Dave and Busters FTW...casual, not to stuck up of a place, certainly not boring--there's always the movies if D&B falls through...

Ask your boss what this chick likes; they seem to know each other--

You could always go blind--as soon as she gets in the car--"So, what do you guys want to do?" That's worked for me in the past...

I say start w/ D&B, then maybe bar-hopping, or the local 'disco'...It really kind of depends on what this girl is like...ask your boss about it--nothing direct, just figure out where the girl wants to go, whether you want to go there or not; <---this WILL work

IDB?!?!<-----WTF? In Da Butt?