Herman becomes involved with Julia Campbell, a rather opinionated woman who immediately clashes with Jay over his misogynist views.

When Herman's one-time girlfriend (and Bracken's daughter) Susan returns to town and wants to start up their relationship again, Herman has to choose between her and his new girlfriend Elizabeth.

Elizabeth becomes suspicious when she finds out Herman is working undercover as a dating show contestant, believing he might be tempted by other women.

Herman and Elizabeth decide to move in together, which prompts no end of arguments over shared space, priorities, etc. Finally they decide to break up.

The office workers go on a trip to the Bahamas - Herman has to deal with Elizabeth, who happens to be on board, while Louise gets to indulge her long-time infatuation for Davy Jones of the Monkees.