Michael could not be happier when Toby has to take a leave of absence and corporate sends Holly Flax to cover for him. Pam is forced to do a second Christmas party after Michael wants the party to be on the day Holly returns to Scranton. Meanwhile, Jim regrets agreeing to a snowball fight with Dwight.
Event Year: 2005
Training Day
The new manager, Deangelo Vickers, has everyone hoping to make good first impressions: Andy finds himself awkwardly typecast while Jim and Pam worry that they've come on too strong. Only Dwight is apathetic about the new leader.
Welcome Party
Robert California forces the office to throw a welcome party for Nellie, but the Party Planning Committee works on ways to sabotage it. Meanwhile, Erin tries to help Andy figure out a way to break up with Jessica.
Free Family Portrait Studio
Dwight offers free family portraits, and a stolen diaper leads to a high-speed car chase. With help from David Wallace, Andy goes undercover to try to get his job back. A new business opportunity arises for Robert California.
A.A.R.M.
Jim convinces Dwight that he needs to choose someone to act as an Assistant to the Assistant Regional Manager; the two subsequently hold tryouts for the position. After her daycare turns away her child, Angela is forced to bring her kid to work. Andy auditions for “The Next Great A Cappella Sensation”.
Booze Cruise
Michael takes the entire Dunder-Mifflin staff on a motivational cruise aboard a party boat on Lake Wallenpaupack, but his planned presentation is bogged down by numerous distractions, including a dance contest, limbo, snorkel shots, and the pushy Captain Jack. Also, Jim and Katy’s relationship hits the rocks as Roy and Pam finally set a wedding date, which does more than disappoint Jim, and by the end of the night, Michael’s motivational cruise doesn’t go completely to waste when he shares a heart-to-heart with one of the workers.
Valentine's Day
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.
The Negotiation
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.
Beach Games
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.
Employee Transfer
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.