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 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.
Jan holds a “Women in the Workplace” seminar at Dunder-Mifflin for the paper company’s female employees. Michael, feeling more than a bit left out, decides to have his own “seminar” when he takes the male workers down to the warehouse.
Michael hosts a Christmas party at the office, but somehow manages to decrease the holiday cheer when he changes the arranged secret Santa pairs to a game of “Yankee Swap,” where everyone gives their pre-bought presents to a different, random worker. To boost morale, Michael introduces vodka shots while the others compete for an iPod, Jim hopes that his sentimental present, meant for Pam, doesn’t end up with Dwight, and Angela becomes enraged about Michael’s party changes.
When someone soils the carpet in Michael’s office, Michael sees it as a form of hatred towards him and realizes for the first time that not everyone may like him. Due to the odor of his office, Michael temporarily switches workspaces with Jim, and while there, Michael reminisces of his pre-management days, reliving pranks with Dwight that he and Todd Packer played on the staff. Meanwhile, Jim realizes why Kelly sits alone in the back of the office as he plays messenger for a childish flirtation between Kelly and Ryan, and Pam tries to cope with the day without Jim to make her laugh.
Michael starts monitoring the emails sent out in the Dunder-Mifflin workplace, upsetting the employees. Meanwhile, Pam believes that the relationship between Dwight and Angela is more than just worker to worker, Jim throws an office BBQ at his house in order to show his roommate the kinds of people he deals with everyday, and Michael, after annoying everyone at his improv classes, crashes Jim’s party with a terrible karaoke number.
When Michael slips some sly references about Pam in his conversations with Jim, Jim quickly tries to do damage control to make sure that no one else in the office finds about his crush on Pam, all while slamming himself with regret for ever telling Michael in the first place. Jim goes to drastic measures, even bonding with Michael at a Hooters restaurant for lunch. Nonetheless, Jim’s efforts do little to keep Michael from revealing the secret, but Jim smooths the situation over with Pam to make it seem like nothing more than a tiny crush in the past. Meanwhile, Dwight conducts an investigation about Oscar’s mysterious absence from work, and what Dwight finds, though it goes way over his head, is surprising.
Michael meets with all of his underlings to discuss their performance in the office so far. However, Michael focuses more on getting feedback about his relationship with Jan than whether or not the workers are doing their job. Later, a nervous Michael plans to shuffle through the employee suggestion box to steal exciting ideas for his imminent discussion with Jan about his own performance, but that falls apart when Jan asks to sit in on the discussion. Meanwhile, Jim and Pam try to keep Dwight under the wrong impression that the day is Friday instead of Thursday.
When Michael and Jan try to nail down a potential new client, Christian, by taking him out to Chili’s, Michael surprises everyone with what – or who – he does. Meanwhile, back at the office, Jim finds a semi-autobiographical script that Michael has written called Threat Level: Midnight, and he, Pam, Kevin, and the rest of the Dunder-Mifflin workers have a great time acting it out. Later that night, Pam and Jim share their first unofficial date, complete with dinner (a sandwich), candlelight, and Dwight’s pathetic fireworks display.
Axe deals with a major family disturbance involving Lara and the kids. Chuck considers the potential pitfalls of his personal life while being vetted for political advancement. Wendy tries to right a wrong she committed against Axe. At an impromptu dinner Chuck and Wendy open up to each other.
