Michael was in the holiday spirit and couldn't wait to share in it with his girlfriend, Carol. He had bought two tickets to paradise, hoping to whisk her away on a romantic vacation to Jamaica. Carol came by the office early to have a talk with Michael and it didn't go well.

Michael and Holly have sex for the first time, and Michael holds a fund-raiser for the office after it is burglarized. Dwight confides in Phyllis after Andy and Angela set a wedding date, and Jim runs into Pam's ex-fiancé Roy.

Andy pulls out all the stops to give Erin a memorable Secretary's Day. Michael reluctantly takes Erin out to lunch and lets slip about Andy's relationship with Angela. Meanwhile, Oscar circulates a video he created that compares Kevin's voice to Sesame Street's Cookie Monster.

Andy takes a break from flambéing cherries and composing rock operas to jumpstart his Dunder Mifflin comeback. When Robert drunkenly shuts down a nearby branch, Jim and Dwight join forces to outsmart a salesman from Scranton’s uglier sister city.

Pam interviews for a job in Philadelphia, but her potential manager reminds her of her former boss, Michael Scott. Dwight acquires the help of Angela in order to give his elderly Aunt Shirley a bath. Meanwhile, Andy attempts to make Pete and Erin feel uncomfortable.