September 25, 2001 • 22m
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. Cha...Read more
September 25, 2001 • 22m
The mayor has a tree cut down to impress his new girlfriend. Unfortunately, it was a tree planted by George Washington in 1796. ...Read more
October 2, 2001 • 22m
Mike calls off his engagement with Allison and increases his presence in the office, making Charlie feel threatened. However, Cha...Read more
October 9, 2001 • 22m
The mayor's approval ratings are going down, thanks to his relationship with the not-yet-divorced Judge Simmons. Charlie convince...Read more
October 16, 2001 • 22m
Carter's friend Michelle visits and begins dating Stuart. However, Carter has just asked her to be his child's surrogate mother. ...Read more
October 23, 2001 • 22m
The mayor hires a political strategist to act as his campaign consultant. The consultant, Robin, is a bit of a psychic, predictin...Read more
November 6, 2001 • 22m
The mayor prepares to debate his opponent, while Charlie and Jennifer, his opponent's campaign manager have been dating for 3 week...Read more
November 6, 2001 • 22m
Charlie discovers that Jennifer's ex is a woman. He becomes jealous when watching her be affectionate with Caitlin, something Cai...Read more
November 13, 2001 • 22m
Caitlin's mother Jane comes to visit when Caitlin tells her she finally has a boyfriend. In a panic, Caitlin enlists Charlie to pl...Read more
November 20, 2001 • 22m
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...Read more
November 27, 2001 • 22m
Charlie endangers his relationship with Jennifer when he realizes that he loves his staff more than her. The Mayor decides to pro...Read more
December 11, 2001 • 22m
Caitlin makes plans with the City Hall Santa without knowing what he looks like. Stuart wrestles with his feelings when he realiz...Read more
January 8, 2002 • 22m
Caitlin finds love with an older man, Tom -- whose daughter, Tracy, flirts with Charlie. Meanwhile the Mayor is depressed by the ...Read more
March 5, 2002 • 22m
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...Read more
March 12, 2002 • 22m
The Mayor's niece, Stephanie, pays a visit to City Hall and flirts with Charlie, who reciprocates - until he finds out who she is....Read more
March 19, 2002 • 22m
When Carter is unexpectedly called to a late-night meeting, Charlie's left in charge of entertaining Spencer, a 16-year-old boy wh...Read more
March 26, 2002 • 22m
Charlie has a hard time keeping up with Tracy, his new 23-year-old girlfriend who likes to party every night. Caitlin and Paul joi...Read more
April 9, 2002 • 22m
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 w...Read more
April 16, 2002 • 22m
Caitlin is confused by the kiss she and Charlie shared and seeks the advice of a therapist. Meanwhile, the Mayor buys the staff pa...Read more
April 23, 2002 • 22m
Caitlin ends her relationship with Tom and tells Charlie she's interested in dating him. When they go out on their first date, thi...Read more
April 30, 2002 • 22m
Charlie and Caitlin struggle to find security in their new relationship. To spite Charlie for downplaying an encounter with an ex,...Read more
April 30, 2002 • 22m
Charlie and Caitlin are caught having sex on a surveillance camera in the Mayor's office and their secret affair is blown. Carter ...Read more