Herman becomes enmeshed in a web of lies of his own making when Meredith, a former classmate-turned-woman reporter, shows up to do a "Where are they now?" story on Herman's less-than-stellar life.
When Louise's newest relationship goes sour, Herman ends up comforting her and Louise gets the wrong idea; Herman has to figure out a way to let her down gently.
In this play on the movie Fatal Attraction, Herman has a one-night stand with a woman, Yvonne (Megan Mullally), who turns out to be more than a little obsessive...
Herman, who has been tired of being considered "sweet", seeks to be more red-blooded. When an executive vice president of the company is sexually harassing Heddy, Herman punches him out.
Herman is left in charge of the office after Bracken informs him that he is having a heart attack. Meanwhile, Herman's brother Stan visits with his fiancee, Jaclyn. Herman and Stan's already fraught relationship gets complicated when Jaclyn starts hitting on Herman.
NOTE: Jason Bernard eventually succumbed to a real-life heart attack four years later in 1996.
While working late to finish a project, Herman eavesdrops on Heddy and her date. After finding out he is married, Heddy turns to Herman for solace. They eventually wind up sleeping together in Bracken's office, but don't know how to handle the affair the next morning.
A coworker of Herman's is killed in an elevator accident that nearly killed Herman as well. Because Herman was the last man he had spoken with, the coworker's spirit reappears inside Herman's head and convinces the quartet not to be forgotten as he was. Herman seeks to break a new world record for most work done in one sitting, which starts impacting not only his office performance, but encouraging Louise to try something. It is incumbent on Mr. Bracken to teach Herman about the meaning of remembrance and living life.
Herman meets famous Pulitzer-winning writer, Russell Boswell, who Herman admires because of his no-holds-barred pursuit of the corrupt. But when Herman becomes involved in Boswell's own not-so-ethical investigation of a Senator, he has second thoughts.
Mr. Bracken is being considered for a promotion, and Herman is asked to evaluate Bracken's performance in his current position. Inside Herman's head, Genius suggests that there is always room for improvement, and that performance reports ought not to be too negative or too positive, so Herman writes that Bracken can be gruff on the job. When Herman learns that even such small remark could be censure to doom Bracken's career, he goes to great lengths to stop Mr. Waterton from reviewing it.
Victoria, a powerful female executive at Waterton, wants Herman to become her assistant editor. It soon transpires that Victoria wants Herman for more than that, however.
Herman and the others decide to help Mr. Bracken quit smoking by all resolving to give up one bad habit of their own in a show of team support. Unfortunately, the result is that everyone is going crazy, just in time for a corporate consultant's review of team performance and downsizing.
Louise decides it's time to lose her virginity, and starts checking out her prospects. When there are plenty of men willing to sleep with her, but not treat her as a woman and a human being, Herman tries to convince Louise virginity can be of great value.
When Mr. Bracken and his wife break up, Herman sympathetically invites him to stay at his apartment - hilarity ensues as the two become the "Odd Couple" of sorts, and Herman and Louise set out to reunite Bracken and his wife.
Another one of the Brooks brood come visiting when Herman's little sister Suzie (Jennifer Aniston) arrives in New York. Already over-protective of Suzie, Herman's anxieties get even worse when she and Jay sleep together.
Herman tries to halt Heddy's wedding because he realizes that she does not love her fiance, and he realizes that his feelings for her continue; if he does not act right away, he may never have another opportunity.
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.
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 campaign to eliminate the competition for control of the company.
Herman becomes involved with Elizabeth (played by 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 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.
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. God has paid the quartet a visit on account of Herman's Uncle Wally about to undergo major surgery, although He is not happy about what is transgressing with Eve. Leslie Nielsen guest stars as God.
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 newly-retired father visits looking for some company and the chance to rebond with his son. When Herman is able to be with his father, Dad decides to come to Herman...by getting a token job at Waterton Publishing.
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 gets invited to an after concert party in the hotel suite of rock star Lita Ford, but winds up cheating on the girl he is dating with the rock star. Lita Ford guest stars.
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.
Herman encourages Bracken's niece Rene to become a Fly Girl (i.e., a dancer on "In Living Color"); Mr. Bracken isn't particularly happy about Rene's career choice or Herman's involvement. The Fly Girls (Laurie Ann Gibson, Jossie Harris, Deidre Lang, Lisa Thompson and Masako Willis) guest star.
Herman wants to break up with his new girlfriend Ellen, who convinces him to meet her father; things take a turn for the worse when he discovers her father is none other than his boss at Waterton, Mr. Crawford.
In his eternal quest for the perfect girlfriend, Herman dates Heather, but it turns out she's a tad too hairy for his tastes. Meanwhile, Jay and Louise begin to wonder if they're attracted to each other. Morey Amsterdam and Rose Marie guest star.
Herman's neighbor in the upstairs apartment drops dead after the two of them had a shouting match. Compounding Herman's problems, Heddy decides to take the apartment after her current boyfriend kicks her out of the apartment he's paying for.
When Jay decides to turn a new leaf and give up his old womanizing ways, Herman tries to get Louise to go on a date with him, but Jay just can not help himself and reverts to type.
Herman's sister Suzie (Jennifer Aniston) comes back to town and manages to aggravate both Herman (she plans to become a writer) and Louise (since she previously dated Jay). Appropriately, the "brain" characters get a new and annoying addition when Jealousy joins their group. Bobcat Goldthwait guest stars as Jealousy.
While taking a vacation Herman becomes involved with Aurora, a beautiful model. Nothing ever works out for him as usual, though, when Jay and Louise show up with their own rocky relationship and both looking to friend Herman for help and support.
Herman gets to work with Maureen McCormick as she writes a book on contraception, getting to fulfill his long-time crush on the actress. Unfortunately, he and Jay almost come to blows when a jealous Jay confesses to a similar crush. Maureen McCormick guest stars.
When Heddy's old rival Heather arrives in town, Heddy asks Herman to pose as her husband to impress the woman. Meanwhile, Mr. Bracken works on his musical, "Deuteronomy."
After getting refused for an important writing job, Herman goes up to the roof and ends up trapped with a suicidal nutjob, Bob (Gilbert Gottfried), when a fire breaks out.
Herman's new girlfriend Lauren is everything he could want, personality-wise, but as always Herman isn't happy as he obsesses over playmate Miss February.
Herman becomes involved with Sandra Clayton (Michelle Phillips), who is running for the Senate, but when the tabloids get hold of their relationship Sandra has second thoughts.
Herman is hit by a taxi in an accident and as he lies in a coma his staff friends each remember Herman as they first met him, with each brain character filling in for the emotion the friend first saw Herman acting out.
References
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