This game combines an unfortunately too common theme in IF (waking up in an apartment after drinking and/or romantic affairs) with another too common theme (office bureaucracy) and another (wacky weirdness), but somehow without fully committing to any of them.
The ADRIFT parser is really poor here. "Two dollar bill" is recognized, but not 'two' or 'bill' or so on.
There was a bug partway through that kept the walkthrough from working for me.