October 18, 2000 • 22m
Charlie Crawford is late for his first press conference as the new deputy mayor. He later runs into trouble trying to settle a tol...Read more
October 25, 2000 • 22m
Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's ...Read more
November 1, 2000 • 22m
Caitlin causes a misunderstanding when she believes that Charlie is taking a Spanish class to improve relations with the Latin Ame...Read more
November 8, 2000 • 22m
Caitlin auditions for the job of co-host on ""Live with Regis."" Stuart and Paul work together supervising after bones are discove...Read more
November 15, 2000 • 22m
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...Read more
November 22, 2000 • 22m
Paul convinces his mother that he is dating Caitlin, so she won't be upset that Claudia left him. Charlie tries to prove to Caitli...Read more
November 29, 2000 • 22m
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.
December 6, 2000 • 22m
An overworked Charlie causes problems after beating the mayor at racquetball. Paul's annual request for a raise is approved by the...Read more
December 13, 2000 • 22m
Mike has been in Zimbabwe for three weeks, so Paul teaches Caitlin about celibacy. Stuart convinces Angie that he's a biker guy. W...Read more
December 20, 2000 • 22m
Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at a retiremen...Read more
January 10, 2001 • 22m
In an attempt to get over Claudia, Paul decides to move into a college dorm. Caitlin tries dating, after ending her relationship ...Read more
January 17, 2001 • 22m
Caitlin sets the mayor up with her neighbor, Judith, who becomes way too much of an influence on the mayor. Carter helps Stuart pr...Read more
January 24, 2001 • 22m
Paul, Stuart and Carter rope reformed gambler Charlie into their poker night, and are responsible for his subsequent gambling bend...Read more
February 7, 2001 • 22m
When a supermodel sues the mayor, Charlie hires his old college friend to defend him. Charlie finds himself torn between two frien...Read more
February 14, 2001 • 22m
Carter discovers an old love letter written by Stuart. He decides to set Stuart up with the addressee of the letter, a woman who t...Read more
February 21, 2001 • 22m
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...Read more
February 28, 2001 • 22m
The mayor's daughter Meg returns and inspires Caitlin to be more spontaneous and free. Paul, Stuart and Carter give Charlie advice...Read more
April 25, 2001 • 22m
Stuart is hired to write a porno movie. Charlie and Caitlin compete for a donation from a wealthy male chauvinist. After Paul po...Read more
May 2, 2001 • 22m
Charlie tries out for a minor league baseball team, trying to relive his high school glory days. Caitlin encourages the pitcher t...Read more
May 9, 2001 • 22m
Caitlin falls hard for a rich, young, sexy philanthropist. The Mayor is threatened when Charlie temporarily takes over as acting M...Read more
May 16, 2001 • 22m
Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to work at City ...Read more
May 23, 2001 • 22m
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 rid...Read more
May 23, 2001 • 22m
Charlie and Caitlin double date with Tim and Charlie's crazy ex. However, Tim dumps Caitlin, who calls Charlie to come over. The...Read more