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 has a tree cut down to impress his new girlfriend. Unfortunately, it was a tree planted by George Washington in 1796. Meanwhile, Charlie...

Mike calls off his engagement with Allison and increases his presence in the office, making Charlie feel threatened. However, Charlie talks him into...

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...

Carter's friend Michelle visits and begins dating Stuart. However, Carter has just asked her to be his child's surrogate mother. Meanwhile, Charlie...

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...

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 discovers that Jennifer's ex is a woman. He becomes jealous when watching her be affectionate with Caitlin, something Caitlin dismisses...

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...

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...

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...

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...

Caitlin finds love with an older man, Tom -- whose daughter, Tracy, flirts with Charlie. Meanwhile the Mayor is depressed by the anniversary of his...

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...

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...

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...

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...

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...

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...

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......

Charlie and Caitlin struggle to find security in their new relationship. To spite Charlie for downplaying an encounter with an ex, Caitlin...

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...