Season 4

01 Catcher in the Bronx Episode 121st September 1999 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"". 02 James and the Giant Speech Episode 228th September 1999 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. 03 All the Mayor's Men Episode 35th October 1999 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. 04 These Shoes Were Made for Cheatin' Episode 412th October 1999 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. 05 Rebel Without a Chair Episode 519th October 1999 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. 06 The Mayor May Not Episode 62nd November 1999 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. 07 The Great Debate Episode 79th November 1999 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. 08 How to Bury a Millionaire Episode 816th November 1999 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. 09 The Thanksgiving Show Episode 923rd November 1999 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. 10 The Doorman Always Rings Twice Episode 1030th November 1999 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."" 11 Mustang Mikey Episode 117th December 1999 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. 12 My Dinner with Caitlin (a.k.a. Christmas 1999) Episode 1221st December 1999 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. 13 A Tale of Two Sisters Episode 1312th January 2000 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. 14 Casino Episode 142nd February 2000 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. 15 The Marry Caitlin Moore Show Episode 159th February 2000 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. 16 Suffragette City Episode 1616th February 2000 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."" 17 Mike's Best Friend's Boyfriend Episode 1723rd February 2000 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. 18 The Pig Whisperer Episode 188th March 2000 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. 19 Uneasy Rider Episode 1922nd March 2000 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. 20 About Last Night Episode 2019th April 2000 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. 21 Don't Get on the Bus Episode 2126th April 2000 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. 22 Airplane! Episode 223rd May 2000 While Michael and Caitlin fly to San Francisco, Stuart joins Carter for a protest and the mayor tries to have a light bulb changed. 23 An American Deputy Mayor in Paris Episode 2310th May 2000 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. 24 The Commitments Episode 2417th May 2000 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. 25 Goodbye (1) Episode 2524th May 2000 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. 26 Goodbye (2) Episode 2624th May 2000 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.