Season 5
(2000)
Cast
as Charlie Crawford
as Caitlin Moore
as Paul Lassiter
as Stuart Bondek
as Carter Heywood
as Randall Winston
Episodes
Hello Charlie 7.0
October 18, 2000
Charlie Crawford is late for his first press conference as the new deputy mayor. He later runs into trouble trying to s…
Smile 7.0
October 25, 2000
Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only be…
The Spanish Prisoner 7.0
November 1, 2000
Caitlin causes a misunderstanding when she believes that Charlie is taking a Spanish class to improve relations with th…
The Bone Collectors 7.0
November 8, 2000
Caitlin auditions for the job of co-host on ""Live with Regis."" Stuart and Paul work together supervising after bones …
Blind Faith 7.0
November 15, 2000
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 acciden…
Balloons over Broadway 7.0
November 22, 2000
Paul convinces his mother that he is dating Caitlin, so she won't be upset that Claudia left him. Charlie tries to prov…
Lost and Found 1.0
November 29, 2000
Caitlin and Charlie fight the attention of Caitlin's new friend. Carter, Stuart and Paul compete for a trip to New Orle…
All the Wrong Moves 7.0
December 6, 2000
An overworked Charlie causes problems after beating the mayor at racquetball. Paul's annual request for a raise is appr…
The Burgers of Wrath 7.0
December 13, 2000
Mike has been in Zimbabwe for three weeks, so Paul teaches Caitlin about celibacy. Stuart convinces Angie that he's a b…
Toy Story 7.0
December 20, 2000
Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at …
The Perfect Dorm 7.0
January 10, 2001
In an attempt to get over Claudia, Paul decides to move into a college dorm. Caitlin tries dating, after ending her re…
Hey Judith 7.0
January 17, 2001
Caitlin sets the mayor up with her neighbor, Judith, who becomes way too much of an influence on the mayor. Carter help…
The Gambler 7.0
January 24, 2001
Paul, Stuart and Carter rope reformed gambler Charlie into their poker night, and are responsible for his subsequent ga…
In the Company of Dudes 7.0
February 7, 2001
When a supermodel sues the mayor, Charlie hires his old college friend to defend him. Charlie finds himself torn betwee…
The Image Maker 7.0
February 14, 2001
Carter discovers an old love letter written by Stuart. He decides to set Stuart up with the addressee of the letter, a …
Trainstopping 7.0
February 21, 2001
Julia's having a hard time dealing with her kiss with Charlie, so he asks her out. Their first date is a nightmare. Mea…
Rain on My Charades 7.0
February 28, 2001
The mayor's daughter Meg returns and inspires Caitlin to be more spontaneous and free. Paul, Stuart and Carter give Cha…
You've Got Male 8.0
April 25, 2001
Stuart is hired to write a porno movie. Charlie and Caitlin compete for a donation from a wealthy male chauvinist. Af…
Minor League 8.0
May 2, 2001
Charlie tries out for a minor league baseball team, trying to relive his high school glory days. Caitlin encourages th…
Science Friction 8.0
May 9, 2001
Caitlin falls hard for a rich, young, sexy philanthropist. The Mayor is threatened when Charlie temporarily takes over …
Brotherly Love 8.0
May 16, 2001
Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to wo…
A Shot in the Dark (1) 8.0
May 23, 2001
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. …
A Shot in the Dark (2) 8.0
May 23, 2001
Charlie and Caitlin double date with Tim and Charlie's crazy ex. However, Tim dumps Caitlin, who calls Charlie to come…