The fifth season of The Office begins with Pam at art school in New York, Ryan returning to Dunder-Mifflin, Dwight and Angela having an affair behind Andy’s back, and Michael meeting the apparent woman of his dreams in new human-resources head Holly. Pam eventually comes back from art school, gets engaged to Jim and gets pregnant, while Holly and Michael enjoy a short but intense relationship before she’s transferred out of town. Angela breaks up with both Andy and Dwight, and all three end up alone. After being disrespected by a new vice president, Michael quits Dunder-Mifflin to start his own company, but returns triumphantly when he gets bought out and his rival is banished from Scranton. Read all about it in The Office Season 5 episode guide.
Title: “Weight Loss”
Original Airdate: September 25, 2008
Over the course of eight weeks during the summer, the Dunder-Mifflin employees participate in a company-wide weight-loss challenge, which inspires Kelly to anorexia and Dwight to new levels of obnoxiousness. Meanwhile, Pam heads off to art school in New York, and the separation inspires Jim to propose to her at a rest stop (she says yes). Michael and Holly continue flirting even as she goes on a few dates with a yoga instructor, and Dwight and Angela continue their illicit affair while Andy obliviously plans his and Angela’s wedding up to her impossible standards. Ryan returns to Dunder-Mifflin as a temp, filling in for Pam at reception, and Michael appears to be the only person happy to see him.
Title: “Business Ethics”
Original Airdate: October 9, 2008
Thanks to Ryan’s scandal at corporate, Holly has to conduct a business-ethics seminar for the office. Michael encourages everyone to confess their ethical transgressions, which leads to Meredith admitting that she regularly sleeps with a vendor to get a discount on supplies and free Outback Steakhouse coupons. Holly decides that Meredith needs to be terminated for this infraction, and she and Michael have a tense lunch over which he tries to convince her otherwise. Eventually, HR at corporate orders the affair swept under the rug. Meanwhile, Jim and Pam announce their engagement to their co-workers, who respond with general indifference.
Title: “Baby Shower”
Original Airdate: October 16, 2008
Michael plans a baby shower for Jan despite the fact that he’s not the father of her baby. She shows up already having given birth, toting along her newborn daughter Astrid. The rather pathetic shower goes ahead anyway, with Michael treating Holly meanly so as not to upset Jan. Michael feels no connection to baby Astrid when he holds her, but when Jan tells him not to date Holly, he goes back to the office and holds Holly instead; they definitely have a connection, and she agrees to go out with him. Jim and Pam spend the day having trouble connecting with each other over the phone.
Title: “Crime Aid”
Original Airdate: October 23, 2008
Michael and Holly leave the office door unlocked following an after-hours tryst, and Dunder-Mifflin is robbed. To make up for the losses, Michael stages a charity auction with some seriously lame items, including a pair of Bruce Springsteen tickets that don’t actually exist. Dwight freaks out about Angela and Andy setting a date for their wedding, and follows Phyllis’ advice to give Angela an ultimatum, but Angela doesn’t respond. Jim gets paranoid about what Pam might be doing in New York without him, but stops short of driving out there to check on her.
Title: “Employee Transfer”
Original Airdate: October 30, 2008
After corporate discovers that Holly and Michael are dating, they transfer Holly back to New Hampshire. On the drive from Scranton, she decides that a long-distance relationship with Michael wouldn’t work, and even though he pleads with her to reconsider, they break up. To mess with Andy, Dwight decides to become a huge Cornell devotee, stocking up on the school’s memorabilia and even sending in an application. Jim and Pam have lunch in New York with Jim’s brothers, who play a bizarre “prank” that involves belittling Pam’s aspirations of becoming an artist, but she ingratiates herself to them by playing along with this rather cruel ruse.
Title: “Customer Survey”
Original Airdate: November 6, 2008
The annual customer-service surveys come in, and Jim and Dwight both have negative reports. It turns out that Kelly doctored the results to get back at them for not coming to her America’s Got Talent finale party. Michael finds out, but instead of reprimanding Kelly he commiserates with her over the difficulty of convincing co-workers to attend social gatherings. Andy and Angela agree to hold their wedding at Schrute Farms, which gives Dwight another chance to try to woo Angela back. Pam and Jim spend all day on the phone together thanks to tiny headsets, so Jim hears when one of Pam’s art-school friends tries to convince her to stay in New York.
Title: “Business Trip”
Original Airdate: November 13, 2008
Title: “Frame Toby”
Original Airdate: November 20, 2008
Toby returns to the office from his time in Costa Rica, and Michael is extremely unhappy about it. He and Dwight conspire to get Toby fired, trying to goad him into sexually harassing Pam or assaulting Michael and eventually unsuccessfully framing him for marijuana possession using a bag of salad. Ryan dumps Kelly in an extremely condescending manner, which she takes in her usual oblivious way. Jim tells Pam that he bought his parents’ old house for them, and she seems dubious at first but eventually tells him that she loves it.