While Michael and Dwight are out of the office for the day trying to close a deal on a new condo for Michael, Jim and Pam arrange for the staff to participate in an "Office Olympics," where the workers play strange, invented games (among them, Dunderball, Hate Ball...and Pam Pong) that they usually play while the boss is out. At the end of the day, the festivities cheer up everyone - even the oblivious Michael.

As Kevin and the rest of the crew worry about Kevin's medical test results to see whether or not he has skin cancer, Michael gets angry because no one seems to have fun at the birthday party he threw for himself. Later, Michael takes everyone out to the skating rink to get their minds off of Kevin's possible complications, and Pam and Jim go to the supermarket to pick up some presents for Kevin.

In the season finale, Dunder-Mifflin holds a Casino Night in the warehouse to benefit charity. While Michael faces the task of juggling two dates, Jim is forced to ponder the reality of transferring to the Stamford branch and what that means for his relationship with Pam.

Michael was educating the entire staff about Diwali, the Hindu holiday that Kelly celebrated. Kelly had invited everybody from work to the celebration. Pam was unsure if she was going to make it, she later confided in Angela that she was saddened because she had nobody to attend the celebration with.

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, believing he has herpes, contacts all his ex-girlfriends, including Jan and Holly. Andy tries to play on Erin’s compassionate side by holding a sex education meeting for the office.

One year later, Dunder Mifflin employees past and present reunite for a panel discussion about the documentary and to attend Dwight and Angela's wedding.