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 break it off, but after getting some advice from Mike, he decides to let the mayor do what makes him happy. Charlie impresses Caitlin but Mike interrupts again to announce his engagement.

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 has a one-night stand, who turns out to be a rival mayoral candidate's campaign manager. Mike helps out with crisis control. Charlie and Caitlin decide to be friends for the time being, while Mike announces his return to City Hall.

Mike calls off his engagement with Allison and increases his presence in the office, making Charlie feel threatened. However, Charlie talks him into staying with Allison and marrying her--in City Hall. Meanwhile, Caitlin helps the mayor dress like a woman for a charity event.