Mike Flaherty has to juggle the interests of his conservative mayor boss and a gay activist whom the Mayor has unwittingly insulted. At home, Mike has to deal with his reporter girlfriend Ashley, when it finally dawns on him that she doesn't just sleep over but that she actually lives with him. To appease both Carter, by having his voice heard, and the mayor, by correcting his gaffe, Mike hires Carter as his new consultant of minority affairs.
The mayor's vocal wife causes Mike and the staff heartache as Winston and the staffers attend a dinner hosted by Catholic and Jewish leaders in New York City at which the mayor is being honored. Meanwhile, Paul is uptight over Ashley's latest reporting hot streak involving an internal audit at a Queens high school and Mike faces problems with his love life following his being named the Sexiest Man in New York.
Mike and Ashley's hectic schedules cause problems in their personal lives at home. Meanwhile, the garbage strike continues and as negotiations continue between the Mayor and the workers, Stuart is left in charge of the office while Mike keeps Winston in line.
A camera crew for a magazine films Mike and his staff performing their daily office duties and they each give their own spin on what goes on in City Hall every day. While this is going on, the reporter develops the hots for awkward speech writer James and Carter encourages the mayor to address the pressing issue of AIDS in New York City.
Winston, jealous of the old Mayor Garfield's likability factor which he just can't seem to obtain, wishes death on the man and within a couple of days, he gets his wish! Mike and the staff try to console the Mayor by telling him it's not his fault and that Garfield had a bad heart. Nikki bets that none of the men in the office have what it takes to be a dad.
Dr. Bronsteen, an old professor of James', is appointed the city's new School Commissioner by Winston, but it is later revealed by the press that he was caught on camera smoking pot at a 1971 Grateful Dead concert causing duress for Mike and disbelief for James. Ashley is offered a job reporting for a local TV station.
Ashley's job for New York's ABC affiliate isn't as fulfilling as her old one; Carter plans to marry Nikki to make a point to the Mayor on gay marriage. He believes that if two heterosexual people are allowed to marry no matter how close they are or how much they have in common, gays should be able to have the same luxury.
Paul's identity is stolen during a period where crime in the city is at its lowest rate in years. A famous developer signs onto a project for the Mayor's office and hopes for something in return: he suggests an unethical opportunity for Mike to inform the billionaire about the lowest bid for a construction contract he wants.
City Council's Lisa challenges Mike to a turkey cook-off on Thanksgiving to see who can feed more homeless people: the Mayor's office or City Council. Meanwhile, James looks for a way to break up with his girlfriend of seven years. To complicate things, Becky shows up to surprise her long-distance boyfriend for the holiday.
Mike attempts to appease the Police Commissioner by honoring a fallen hero: Bingo, the police dog. Things get out of hand, however, when Paul and Carter lose the dog's body after they're kicked out of a cab and Mike can't stall the service for Bingo any longer. Ashley ponders boundary issues when she overhears a message intended for Mike regarding the Bingo situation.
When the Mayor falls ill due to Paul spreading a nasty flu bug all around the office, Mike steps in for His Honor on the national TV show "Counterpoint." The best part is that his opponent happens to be his girlfriend, Ashley. Also, Carter has the staff coming to him for ridiculous dating and relationship advice. At the end, he thanks God that he's gay.
After Ashley Schaeffer leaves him for a better job in Los Angeles, Mike attempts to cover up by saying it was a mutual decision and that he gave her his approval to take the job. Mike later reaches his breaking point as he nearly strangles Stuart in a restaurant after he calls her a bitch and confesses to Nikki that he begged her to stay but she left anyway.
New Asst D.A. Danielle Brinkman, an old friend of Mike's, is eager to get re-acquainted, but out-of-sorts Mike finds it hard to date after his breakup with Ashley, despite her great looks & advances. Paul meets his fan club president.
Mike plans a star-studded party for the Mayor's 50th birthday, but tries to keep him away from Holly Cohen, Randall's romantic interest from the governor's office so that the Winston marriage doesn't suffer.
During a blizzard, an inept security guard pursues a nudist in City Hall; Mike's high school crush visits en route to Paris; Paul & Randall make gaffs during a radio broadcast; and Carter and Stuart get locked in the boiler room.
Randall is depressed after signing divorce papers. Claudia pursues Paul. So both men skip town for Miami, leaving the other staffers to cover for them. Stuart has a personality change due to his new girlfriend.