The Office - Season 5 (2008)

Michael and Holly have sex for the first time, and Michael holds a fundraiser for the office after it is burglarized. Dwight confides in Phyllis after Andy and Angela set a wedding date, and Jim runs into Pam's ex-fiancé, Roy.

Holly is transferred back to New Hampshire after corporate discovers that she and Michael are dating. Dwight tries to apply to Cornell to get under Andy's skin. Jim's brothers and Pam decide to play a trick on Jim when they meet for lunch.

Dwight and Jim believe that something is suspicious about their low customer performance ratings. After consulting with Angela, Andy finds the perfect site for their wedding--Dwight's beet farm.

David Wallace sends Michael on a business trip to Winnipeg to help him forget about Holly's transfer to Nashua, and Pam tells Jim that she failed a class and has to stay in New York City.

When Michael discovers that corporate has brought back Toby to replace Holly, he tries to frame him with drugs and to get him fired. Meanwhile, Pam has issues with the disgusting microwave. Finally, Jim surprises Pam by buying his parents' house.

Michael has to spend the office surplus by they end of the day, but he can't decide between a copier or new chairs. Dwight plays a dirty trick on Angela as they prepare for Andy and Angela's wedding on the beet farm.

Phyllis blackmails Angela into doing the work for the Christmas party, which Michael turns into an intervention after Meredith gets drunk and sets her hair on fire. Meanwhile, Dwight corners the market on a popular Christmas gift.

Moments before he leaves for New York for a meeting with David Wallace, Michael tells Andy that Angela and Dwight are seeing each other. Andy and Dwight then decide to have it out in the parking lot.

Michael's conscience gets the best of him after he and Dwight go undercover to scout a family-run competitor. Back at the office, everyone else spends the day debating whether Hilary Swank is hot.

Dwight's too-realistic fire alarm gives Stanley a heart attack. When he returns, Michael learns that he is the cause of Stanley's stress. To remedy the situation, he forces the office to throw a roast for him.

While on lecture tour to other Dunder Mifflin branches, Michael and Pam discover that Jim's ex-girlfriend Karen is pregnant. At the office, Andy falls for a prospective client, and Jim and Dwight try to set up Kelly's birthday party.

Michael and Pam go to Nashua and discover that Holly has a new boyfriend. At the office, Jim and Dwight try to come up with a theme for Kelly's birthday party, and Angela gets a new cat.

Michael holds a lonely hearts party on Valentine's Day at the office, hoping that he will run into a woman he met earlier that day at a blood drive. Meanwhile, Jim and Pam have an awkward lunch with Phillis and Bob Vance.

Michael asks Dwight to be the scapegoat for one of his business ideas that backfired badly on him. But when that idea has an unexpected positive upside, Dwight still takes credit and Michael becomes furious.

Michael gets upset when he gets a new boss to act as a buffer between him and David Wallace, and he gets even more upset when he disbands the Party Planning Committee and cancels Michael's fifteenth anniversary party.

As Michael prepares to leave Dunder Mifflin, he announces that he will form his own paper company. Will anybody join him?

Michael and Pam begin their first day as the Michael Scott Paper Company putting together the rest of the staff and trying to raise money.

Tension and disillusionment begin to emerge as Michael, Pam, and Ryan move the Michael Scott Paper Company into a cramped "workspace" at the business park.

Dwight chooses loyalty to Dunder Mifflin over loyalty to Michael, which leads to a bitter battle between Michael and Dwight over Dwight's accounts. Back at Dunder Mifflin, Jim pretends to confide in Andy.

The Michael Scott Paper Company is gaining clients by offering lower prices than Dunder Mifflin, but is going broke in the process. However, Dunder Mifflin is losing clients to Michael, and is desperate to buy him out.

Michael returns to Dunder Mifflin and brings Ryan and Pam in as salespeople, but the existing salespeople demand that Michael return the clients they stole back to them. Meanwhile, some employees take the idea of Casual Friday too far.

Michael tries to create a place to escape from work in the storage room that used to house the Michael Scott Paper Company, while Jim and Pam consider taking off and getting married that day.

Michael runs into Holly at the company picnic, and the two of them accidentally reveal that the Buffalo branch is closing during a comedy skit before corporate has made the announcement.