Mike and Nikki struggle with taking their relationship to the next level, i.e. sex. Stacy runs a phony psychic hotline on Paul. And the rest of the staff participates in a stakeout to demonstrate the city's new police technology.

Mike and Caitlin have sex. The staff works damage control but Mike ultimately fires himself to save everybody else. The staff says their goodbyes at the bar. Caitlin promises Mike that she's not going anywhere. Mike says goodbye to the mayor and walks out of City Hall for the last time. Six weeks later, Mike turns up as an environmental lobbyist in DC.

Caitlin takes a trip down memory lane and realizes that she and Charlie met years before and that he was the reason why she lost what might have been the best relationship of her life. Flashback to a preppy and conservative Caitlin and a cool, life-of-the-party Charlie at an old college bash. The flashback makes Caitlin realize that her current boyfriend, Tom, might not be right for her, and she ends up kissing Charlie! Meanwhile, the Mayor bartends at a fundraiser at which Paul is trying to pick up a woman, and the woman's friend has fallen for Carter, who is gay.

Caitlin is confused by the kiss she and Charlie shared and seeks the advice of a therapist. Meanwhile, the Mayor buys the staff palm phones which enable Charlie to accidentally eavesdrop on Caitlin's session. He decides to try to fulfill Caitlin's fantasies, which in turn prompts her to decide between Charlie and her current boyfriend, Tom. Paul appears on a controversial radio talk show with Carter feeding him answers.

Mike discusses his attempts to have sex with Caitlin with his new therapist. Nikki's new boyfriend is too likable. Caitlin isn't in the mood when Mike is. A reporter accuses the mayor of being involved in organized crime; Nikki's boyfriend turns out to be a mobster who has been getting the office staff to do favors for him. Mike weighs giving his friends up, but ultimately throws himself on his sword and takes all blame.

When Mike is named Sexiest Man in New York by ""Manhattan"" magazine, he has difficulty living up to the notoriety at home. In the meantime, the staff must deal with Mayor Winston's problematic wife during an important dinner.

Michael allows a TV crew into the office for a profile on himself, and one of his quotes lands him in hot water with Ashley. In the meantime, Carter goes behind Michael's back to get the Mayor to green-light a controversial project.

An opinionated school janitor becomes ""Mayor for a Day"" when he wins an essay contest intended for schoolchildren. Meanwhile, the Mayor wants to change his image.

The office rallies to lift Mike's spirits after his break-up with Ashley, but he resists their best efforts. That is, until he decides he needs a friend and reaches out to Nikki in the middle of her date with the perfect man. And Paul sets a New Year's resolution to be less gullible.

It's Valentine's Day, and Carter's old flame Spence wants to meet with him. Meantime, Mike goes on a date from hell with a beautiful friend of Nikki's, and Paul's romantic evening with Claudia becomes unforgettable for all the wrong reasons.

The men in the office find love-or rather, lust-is in the air, causing more than a few problems. And Nikki wonders whether her new heartthrob, George, is a struggling writer or an untalented mooch.

A champagne filled New Year's celebration at the Mayor's mansion gets out of control, resulting in more than a little embarrassment the next day, especially for Mike and Nikki. On the big night, Nikki's date, Jay, two-times her and a protective Mike not only gets even--he gets Nikki. Meanwhile, Stuart is undone over the death of his family cat and Stacy makes James question his own virility.

The staff prepares for the mayor's bid for re-election announcement. Mike becomes a hero when he saves a runaway baby carriage, but the reality of the situation isn't what it seems. Carter adopts his family's 19-year-old dog. And, Paul teaches Stacy how to get a sick day without being sick.

After Mike's picture with model Heidi Klum is in the tabloids, people assume he's dating her. But, he soon is after she asks him out. As a result, Nikki reveals to Carter that she has a secret crush on Mike. And The Mayor can't stop laughing at VERY inappropriate times.

The Mayor brings an abandoned baby to City Hall. Mike's old girlfriends voice opinions about him. The Mayor sends James to see a psychiatrist for him, concerning his sexual problems. Mike wants to adopt the baby. The Mayor takes Viagra to help him out. Mike's interview with the social worker doesn't go very well. Nikki prepares to tell Mike about her crush on him, but can't quite get the words out.

After the Mayor is photographed throwing a baseball ""like a girl,"" Mike tries to give him a more macho image. But when a teenage girl mugs the mayor, Mike and Paul; Mike's got more damage control than even he can handle. Meanwhile, Stuart loses his heart to Deirdre, a woman who's just as detestable as he is.

The Mayor is disturbed by a campaign commercial by his opponent, starring his ex-wife. Mike plans the City Hall Thanksgiving, scheduled to be televised live throughout New York City, with the Mayor's father scheduled to attend. At the dinner, the Mayor blows up at his father on live TV. Meanwhile, Stacy mistakes Stuart for her boyfriend in the dark and lays a big wet one on him, making her think twice about her feelings for him.

The staff prepares for the Mayor's costume ball. Stuart tries to break up with Deidre. And after Mike sets Stacy up with a councilman to get his vote, she likes the set-up as the councilman plays the hero.

Carter and Stuart plan to spend Christmas together. Mike must baby-sit a smart monkey that will be given to the city zoo as a gift from Ghana. The staff prepares the City Hall greeting card. Carter and Stuart meet two old men from their building who mirror themselves in 30 years.

When the mayor starts to worry about becoming the object of a violent attack, a videotape showing Mike apparently leaving him in the line of ""gunfire"" damages their relationship. Meanwhile, Nikki sees Mike in an entirely different light after her viewing of the same tape reveals he was trying to protect her. And, Arthur wants to propose to Nikki, but puts his relationship with her at risk by confiding in Stuart.

Mike and Nikki decide to keep their relationship a secret. Stacy's Aunt Marie visits. Deidre files sexual harassment charges against Stuart after he dumps her. Carter is talking about himself in the third person. Marie tries to seduce James. Stuart is close to being fired. Deidre offers to drop the charges for sex, immediately, with Mike. Thanks to the building's new security cameras, Deidre is exposed. The mayor finds himself growing attracted to Janelle, and the two kiss while discussing the sexual harassment case.

Mike's political mentor is preparing to visit with the mayor preparing to appoint him head of the city's millennium project. Marie is still in town and messing around with James. The mayor and Janelle plan a get-together. Owen has changed a little over the years and believes he is the Messiah. After Carter puts Rags in Paul's care, Paul accidentally kills the ailing dog. Owen brings Rags back to life with a touch.

A feuding Carter and Stuart become friends with the other's ex, just for spite.

It's Nikki and Mike's four-month anniversary. James is still the only person who knows, but he wants to tell. Stuart takes Carter's job for a day, helping the mayor deal with various ethnic groups. James develops a rash from keeping the secret. Mike prepares for a magazine interview, but during the interview, the reporter's focus shifts to Carter. Stuart enlists Stacy's help with the ethnic groups. James spills the beans.

Mike is tested when Nikki is out sick and the mayor hires his ex, Heidi Klum, to help publicize the new animal rights campaign. Meanwhile, the mayor and Paul try to inject some humor into their press conferences. When Mike accidentally tells Nikki that even though Heidi came onto him, he had feelings for her and still turned her down, she walks out.