When Mike's new girlfriend, Laurie, bonds with Nikki, Mike must compete with his own staffer for Laurie's attention and free time. Meanwhile, Paul's bombshell mom dazzles his coworkers when she visits the office, and the Mayor is in a mess over an X-rated video.

Michael tries to dissuade the Mayor from a relationship with Jennifer, a much younger woman. However, as Mike deals with his own relationship troubles, Jennifer makes a pass at him. Meanwhile, Paul is acting as Michael's assistant, and enjoying it so much that he can't bring himself to hire the best candidate for the job, Stacy Paterno.

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's mom, Macy, is visiting for a week and she and the Mayor hit it off better than Mike ever imagined, or feared. Meanwhile, Nikki dates Steve, a ventriloquist whose dummy, Mr. Bungle, is more romantic (and talkative) than Steve. And Stacy and Stuart scheme to get Hank, an elderly security guard, his job back after he accidentally shoots Paul.

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.

Mike struggles to make the children of New York believe again after the Mayor tells them that there is no Santa.

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 usually indomitable Mike can't cope at the office because of upsetting news he's unwilling to share--his doctor suspects Mike has prostate cancer. The timing couldn't be worse, since the Mayor needs Mike to help write his newest book, so Mike brings in best-selling author Donald Trump to advise the Mayor on writing. Meanwhile, a chair-snatching bureaucrat is terrorizing the staffers. (Warning: Donald Trump is in this episode.)

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.

Stacey's grandmother puts a curse on Mike after he convinces her to move out, into Manhattan. The Mayor is concerned he's losing his hearing. And there's a void in Stuart's life after he is moved upstairs and is not allowed to make sarcastic comments anymore.

Faced with the prospect of spending Valentine's Day alone for the first time in eighteen years, Mike is thrilled when old flame Laurie steps back into his life. But he doesn't know what to do when she discovers a ring Mike was holding for Paul, and assumes it's for her. Meanwhile, Paul plans to propose to Claudia.

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 suggests the staff undergo drug testing to demonstrate the mayor's new anti-drug campaign. But after he accidentally gets high while visiting some Native Americans, he risks failing the drug test that he initiated.

The Pope is visiting New York City, leading to spiritual revitalizations for Mike and the mayor. Carter fixes Nikki up with a friend of his. And Paul's turtle is loose in City Hall.

The staff prepares for Paul and Claudia's bachelor and bachelorette parties as the city prepares to unveil a new statue that it commissioned. The girls play ""I Never...."". Paul's party is in the office because the Mayor can't go to strip clubs. The new statue, called ""The Bird,"" is, you guessed it.... The girls think a visiting priest is a stripper because of a prank pulled by Stuart. James and Carter go to the hardware store and it is robbed with them in it. Mike is trapped in the store too, after he goes checking for James and Carter. Stacy sends the guys the male stripper Stuart canceled for the girls.

A female magician performs at City Hall and Mike asks her out. Stuart and Carter purchase a bar. After sleeping together and telling him she's not interested in a long-term relationship, the magician says ""I love you"" to Mike. Stuart wants to make the bar a gay bar. Mike has trouble breaking up with his girlfriend. The bar is closed because it was missing a permit, leaving Stuart and Carter penniless. Mike finally tells his girlfriend how he feels and they break up.

Stuart lobbies to become Carter's roommate. After Carter's apartment is robbed, he must let Stuart stay. A rat on the loose in City Hall wreaks havoc on the staff and Paul's cat.

The Mayor has a stuttering problem. And Mike has a big problem when he promises to coordinate Paul and Claudia's wedding but discovers that the church is also booked for a funeral at the same time.