I assume you are using version 4 right? So you are stuck at chapter 8? have you tried female clothes as a waiter? did Bob give you a "female" uniform? Have you gotten the fresh supplements directly from Bob?
Yes, version 4, have the todo list, done the female waiter uniform, even did the stall at the bar. I have no new dialogue with bob, i already use the female gym clothes.
As I've guessed the issue was with my save file. I started a new game amd rushed my progress back to chapter 8 and then i was able to progress to the end of the current version.
