While everyone else in the office enjoys the spooky Halloween festivities and talks about the staff's costumes, Michael ponders who he should fire when the threat of downsizing becomes a reality and his boss orders him to fire one of his staff. Meanwhile, Jim and Pam put Dwight's resume on job-searching websites, which may make Michael's job a little easier, and Pam encourages Jim to set his goals higher by applying for a better job, which makes Jim consider his friendship with Pam.

The Dunder-Mifflin staffers join in kindergarten-like festivities for Valentine's Day while Michael heads to New York City for a conference with the corporate heads. After showing the documenters a tour of his favorite city, Michael accidentally lets slip to the others at the conference that he and Jan hooked up, and he finds himself in hot water when Jan and the new CFO of Dunder-Mifflin hear the story. Back in Scranton, Pam becomes irked when she discovers that Roy hasn't gotten her anything for Valentine's Day, Dwight struggles to find a gift for Angela, and Kelley talks off Jim's ear about her rather desperate affections for Ryan, who is less than interested.

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.