To get a story, Herman goes undercover as a woman and discovers a few things about Heddy and what she goes through.
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.
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 then 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.
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't help himself and reverts to type.
Motivational speaker Dick Van Adams inspires Herman...to become a success while stepping on his friends.
Herman's sister Suzie 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.
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 of Brady Bunch memoirs, 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.
A movie star, who's playing the role of an adventuresome fact-checker in his next film, researches his part by tagging along with Herman.
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."
Crawford's girlfriend Stephanie dumps him and goes after..Herman, who finds himself in a bind.
After getting refused for an important writing job, Herman goes up to the roof and ends up trapped with a suicidal nutjob, Bob, 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 and Heddy decided to give into their feelings and start dating, but a series of interruptions keep them from consummating their relationship.
Herman decides to give it all up during a tropical vacation and buy a local bar on the island.
The "head" characters go into overdrive when Herman tries to get a good night's sleep the night before a high-pressure meeting.
Herman finds himself attracted to Lil the copy girl, but she doesn't return his feelings.
Herman breaks up with his newest girlfriend Sarah, but sees her a little later and tries to get back together with her.
Herman becomes involved with Sandra Clayton, 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.