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.

When Laurie accepts Mike's proposal, he begins to worry that they are too different. Meanwhile, Paul struggles to get the courage to propose to Claudia, and various staff members fantasize about what their life would be like if they married Mike.

Mike and Caitlin return from Paris as a couple. Caitlin wants more than a physical relationship, so Mike bets her that he can resist her for a week, while tries to break his willpower. The mayor falls in love with Rags after filming an animal rights commercial with him.

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.

It's damage control time when the Mayor's inept new sign-language interpreter inadvertently offends the deaf community, and Michael rushes to appease one of its leaders, Sarah Edelman. Meantime, Paul is worried that Claudia wants to move in permanently.

While jogging in the park to support the Mayor's fitness initiative, Carter is apprehended by the police, who mistake him for a mugger. To Carter's chagrin, Michael wants to downplay the incident for political reasons, while Carter wants to publicize his own outrage. Meanwhile, Paul becomes paranoid that he himself is a racist; and James struggles to pull off a successful date with the new supply girl, Katie.

The Mayor agrees to a mock election with a popular disc jockey. Meanwhile, the women in the office compete for the affections of the water delivery man.

As Mike's 30th birthday approaches, he is reminded of a promise he made to his high-school sweetheart, Renee Miller, long ago: If they were both still single by the time Mike turned 30, they'd reunite at the top of the Empire State Building on his birthday. Both of them keep their promise, with surprising results. Meanwhile, the Mayor wonders if his nephew is gay.

When Mike begins dating Lisa, a writer from the soap opera ""All My Children,"" he starts to see their dating life echoed on episodes of the popular serial: A new hunk named Mick Flannery joins ""All My Children"" and woos the resident vixen, Gillian--until she reveals their bedroom secrets to Edmund. Meanwhile, Stuart plays gay in order to get dates with beautiful women.

Mike must choose between protecting his mom, Macy, and protecting the Mayor, when he tries to spin the Mayor out of a new scandal--His Honor's alibi would reveal that he spent the night with Macy instead of a prostitute. Meanwhile, Paul is sued and goes to The People's Court to defend his case.

The Mayor's free-thinking daughter, Meg, with whom he has a somewhat strained relationship, puts the ""bare"" in bareback when she disrupts a rally with hansom-carriage drivers in Central Park to draw attention to her animal rights stance--and not coincidentally, herself. Meantime, the gang tries to reunite a needy Paul with ex-girlfriend Claudia, but he's smitten with his new pen-pal.

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.

Mike tries to dissuade the Mayor from joining a club for males only. Stuart joins the City Hall all-female reading group. Paul schools James in playing three-card monty.

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.