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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.
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.
Dwight must confront his fear of public speaking when he is named Dunder-Mifflin’s Salesman of the Year. To prepare for a big convention where he is set to give a speech, Dwight turns to Michael to guide him in his quest to conquer the fear. Meanwhile, Pam gets wrapped up with wedding plans, but Jim has plans of a different sort: an escape route out of Dunder-Mifflin and Scranton, at least for long enough so that he doesn’t have to witness Pam’s wedding. While all of this is happening, the staffers battle it out over control of the thermostat.
A routine office day is changed when children come to Dunder Mifflin for “Take Your Daughter to Work Day.” Michael is surprised when he strikes up a friendship with the five-year old daughter of his sworn enemy, Toby. Pam is desperate to befriend her colleagues’ offspring and a misunderstanding puts Ryan under Stanley’s thumb
As Kevin and the rest of the crew worry about Kevin’s medical test results to see whether or not he has skin cancer, Michael gets angry because no one seems to have fun at the birthday party he threw for himself. Later, Michael takes everyone out to the skating rink to get their minds off of Kevin’s possible complications, and Pam and Jim go to the supermarket to pick up some presents for Kevin.
Dwight plays the role of Volunteer Sheriff after finding half a joint in the Dunder Mifflin parking lot leading to an investigation. Pam gives Jim a play challenge where he must be silent until he gives Pam a can of Coke.
When Michael takes over conflict resolution duties from HR, chaos ensues at Dunder Mifflin.
In the season finale, Dunder-Mifflin holds a Casino Night in the warehouse to benefit charity. While Michael faces the task of juggling two dates, Jim is forced to ponder the reality of transferring to the Stamford branch and what that means for his relationship with Pam.
While Michael and Dwight are out of the office for the day trying to close a deal on a new condo for Michael, Jim and Pam arrange for the staff to participate in an “Office Olympics,” where the workers play strange, invented games (among them, Dunderball, Hate Ball…and Pam Pong) that they usually play while the boss is out. At the end of the day, the festivities cheer up everyone – even the oblivious Michael.
The Office is forced into the parking lot for the day when a fire starts in the kitchen. To ease everyone’s boredom, Jim suggests a game of “Desert Island” and “Who Would You Do?,” where certain staff members reveal a little too much information about themselves. Throughout the day, Michael talks business with Ryan, leaving Dwight feeling left out.