depending on your helmet. You don't need a step drill, just regular small twist bits will be sufficient. The plastic on most helmets is pretty plastic (not to confuse a noun with an adjective) so you don't really need to worry about cracking it, you're not really putting a lot of pressure on the helmet so long as you start with a small pilot hole.
Good luck, and please tip your waitstaff, they work hard for the money.
Pat Mulry, TARP Racing #67
Mandatory disclaimer: all opinions expressed are mine alone & not those of 24HOL, its mgmt, sponsors, etc.