Hi Troy,
did you give the tip to the waitress, as Romeo posted? If so, then do a little more pixelhunting near/around the bum and I'm shure, you'll find the office.
I'm not much further - only watched mr. Black and his office but Tom won't talk to him. I also can't get rid of the secretary (Tom won't put the worms from the nest on her or near her at the ground) and now I try to catch the cockroach, but can't find the cup. Can you give a hint where you found that, please?