Add
Private Notes
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.
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 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
While acting as the Mayor's divorce lawyer, Michael is attracted to his opponent, Laurie Parres. Meanwhile, the press thinks Paul has suffered a nervous breakdown, so Michael enlists a psychiatrist, Dr. Benjamin, to pronounce Paul sane. But his plans go awry when Dr. Benjamin unexpectedly commits Paul to an institution.
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.
Mike finds out that his new girlfriend, Laurie, isn't looking for commitment, which he thinks is great-- at first. Meanwhile, James has a mysterious new hobby, which Stuart and Carter are determined to uncover. And Janelle asks for a raise with surprising results.
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.
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.
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.
Mike prepares to have sex with Heidi Klum for the first time. After ""it"", Heidi asks Mike to keep their relationship a secret. James receives his Aunt Sarah's ashes in the mail; his Aunt Sarah was a cow. Mike daydreams while making a statement to the press and accidentally reveals his relationship with Heidi; she breaks up with him. Paul's new fan creates problems for Aunt Sarah (take a wild guess).
Carter, Nikki and Mike go deer hunting in a fundraising attempt. While Mike is gone, Stuart becomes Stacy's boss for the day. And, with Claudia's help, Paul campaigns for a raise.
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.
Mike discovers that his childhood pal, Nate Scott, has more in common with Carter than meets the eye, and finds it difficult to deal with this revelation. Meanwhile, Paul instructs Stacy in the finer art of being a cheapskate.
Paul has moved to Harlem and is annoying Carter and Janelle because he thinks that he's black. The Mayor is preparing to run the Olympic torch around City Hall, but can't because the Nigerian speed walker supposed to deliver the torch to him has disappeared, lost in the city. Mike struggles with the fact that he can't live without his job, while trying to take a vacation. Nikki finds a ringer to pose as her boyfriend, for them to have dinner with Mike. Stacy spills the beans to Mike about Nikki's feelings for him.
Stacy's staying with Carter and Stuart while her apartment is fumigated. Her partying cramps their style. Trying to outdo NASCAR driver Jeff Gordon and NBA player Jayson Williams, the Mayor promises his kidney to a young boy. Unfortunately, his doesn't match--but Mike's does. Meanwhile, Mike's playing the jealousy game with Nikki and promises to donate his kidney to the boy in hopes that she'll break up with Arthur for him. But when she offers him a chance to speak up about his feelings, he's anesthetized for his surgery and can't say anything.
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.
Mike can't stop thinking about Nikki. Nikki is ready to take the next step with Arthur, but Mike is worried about that. Paul unwittingly has an affair because Stuart needs him to. Stacy dates a job-obsessed cabbie just because he looks good. James inadvertently causes a taxi driver strike, which interferes with Arthur getting to the airport. You see, if Arthur misses a plane, he and Nikki will have sex.
The mayor submits a personal ad in a newspaper as the rest of the office men prepare for the mayor's annual male bachelor charity auction. Mike chooses to spend some extra city money on a futuristic new bathroom for City Hall. The new bathroom is insensitive to overweight people. The mayor asks Paul for advice on how to approach a woman. Stacy teaches James how to model so that he can garner more money than Mike in the big auction. Mike puts on a fat suit to appease the head of the overweight person's commission. Stuart's sister is in town but no one has seen her.
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 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 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.
Nikki wants to make her relationship public knowledge. The mayor prepares to appear on ""Politically Incorrect."" Carter is dating a gay boxer. Paul becomes addicted to Stacy's aunt's meatball subs. The mayor accidentally outs his relationship with Janelle while on TV. Nikki and Mike fight after he's not ready to expose their relationship yet.
Mike makes the staff work on Oscar Sunday due to a screw-up of Paul's. The staff reminisces about their favorite movie moments to pass the time.
Mike agrees to donate sperm for Paul and Claudia, not realizing what Paul forgot to tell him. A City Hall tour guide is harassing Stacy. James has been commissioned to write a piece for ""Sassy.""
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.
The staff pesters Nikki for details about her sex life with Mike. James asks Mike to invest his life savings in an Internet company, but when Mike holds off on investing, the stock goes up several points, and Mike must find a way to make the money back. Meanwhile, the mayor has an action figure made of himself but unfortunately, they're all anatomically correct.
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.
Mike tries to convince Nikki that nothing is going on between himself and Heidi Klum. The mayor doesn't understand that Janelle wants to break up with him. Janelle gets Mike to do it for her, but Nikki overhears Mike talking to Carter about it and thinks that Mike is going to break up with her. After Rags poops in his shoe, Stuart gives him to Heidi. Nikki breaks up with Mike. The next day, there is tension in the office. Carter tells Nikki the truth. She goes to Mike's apartment where Mike is hung over. As he goes back into his room to put on his pants, Heidi sits up in his bed...
