Newly divorced Mr. Crawford gets Mr. Bracken as his wing-man. Herman demands to write and Mr. Crawford offers him an assignment to go undercover as a woman. Something is bothering Heddy and she opens up to Herman in drag.
It's the Research Association dinner. Mr. Bracken is doing the speech and everybody has to attend. Herman falls for new assistant editor Heather but she has a hairy situation. Louise is alone and Herman sets her up with Jay.
There's an office pool of when Jay and Louise will have sex. Herman's sis Suzy Brooks wants to be a writer. Louise grows jealous over Jay and Suzy's past affair. Herman is going after a writing job but Suzy also wants in.
It's Herman's 3 year anniversary in the Research department. Movie star Thomas Alan Edwards wants to observe him for a role. Edwards starts copying and annoying him. Edwards gives him his hotel room which is filled with his sycophants.
Heddy's college friend Heather Brookshire visits. Herman has a date with Tawni. When Heddy finds out that Heather married poor for love, Heddy competes with her by pretending to be with our pathetic loser Herman.