Herman is sued by a woman he gave CPR to when he accidentally cracked her ribs, while Jay learns to deal with his sexual addiction.
Herman's former girlfriend Rebecca wants to renew their relationship...for the purposes of getting him to help in artificially conceiving a child.
Herman tries to halt Heddy's wedding because he realizes that she does not love her fiance, and because he realizes that he still has feelings for her himself, and if he doesn't act right away, he may never have another opportunity again.
No good deed goes unpunished for Herman once more when he hires Louise's friend as an office intern, and she turns around and sues him for sexual harassment.
When even Herman can't find a date for a desperate Mr. Bracken, he turns to Jay for help, with dubious results.
Waterton's sudden death creates a scramble for power, and to save everyone's job, Herman decides to join forces with Crawford - who then involves Herman in a secret campaing to eliminate the competition for control of the company.
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.
Herman must overcome his fear of public speaking, when he is forced to give a speech on the topic of Research in the 90's, at a company meeting.
Herman and Heddy are stranded on Christmas at Louise's parents' place, and the Fitzers drive Louise crazy.
Herman messes things up yet again and sets Louise up with John, who turns out to be a married man...but Louise doesn't figure it out until she is deeply in love with him.
To save Crawford's butt, the gang has to pull an all-nighter to get him out of a jam. Herman and Heddy, Bracken and Crawford, and Louise and Jay end up pairing up and each learn something new about the other on an intimate personal level as they struggle to meet the deadline.
When Louise and Heddy strike back at their obnoxious new boss, Herman gets caught in the middle.
Still recovering from his break-up with Elizabeth, Herman gets set up on a blind date, while the rest of the gang play poker.
When Herman hosts a Valentine Day's party, everyone gets lucky...except him.
Herman ends up sleeping with the aptly-named Eve, and his ""Head"" personalities get a visit from God, or Herman's image of him...as Leslie Nielsen.
Jay gets a visit from his ex-fiance, who stole his heart, and left him standing at the altar seven years earlier. After talking and spending some time with her, Jay's old feelings for her are rekindled, but the question is: will she break his heart again? When Herman wonders exactly that, he and Jay's friendship is in danger.
Herman gets a visit from another family member when his his newly retired father visits looking for some company and the chance to rebond with his sun. but Herman doesn't have the time to spend with him.
Herman manages to get Heddy fired for screwing up a report assignment, and then has to go the distance to get her job back.
It's time for a near-end-of-scene flashback episode to save money, as Herman recalls his adventures in New York while deciding whether to stay where he is or go back to his hometown in Ohio to accept a new job.
Herman parties with heavy-metal rocker Lita Ford, jeopardizing a harmonious relationship with his girlfriend.
When Herman starts dating new girlfriend Carin, he initially runs up against tough resistance from her son Brad. Ironically, Herman manages to win Brad over and the two become best buddies...much to Carin's dismay.