When Mike says: ""Let's not get so dramatic, okay? This is not some cheesy soap opera."" he refers to Heather Locklear's long-time role as Amanda Woodward in the soap ""Melrose Place"".
James struggles to write an important speech to keep himself from being fired by Caitlin. Meanwhile, Paul is worried that Caitlin wants his office; she ends up moving into Mike's. And Nikki breaks up with Mike.
Caitlin implants secret background checks on all City Hall employees. Mike, Stuart and Carter break into her office to see the files. Caitlin goes to Nikki and Janelle's girls' night out. The mayor is offered a part in a movie filming in New York.
Mike tricks Nikki into seeing a couples counselor. The mayor takes an eighth grade test after being challenged by junior-high students. Stuart attempts to join Carter's gay gym to meet women.
Carter is named Activist of the Year. Stuart has a new paperweight that looks like a breast. Mike's continued jealousy of Caitlin causes him to make remarks to a gay magazine, which is misinterpreted, outing himself and the mayor. Paul is banned from the bathroom after insulting the new attendant.
The mayor considers quitting the senatorial race, teaming Mike and Caitlin to stop him. Carter becomes a kept man, and Paul and James scheme to play a good practical joke on Stuart.
Claudia's mother kicks Paul out of his house so he moves in with Stuart and Carter. Nikki dates the office's new young male intern. And Mike courts a wealthy socialite to donate money when the mayor's campaign runs out.
Mike and Caitlin agree to share the mayor on odd/even days. On Caitlin's day, Mike ""borrows"" the mayor to visit a kid who fell in a well. Unfortunately, they're 20 minutes late and the mayor falls in the now vacant well. Carter puts Rags in doggie day care. Paul appears on Who Wants to Be a Millionaire and wins $1,000,000. Stuart negotiates with firemen.
A newly rich Paul thinks Caitlin is hitting on him. The mayor wants a senator's endorsement and invites him, along with his staff, to Gracie Mansion for Thanksgiving. The senator thinks that Mike and Caitlin are a couple so they must share a room. Stuart and Deidre are back together.
Paul has invested in a politically themed restaurant. Mike struggles to run the city while the mayor is out of town. Deidre is stalking Caitlin a la ""Single White Female.""
Mike celebrates his five-year anniversary working for the mayor by taking Caitlin and going on a joyride with the mayor's '66 Mustang. Nikki and Carter accuse each other of being vain when City Hall ID photos are taken. The mayor wants to rekindle his romance with Janelle. Caitlin's busy schedule forces James back to speechwriting; he hires Deidre to be Mike's new secretary.
Mike invites Caitlin to his Christmas party as his only guest but his plans at romance are spoiled when she arrives with a date. Paul finds John McEnroe's headband in the City Hall clothing drive box. James finds a second job as a suicide hotline operator. Stuart installs a chin-up bar in the mayor's office, which the mayor promptly injures himself on.
The mayor struggles to find a date for a mayor's conference. Mike goes out with Caitlin's sister, making Caitlin jealous. Stuart tries to join Nikki, James and Janelle's art class to see nude women. Paul is upset that Carter makes more money than him.
Paul's cheap dentist puts braces on James instead of removing his infected tooth, causing problems in James' date with the new mail girl. The city's raffle to raise money for the Big Buddy program is screwed up when Paul skimps on the raffle tickets. Stuart and Carter blackmail Caitlin to decrease their workload.
After eating some of Rags' dog food, Paul develops a rash before he appears on ""The View."" Nikki helps him discover the wonders of makeup, though. Stuart tries to convince James that he's gay. Mike hires a hotshot director to film the mayor's Senate commercial, unaware that Trevor is Caitlin's ex-husband. After the commercial turns out to be a flop and Mike fires Trevor, Caitlin accuses him of being jealous. When a talk with Nikki persuades Mike to express his feelings for Caitlin, he sees her and Trevor in a heated embrace.
To quell a protest by senior citizens, Mike plans to get the city's first woman voter to vote for the mayor. When Mike finds out that Trevor isn't really British, he must decide whether to tell Caitlin or not. Carter protests anti-gay discrimination in an apartment building. James and Paul fight over a ""hey guy.""
While a reporter visits City Hall to do a story on Paul, the mayor thinks she's really there for him. Mike thinks Carter's boyfriend is hitting on him. The staff looks for good samaritans for a dinner. Stuart tries to convince James that he's getting fat.
