Herman and friends swap memories of their first meeting. 

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 tries to win back an ex-date after seeing her out with another guy.

Herman falls for the woman who repairs the copier, but she can't duplicate the feelings he has for her.

The "head" characters go into overdrive when Herman tries to get a good night's sleep the night before a high-pressure meeting.

Mr. Crawford announces a company retreat to the Caribbean. Herman decides to give it all up and buy a local bar on the island.

Herman and Heddy decided to give into their feelings and start dating, but a series of interruptions keep them from consummating their relationship.

Herman tries to transform his girlfriend into a sex kitten.

Herman gets trapped on the roof with a suicidal man when the office building catches fire.

Crawford's girlfriend Stephanie dumps him and goes after Herman, who finds himself in a bind.

Herman agrees to pose as Heddy's husband to impress her old friend and rival. 

A movie star whose next role is as a fact checker makes Herman his role model. 

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.

Herman's vacation is disrupted when Louise and Jay blow in, dragging their relationship baggage with them. 

Herman's sister Suzy 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.

A motivational seminar has Herman suddenly climbing the ladder of success, but he steps on his friends, especially Jay, on his way up.

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 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.

Herman falls for new assistant editor Heather but she has a hairy situation. Louise is alone and Herman sets her up with Jay.

Herman learns his new girlfriend is Crawford's daughter.

Bracken's niece neglects mailroom duties to become a dancer.

To get a story, Herman goes undercover as a woman and discovers a few things about Heddy and what she goes through.