Pam meets Jim's brothers, who pull a prank on Jim, which embarrasses her. Their plans to continue dating are dashed and they break up, and Darryl teaches Michael to sing the blues. When corporate transfers Holly to Nashua, Michael (with Darryl's help) moves her back to New Hampshire. Pam gets a part-time job at corporate to pay for art school, and Jim is further unsettled after Roy insinuates that he is losing her. On Phyllis's advice, Dwight gives Angela an ultimatum to break up with Andy, which she refuses to do. Michael holds an auction to raise money for all the items lost. Michael and Holly date, have sex in the office and inadvertently lead to the office being robbed. The separation between Jim and Pam starts to take a toll on their relationship. Michael goes to Holly for comfort and they agree to date. Meanwhile, Michael pretends to dislike Holly for Jan's benefit, but Jan senses their connection and asks Michael not to date Holly. When Jan arrives for the office baby shower, she has already had baby Astrid, excluding Michael from the process, and he feels disconnected from the baby. Michael practices for the birth of Jan's baby by having Dwight go over possible birthing scenarios. Meanwhile, Jim makes Dwight comply with the company's "time theft" policy by timing every second of his personal activity. Holly is ostracized by the staff, but when she is humiliated by the head of Human Resources, Michael once again supports her. Michael lets everyone speak freely about their unethical behavior at work and Meredith, in particular, causes a rift between Michael and Holly when Meredith admits a supplier gives her discounts on products and steak coupons in exchange for sex. A disgraced Ryan returns to the Scranton office as a temp.įollowing Ryan's recent scandal, Holly holds an ethics seminar. Jim misses Pam who attends art school in New York, and he finally proposes. Andy plans his wedding to Angela, while she continues her affair with Dwight. Michael pursues a friendship with his new HR rep, Holly.
Over eight weeks of the summer, a Dunder Mifflin weight-loss initiative causes the branch to diet and become obsessed with their weight. The season ends with Pam learning she is pregnant. The company becomes successful and eventually, Dunder Mifflin is forced to buy them out. Michael eventually cannot deal with his dictator-like changes and quits to form his own company taking Pam and Ryan with him. Eventually, new boss Charles Miner enters later in the season and causes trouble for Michael. Meanwhile Jim and Pam become engaged and struggle through the difficulties of a long-distance relationship while Pam is studying art in New York. The start of the season revolves around Michael attempting to woo Holly and eventually succeeds only for David Wallace to transfer her to another branch forcing the two to end their relationship just when it got started. The previous season was Season 4 and the next season was Season 6. It ended on May 14, 2009, and consisted of 28 episodes, making it the longest season of the series. Season 5 of The Office began on September 25, 2008, on NBC.
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