Mike has a meeting with a tomato stand owner who refuses to move his stand so that the city can build a new performing arts center. He ultimately enlists James to compete against the man in a ""pig-off"" to decide whether the stand will stay or move. The mayor befriends a rapper who sampled one of his speeches in a song. Paul and Deirdre have memories of having sex at a concert 20 years before, driving Stuart jealous.
Mike helps the mayor deal with his feelings when his father unexpectedly dies. James thinks Caitlin has a crush on him. Paul's magic eight ball proves helpful to the staff.
With the President coming to visit City Hall, Mike is upset when Caitlin gets to meet him instead until plans change. The rest of the staff gathers at the bar, where Caitlin joins them. Nikki and Carter bet on who can pick up more women. Stuart tries to get Caitlin drunk; he succeeds and she leaves a drunken message for Mike. Paul tries to get James to help take his picture with the President.
The mayor prepares for a three-day trip across New York on his new campaign bus. Paul and James grow mustaches when they think that Carter's gets him the best assignments. Nikki becomes a female version of Stuart when she consults him for dating advice. After Mike discovers that Trevor has asked Caitlin to marry him again, he accidentally hits him with the bus. Mike and Caitlin kiss but their session is interrupted when Mike reveals he was deliberately aiming for Trevor.
While Michael and Caitlin fly to San Francisco, Stuart joins Carter for a protest and the mayor tries to have a light bulb changed.
Caitlin prepares to marry Trevor and elopes to Paris, where Mike follows and reveals that he loves her. James becomes angered with the mayor when he receives an undeserved war award. Stuart asks Nikki to pose for a ""charity"" swimsuit calendar.
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.
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.
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.
Charlie Crawford is late for his first press conference as the new deputy mayor. He later runs into trouble trying to settle a tollbooth workers strike when their lawyer is an ex-flame of his.
Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's attractive. Carter and Stuart deal with someone who keeps parking a bike in their parking space.
Caitlin causes a misunderstanding when she believes that Charlie is taking a Spanish class to improve relations with the Latin American community. Paul and the mayor struggle to create office water-cooler talk. Stuart becomes jealous of the time Carter has been spending with Caitlin.
Caitlin auditions for the job of co-host on ""Live with Regis."" Stuart and Paul work together supervising after bones are discovered under the Westside Highway. The mayor has an audio/visual link connected to the office while he is on vacation.
Caitlin goes out of her way to prove that she's fun after a blind man won't date her because she's not. Charlie accidentally talks Claudia into becoming a nun; she leaves Paul. The mayor researches religion.
Paul convinces his mother that he is dating Caitlin, so she won't be upset that Claudia left him. Charlie tries to prove to Caitlin that his girlfriend isn't dumb. A quickly made balloon for the Thanksgiving parade goes awry in New York.
Caitlin and Charlie fight the attention of Caitlin's new friend. Carter, Stuart and Paul compete for a trip to New Orleans with the mayor.
An overworked Charlie causes problems after beating the mayor at racquetball. Paul's annual request for a raise is approved by the mayor after his loss of self esteem. Stuart hires an actor to go out with Carter.
Mike has been in Zimbabwe for three weeks, so Paul teaches Caitlin about celibacy. Stuart convinces Angie that he's a biker guy. War on unemployment forces the mayor to work at a burger joint.
Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at a retirement community. The mayor's attempt to be more involved in the office process goes awry.
In an attempt to get over Claudia, Paul decides to move into a college dorm. Caitlin tries dating, after ending her relationship with Mike--but doesn't have much luck. The Mayor builds an access ramp after he gets caught parking in a handicapped parking space.
Caitlin sets the mayor up with her neighbor, Judith, who becomes way too much of an influence on the mayor. Carter helps Stuart prepare for a million dollar shot at a Rangers' game. Paul thinks he's Canadian.
Paul, Stuart and Carter rope reformed gambler Charlie into their poker night, and are responsible for his subsequent gambling bender. Caitlin tries to teach the mayor to be more self-sufficient.
When a supermodel sues the mayor, Charlie hires his old college friend to defend him. Charlie finds himself torn between two friends after Scott hits on Caitlin. Meanwhile, Paul and Stuart compete for the same woman.
Carter discovers an old love letter written by Stuart. He decides to set Stuart up with the addressee of the letter, a woman who turns out to be Stuart's ex-wife. The woman quickly manages to set a whipped Stuart into his old rut. Meanwhile, Caitlin hires an image consultant when the mayor's approval ratings go down. The consultant discovers that the mayor has a problem with women, causing Charlie to make himself over. And also, Paul worries that he's unrecognizable.
