Despondent over his separation with his wife, the Mayor decides on a whim to take a road trip with Paul, leaving Mike in charge of New York City and scrambling to find out where they went.
The Mayor separates from his wife and moves in with Michael, much to Mike's chagrin. Meanwhile, designer Isaac Mizrahi helps the Mayor's office with a charity fashion show and gives Nikki a once-in-a-lifetime chance to strut the runway in one of his creations.
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.
On the personal front, Mike struggles with his ex-girlfriend, Carrie, who is desperate to bear his child (with or without his participation). At the office, he's playing peacemaker after the mayor's ill-chosen words split up a beloved band just before their reunion concert.
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.
Michael discovers that his new girlfriend, Gayley, is paying for law school by moonlighting as a stripper. Meantime, Claudia catches Paul in a lie, and Nikki plays mind games with Stuart.
A major snowstorm hits Manhattan, causing a chain reaction of mishaps at City Hall. Mike desperately tries to meet his longtime crush on her last night in the city; Paul accidentally offends the Mayor on the radio; Carter and Stuart are locked in the boiler room; and a nudist is on the loose in the Mayor's office.
For the Mayor's 50th birthday, Paul is determined to get his ""old friend"" George Stephanopoulos to attend the event; as Michael arranges for birthday wishes from David Letterman, Patrick Ewing, Al Michaels, Dan Dierdorf, Frank Gifford, Rosie O'Donnell, Larry King, and the cast of Rent. But in the midst of the planning, a scandal swirls about the Mayor's presumed affair with a staffer from the Governor's office.
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.
Mike butts heads with a hard-nosed new chief of staff appointee, Gabby Sanchez, who is unmoved by his best efforts to win her over. Meanwhile, Paul ponders taking his relationship with Claudia to the next level.
Michael is uncomfortable with his newly single status when he realizes he's actually on a date with new assistant district attorney Danielle Brinkman. Meantime, Paul meets the president of his fan club, Claudia Sacks, who has arranged the group's first meeting. And Carter and Stuart have a little too much to drink and end up in an awkward situation.
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.
Michael substitutes for the Mayor on a political talk show, facing off against Ashley on a hot-button issue. Meanwhile, Paul plays City Hall Santa while battling a terrible bout of the flu that is sweeping the office. And everyone finds themselves going to Carter for romantic advice.
Mike tries to appease the disgruntled Police Commissioner by honoring a beloved police dog who has recently died. But things go awry on the way to the funeral when Paul and Carter lose the canine's body. And Mike buys an air hockey table for the staff proving Stuart a very big talker.
When the Mayor's office competes against City Council in an annual Thanksgiving contest, the stakes are high, since the losers must croon a show tune in front of the press. James has trouble breaking up with a longtime girlfriend visiting from Wisconsin.
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.
Michael needs a favor from famed real estate developer Dan Donaldson, but the price Mike has to pay may not be worth it. In the meantime, Paul finds it hard to crow about the city's lowered crime rate, since he's just become a victim of a robbery-again. And Mike and Ashley can't agree on what show to watch when they're in bed.
Carter and Nikki plan a fake wedding to make a point about the mayor's stance on same-sex marriages. Meanwhile, Paul is a transformed man when the eye patch he wears after a minor injury gives him unprecedented self-confidence and sex appeal. And an unsatisfied Ashley considers leaving her new TV show for the newspaper again.
When Mayor Winston's nominee for the Public Schools Chancellor proves an embarrassment to the administration, James urges Mike to stick with the controversial candidate. In the meantime, Ashley considers a career in television on a roundtable show.
The former Mayor of New York is a constant critic of the current administration, and a plan to appease him has tragic consequences. Meanwhile, Michael and Ashley try to avoid their annoying new neighbors. And Nikki holds a contest among the men in the office to prove that none of them could ever be fathers.
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.
Michael and the Mayor work around the clock to negotiate an end to the garbage strike, which leaves Stuart in charge of the office, to everyone's dismay. And, though they just moved into a new apartment, life is so hectic that Ashley and Michael never get to see each other.
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 Flaherty and his team grapple with a garbage strike and a political gaffe by the Mayor who accidentally insults gays. In addition, Ashley questions Mike's commitment to their relationship when is nervous about moving in together.
