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.

Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to work at City Hall and will go to any length to avoid people discovering their connection.

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 Charlie gets stuck having to attend a family wedding to help her. Meanwhile, Paul's childhood friend-turned-Victoria's Secret model, Rhea Durham, invites Paul and a guest backstage at the Victoria Secret Fashion Show. Stuart is the lucky attendee and is shocked to find out that Rhea has been in love with Paul all these years, but Paul is not interested. Also, on two hours sleep, the mayor must meet with the head of the teacher's union for her endorsement.

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... until they end up in bed together, that is. But are they ready for a real relationship? Meanwhile, the Mayor hires a temp, Pete, to fill in for Stuart while he's out, but Paul and Carter see him as a threat.