Michael invites Jim and Pam and Andy and Angela to a couples-only dinner party, which makes Dwight very jealous. However, the only thing he's missing is a ringside seat to witness Michael and Jan's extremely dysfunctional home life.
Kevin and Andy team up to reclaim the stolen Dunder Mifflin parking spaces, which forces them into a showdown with the other four bosses of the office park. Meanwhile, Michael becomes fascinated by a woman modeling chairs in a catalog.
Michael and Dwight go to New York to party with Ryan, who is having lots of personal and professional problems. The rest of the office employees work late, and wind up getting locked in the business park.
Dunder-Mifflin participates in a high school job fair, but few students are interested. Jim, Andy, and Kevin play a round of golf with a prospective client. Back at the office, everyone but Dwight and Angela leave for the day.
Michael throws an extravagant going-away party for Toby, and falls in love with the woman who is replacing him. Jim plans to propose to Pam at the party, but gets out-staged. Back at corporate, Ryan is arrested for fraud.
Michael tries to motivate the Scranton branch to lose weight as part of an interoffice competition. Jim is lost after Pam leaves for art school in New York, and Angela continues to see Dwight even though she is now engaged to Andy.
A confession at an H.R. business ethics seminar leads to a dispute between Michael and Holly over whether Meredith should be fired. Dwight tries to prove to Jim how long he can go without taking a personal break
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.
Holly is transferred back to New Hampshire after corporate discovers that she and Michael are dating. Dwight tries to apply to Cornell to get under Andy's skin. Jim's brothers and Pam decide to play a trick on Jim when they meet for lunch.
When Michael discovers that corporate has brought back Toby to replace Holly, he tries to frame him with drugs to get him fired. Meanwhile, Jim surprises Pam by buying his parents' house, and Pam files a secret complaint about the microwave.
Michael has to spend the office surplus by they end of the day, but he can't decide between a copier or new chairs. Dwight plays a dirty trick on Angela as they prepare for Andy and Angela's wedding on the beet farm.
Phyllis blackmails Angela into doing the work for the Christmas party, which Michael turns into an intervention after Meredith gets drunk and sets her hair on fire. Meanwhile, Dwight corners the market on a popular Christmas gift.