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.

Toby leaves Dunder Mifflin, and Michael plans a huge goodbye party... out of joy. Angela refuses to help with it, so Michael turns to Phyllis. Dwight and Meredith harass Holly, their new HR representative.

A mysterious person in the office has made a huge mess in the microwave and will not clean it up. Meanwhile, Michael has to come to terms with the fact that there have been certain personnel changes in his staff without his knowing.

Michael decides to open a cafe-disco in his old office. Pam and Jim are planning a secret trip.