Julia's having a hard time dealing with her kiss with Charlie, so he asks her out. Their first date is a nightmare. Meanwhile, the mayor and his staff take the subway to prove that the mayor is in touch with the people. The train gets stuck in a tunnel, screwing up Charlie's plans for a second date. Meanwhile, Paul tells an exclusive cafe that Carter is Cuba Gooding Jr. to get reservations.
The mayor's daughter Meg returns and inspires Caitlin to be more spontaneous and free. Paul, Stuart and Carter give Charlie advice about compromising with Julia. This leads to Charlie deciding he's ready to commit, while Julia decides she's not.
Stuart is hired to write a porno movie. Charlie and Caitlin compete for a donation from a wealthy male chauvinist. After Paul poses as the Mayor's son for a golf tournament, he becomes confused when the Mayor actually begins paying attention to him.
Charlie tries out for a minor league baseball team, trying to relive his high school glory days. Caitlin encourages the pitcher to go easy on him. The mayor receives a death threat so he gets a bodyguard. After discovering that his job requires him to come into contact with the mayor so often, Paul receives a bodyguard also. Rags spends a day at the office.
Caitlin falls hard for a rich, young, sexy philanthropist. The Mayor is threatened when Charlie temporarily takes over as acting Mayor, and Paul becomes addicted to Carter's nicotine gum.
Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to work at City Hall and will go to any length to avoid people discovering their connection.
Charlie and Caitlin fight as she plans to go to the Caribbean for a week with Tim on the night of a police ride-along. On the ride-along, Charlie is shot...by Paul. Charlie fakes the severity of his injury to get Caitlin's attention. Charlie and Caitlin almost kiss, but Tim interrupts. Meanwhile, Carter and Stuart worry that they bicker like an old married couple and the Mayor hires an old prep school buddy who is now a bum.
Charlie and Caitlin double date with Tim and Charlie's crazy ex. However, Tim dumps Caitlin, who calls Charlie to come over. They kiss; he freaks out and just wants to be friends, but reconsiders and shows up on her doorstep later. The mayor remembers why he and Chad didn't get along in the first place.
Mike shows up at Caitlin's to announce that he's met someone. Meanwhile, the mayor is dating a judge who's not yet divorced. Charlie suggests that the mayor break it off, but after getting some advice from Mike, he decides to let the mayor do what makes him happy. Charlie impresses Caitlin but Mike interrupts again to announce his engagement.
The mayor has a tree cut down to impress his new girlfriend. Unfortunately, it was a tree planted by George Washington in 1796. Meanwhile, Charlie has a one-night stand, who turns out to be a rival mayoral candidate's campaign manager. Mike helps out with crisis control. Charlie and Caitlin decide to be friends for the time being, while Mike announces his return to City Hall.
Mike calls off his engagement with Allison and increases his presence in the office, making Charlie feel threatened. However, Charlie talks him into staying with Allison and marrying her--in City Hall. Meanwhile, Caitlin helps the mayor dress like a woman for a charity event.
The mayor's approval ratings are going down, thanks to his relationship with the not-yet-divorced Judge Simmons. Charlie convinces the mayor to seek quiet time with Claire at a friend's house--only he didn't anticipate the mayor showing up at his. Paul hires a publicist to improve his image. After going to a friend's baby shower, Caitlin becomes obsessed with having a baby. Carter lets her watch Rags for a day, but he swallows Charlie's pager. Caitlin decides not to have a child, but apparently, Carter does.
Carter's friend Michelle visits and begins dating Stuart. However, Carter has just asked her to be his child's surrogate mother. Meanwhile, Charlie and Caitlin struggle over what to do with incriminating photos of the mayor's opponent.
The mayor hires a political strategist to act as his campaign consultant. The consultant, Robin, is a bit of a psychic, predicting that a date of Charlie's will result in disaster, so Caitlin rushes to save him. As Stuart becomes more involved with Michelle, she tries to determine whether she is pregnant with Carter's artificially inseminated child yet. Stuart realizes that he may be the father after revealing that he forgot protection one night. However, Michelle discovers that she's not pregnant.
The mayor prepares to debate his opponent, while Charlie and Jennifer, his opponent's campaign manager have been dating for 3 weeks. The mayor wants Charlie to dump her, but he doesn't. When the mayor visits Charlie in the middle of the night to share something that may be damaging to his campaign, Jennifer may have overheard it. Meanwhile, Paul and Robin become involved; Paul thinks it's a relationship, while Robin thinks it's a fling.
