The office staff play a basketball game against the warehouse workers in which Jim shows off to impress Pam and upstage her fiancee who is on the opposing team.

It's time for the "Dundies", Dunder Mifflin's annual awards banquet (held at the neighborhood Chili's), and the staff must endure the excruciating performance of their inept emcee, boss Michael Scott.

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.

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 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.

Michael had made it a point to have Movie Monday every week. He called the office into the conference room to watch a 30-minute installment of Varsity Blues, but Jan made an unexpected visit and did not like what she saw.

Michael decided to send his employees out into the field for sales calls. He paired himself up with Andy. He let the veterans choose who they wanted their partners to be. Phyllis chose Karen, Stanley chose Ryan and that left Jim and Dwight paired together. This wasn't the first time Dwight and Jim had done sales calls together.

Since Dwight's departure, Andy had been clinging to Michael. Andy's antics had been wearing very thin on his co-workers. In fact, Andy left Jim actually wishing Dwight would come back.

Michael comes to believe the office might be cursed in the wake of a freak accident. After scrutinizing each of his staffers' religious beliefs, he organizes a charity 5K "fun run."

Michael practices for the birth of Jan's baby by having Dwight go over possible birthing scenarios. Meanwhile, Michael tells Holly that he will pretend to dislike her for Jan's benefit.

Rumors spread that Dunder Mifflin is in financial trouble, so Michael tries to distract the office by having everyone play a murder mystery game called Belles, Bourbon, and Bullets. Meanwhile, Andy uses the game as a way to ask out Erin, but fears he may have asked out Erin's character, instead of Erin herself.

The staff grows increasingly uncomfortable with Michael and Holly's PDAs. Jim and Pam regret a champagne luncheon. Andy horns in on a romantic treasure hunt Gabe arranged for Erin.

Two new, young employees throw Dwight and Jim off balance; Andy returns from leadership training with a desire for revenge.