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.
Michael and Darryl head to Dunder Mifflen headquarters to lobby for a pay increase. Meanwhile, Jim must deal with the consequences of Pam's confession to Roy.
Michael is being considered for a position in corporate, but also plans a day of "Survivor" like competitions while the office workers visit Lake Scranton. Pam is not asked to join in on any of the competitions and is forced to sit and watch Jim and Karen have fun.
Pam is embarrassed when she is the only person at corporate wearing a costume on Halloween. Holly and Michael take the long trip to Nashua after they get some shocking news from corporate. Meanwhile, Dwight torments Andy and tries to get under his skin.
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.
Jim and Pam return from their honeymoon and learn, to their horror, that Michael is dating Pam’s mom. Meanwhile, Dwight gives Jim a “gift”–which actually has a listening device attached to it.
When a competing sales associate steals a Dunder Mifflin client, Michael, Jim and Dwight decide to set up a sting to find out his sales secrets. Andy decides to start a band after finding out a friend from college has a successful music career.
After reading an article about China growing as a global power, Michael decides China must be stopped before they take over the US. Everyone in the office complains about Dwight's building standards and Pam threatens to move Dunder Mifflin to a new building.
The office holds a garage sale in the warehouse. Michael decides to propose to Holly, and runs into trouble thinking of how to do it well.
Andy makes a game-changing decision and takes a road-trip odyssey in the name of romance. Elsewhere, Nellie arrives at the Scranton branch and sets out to seize the manager position.