Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's attractive. Carter and Stuart deal with someone who keeps parking a bike in their parking space.

Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at a retirement community. The mayor's attempt to be more involved in the office process goes awry.

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 through the ""Big Brother"" program. Having already had a date planned, Charlie has no choice but to bring Spencer along for the ride. Meanwhile, the Mayor is racked with guilt which is causing him insomnia.