Charlie discovers that Jennifer's ex is a woman. He becomes jealous when watching her be affectionate with Caitlin, something Caitlin dismisses until Jennifer kisses her on the lips. Claudia and Paul's divorce settlement may be affected by the mayor's bickering with Judge Claire.
Caitlin's mother Jane comes to visit when Caitlin tells her she finally has a boyfriend. In a panic, Caitlin enlists Charlie to play the part, and Charlie gets stuck having to attend a family wedding to help her. Meanwhile, Paul's childhood friend-turned-Victoria's Secret model, Rhea Durham, invites Paul and a guest backstage at the Victoria Secret Fashion Show. Stuart is the lucky attendee and is shocked to find out that Rhea has been in love with Paul all these years, but Paul is not interested. Also, on two hours sleep, the mayor must meet with the head of the teacher's union for her endorsement.
The Mayoral race hits a snag when Mayor Winston's opponent suffers a heart attack which forces him to drop out of the running, but his wife, Nancy Wheeler, steps in to take his place and surges in the polls due to an outpouring of sympathy. Meanwhile, Charlie gets punched in the face by Caitlin's new love interest and she makes him promise to be the bigger man by not fighting back.
Charlie endangers his relationship with Jennifer when he realizes that he loves his staff more than her. The Mayor decides to propose to Claire, but she says no because he's in the public eye and must be dishonest. This causes problems, because it's Election Day, and a truth-telling campaign by the Mayor could jeopardize his re-election.
Caitlin makes plans with the City Hall Santa without knowing what he looks like. Stuart wrestles with his feelings when he realizes that he's in love with Michelle. And Charlie must decide which staff member is most deserving of a nice new office.
Caitlin finds love with an older man, Tom -- whose daughter, Tracy, flirts with Charlie. Meanwhile the Mayor is depressed by the anniversary of his mother's death, but Carter introduces him to a woman, Christine, who cheers him up in more ways than one. Later, though, Carter reveals that Christine is the receiver of the Mayor's mother's donor heart, potentially threatening their relationship.
Caitlin surprises Charlie on his birthday by inviting his father, Ray, for a visit. What no one knows is that Ray is a con man who abandoned Charlie as a child, and who's about to con his way through City Hall as well. Meanwhile, Paul makes every effort to comfort Carter about Rags, who has passed into the great doggy beyond.
The Mayor's niece, Stephanie, pays a visit to City Hall and flirts with Charlie, who reciprocates - until he finds out who she is. Somewhat later he and Caitlin are caught in a compromising position in the Mayor's bedroom, trying to cover up for Stephanie's wild ways. Meanwhile, Mayor Winston and Carter get trapped in a car for hours, leading Carter to vow to give up his materialistic ways if they are saved, and Paul becomes a contestant on the popular dating show, ""Blind Date.""
When Carter is unexpectedly called to a late-night meeting, Charlie's left in charge of entertaining Spencer, a 16-year-old boy whom Carter sponsors through the ""Big Brother"" program. Having already had a date planned, Charlie has no choice but to bring Spencer along for the ride. Meanwhile, the Mayor is racked with guilt which is causing him insomnia.
Charlie has a hard time keeping up with Tracy, his new 23-year-old girlfriend who likes to party every night. Caitlin and Paul join them at a club one night and they are all arrested after one of Tracy's friends is caught with marijuana. Meanwhile, the Mayor is invited to a fund-raising gala by a very prominent member of the gay community, Martin, whom Carter has a crush on. Both Carter and Stuart also attend, and Martin hits on Stuart who is clueless to his advances, though they feed Carter's jealousy.
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.
Caitlin ends her relationship with Tom and tells Charlie she's interested in dating him. When they go out on their first date, things are awkward... until they end up in bed together, that is. But are they ready for a real relationship? Meanwhile, the Mayor hires a temp, Pete, to fill in for Stuart while he's out, but Paul and Carter see him as a threat.
Charlie and Caitlin struggle to find security in their new relationship. To spite Charlie for downplaying an encounter with an ex, Caitlin accompanies one of New York's ten sexiest men on a business date to make Charlie jealous. Meanwhile, the Mayor plots a way to one-up his rival, the Mayor of Los Angeles.
Charlie and Caitlin are caught having sex on a surveillance camera in the Mayor's office and their secret affair is blown. Carter is finally granted a foster child, but is frustrated when he sees that Paul is better with the baby than he is - until the Mayor helps him tap into his paternal instincts.
