Michael gets upset when Holly returns from the holidays without an engagement ring, but still together with her boyfriend. Meanwhile, Pam tries to help her co-workers keep with their New Year's resolutions.
When Jim gets an emergency phone call from Helene, he is forced to leave Michael in the bathroom of a gas station. Meanwhile, Holly, Erin and Dwight set out on a journey to find Michael. Back at the office Pam's artwork starts a captioning contest that seems to offend Gabe.
It's Valentine's Day, and the office is fed up with Michael and Holly's PDA, Andy helps Erin solve Gabe's riddles to find her gift, and Jim and Pam get drunk and try to find a place in the office to have sex.
As the office gets ready for Michael's final day at Dunder Mifflin, Michael doesn't tell anyone that he's leaving a day early. Meanwhile, Deangelo accompanies a nervous Andy on a visit to one of Michael's old clients.
The Scranton branch puts together a search committee to find the next boss, but the pool of interviewees proves to be less than impressive, and Dwight demands an interview in spite of his gun accident.
New Dunder Mifflin CEO Robert California leaves a piece of paper with a line down the middle that has names of the Scranton staff on either side of it, leading everyone to try and figure out what it means.
After the entire warehouse staff wins the lottery and quits their job, Darryl becomes depressed and demands to be fired. Meanwhile, the office staff is forced to load the truck for their orders themselves.
Erin is worried that she is about to get fired after she organizes a disastrous office Halloween party for Robert and his son. Meanwhile, Robert probes the minds of the employees to come up with the perfect spooky story.
Andy decides to motivate and inspire everyone by taking them on a field trip to Gettysburg. Some people in the office stay behind and Robert California asks them to come up with Dunder Mifflin/Sabre's next big idea.
Robert brings his wife to the office so that she can find a job, but he gives Andy conflicting messages about whether to hire her. Meanwhile, Dwight opens a gym in the building and tries to persuade Darryl to join.