Herman has to decide whether to take advantage of Connie's break-up with Jay to express his own feelings, or provide her with a shoulder to cry on.

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.

During a party for Mr. Bracken, Herman drinks a bit too much and gets in over his head when he has to give a speech praising his boss.

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.

Herman, who is 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's relationship with his brother Stan has never been too good, and when Stan and his fiancee Jaclyn visit, things get even worse when Jaclyn starts hitting on Herman.

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.

Herman accidentally spills some secrets that his co-workers told him to the others, getting him into trouble with everyone.

Herman gets a new lease on life after almost falling to his death, and sets out to establish a new world record for working continuously until he drops.

Mr. Bracken wants Herman to escort his daughter Susan around, but takes a dim view of things when the two become romantically involved.

After buying a stolen computer, Herman is stricken with guilt and goes to absurd lengths to try and return it.

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.

Bracken calls Herman into his office to inform him that he is having a heart attack, and leaves Herman in charge of the office in his absence. Meanwhile, Herman's brother comes to town and introduces him to his new fiancee, who makes a secret pass at Herman.

Herman fills out an evaluation form for Mr Bracken which included some negative remarks. After realizing that his evaluation might have serious consequences on Bracken's career, Herman goes about trying to set things right.

Herman goes skydiving with Mr. Crawford and Jay and writes an article about his experience skydiving.

Herman begins dating attractive model Jennifer, but soon begins to question his good fortune.

Victoria, a powerful female executive at Waterton, wants Herman to become her assistant editor. It soon transpires that Victoria wants Herman for more then that, however.

Crawford insists on the research department going to the Bahamas for a self-awareness seminar...which everyone discovers is an all-nude seminar.

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.

When Herman's apartment is robbed, Crawford convinces him to buy a gun for self-defense, but he winds up accidentally shooting Crawford in the chest.

Herman and Jay go undercover to get a story on a princess, but Herman soon falls in love with her.

Another one of the Brooks brood come visiting when Herman's little sister Suzie arrives in New York. Already over-protective of Suzie, Herman's anxieties get even worse when she and Jay sleep together.