Mike shows up to announce his engagement and the mayor is dating a married judge.
The Mayor accidentally has an historical tree cut down, when trying to impress his girlfriend.
Mike returns to City Hall after cancelling his wedding plans, making Charlie feel threatened.
When the Mayor's approval rating is affected by his raltionship with a married woman, he uses Chalie's apartment as a "safe-house" for his affair.
When the Mayor's opponent plays dirty, Charlie and Caitlin obtain some incriminating photos and debate stooping to that level.
The Mayor hires a psychic consultant who predicts bad things for Charlies love life while Stewart thinks his girlfriend might be pregnant but isn't sure if it's his or Carters artificial insemination.
Charlie's relationship with the Mayor's opponent's campaign manager puts him in hot water when she may have overheard some damaging information about the Mayor.
When Charlie tells Caitlin that he thinks Jennifer is attracted to her, Caitlin thinks he is overreacting until Jennifer kisses her.
Charlie gets stuck going to a family wedding with Caitlin and her mother, when Caitlin tells everyone that he is the boyfriend.
When Mayor Winston's opponent Mr Wheeler suffers from a heart attack, his wife takes over in his place.
The Mayor tries to run a truthful campaign in order to get Clarie to marry him.
Caitlin makes a date with Santa Claus.
While grieving over the anniversary of his mother's death, the mayor is introduced to a woman who has an unusual connection with his mother.
Charlie's father is invited to his birthday by Caitlin, but she is unaware that he is a con man and that he has not seen Charlie since he was a child.
The Mayor niece comes to visit and stirs up trouble for everyone. Paul decides to go on the show "Blind Date."
Charlie is forced to take care of a 16 year old boy that Carter sponsers through a big brother program, when Carter is called in to work.
Caitlin and Ray join Charlie and his young girlfriend out at a club, which ends up landing them all in trouble when someone is caught with marijuana. The Mayor attends a fund-rasier hosted by a well known member of the gay community.
When Caitlin remembers Charlie from her past, she starts to reconsider her current relationship and her feelings for Charlie.
The Staff gets Palm phones from the Mayor, which accidentally allows Charlie to listen in on Caitlin's therapy sessions.
Caitlin and Charlie try dating, but when Charlie runs into an old flame it brings out a jealous streak in Caitlin.
The staff finds out about Charlie and Caitlin when they are caught on camera. The mayor helps Carter find his paternal instincts when he is granted a foster child.