"The Office" Season 5 Episode Guide

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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. 

Episode 1

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.

Episode 2

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.

Episode 3

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.

Episode 4

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.

Episode 5

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.

Episode 6

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 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.

Episode 7

Title: “Business Trip”
Original Airdate: November 13, 2008

Michael, Andy, and Oscar take a business trip to Winnipeg to meet with a client. Michael hooks up with a concierge to try to forget his heartbreak over Holly, while Andy attempts to play wingman for Oscar and ends up drunk-dialing an angry Angela, who resets their relationship to first base. Pam fails out of one of her art-school classes, but rather than spend three more months in New York to make it up, she comes home to Scranton to be with Jim. Kelly and Ryan hook up, but he seems less than thrilled about the return of their relationship once it becomes clear that Darryl is in no way jealous.

Episode 8

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.

Episode 9

Title: “The Surplus”
Original Airdate: December 4, 2008

Oscar discovers a budget surplus that must be spent by the end of the day, and the Dunder-Mifflin employees divide into two factions over how it should be used: One group wants to buy a new copier, while the other wants new chairs. This pits Jim and Pam against each other when Jim supports the copier. Eventually, Michael discovers that he can get a bonus if he returns the surplus, but the staff overrules him in favor of the chairs. Out at Schrute Farms, Dwight humiliates Andy while going over Andy and Angela’s wedding plans, and then tricks Angela into a possibly binding wedding ceremony. Her response is to tell Dwight off and then plant a huge, completely non-erotic kiss on Andy.

Episode 10

Title: “Moroccan Christmas”
Original Airdate: December 11, 2008

Phyllis plans a Moroccan-themed Christmas party and uses the opportunity to bully Angela into becoming her slave, threatening to reveal Angela’s affair with Dwight if Angela doesn’t do everything Phyllis says. Eventually, Angela refuses, and Phyllis tells the whole office -- except Andy, who’s in another room and remains oblivious. At the party, Meredith gets drunk and sets her hair on fire, which leads Michael to stage a disastrous intervention for her, and then drag her off to rehab, both of which prove unsuccessful.

Episode 11

Title: “Duel”
Original Airdate: January 15, 2009

Michael finally tells Andy about Angela’s affair with Dwight, and Andy and Dwight agree to fight a duel to determine who wins Angela’s love. Their rather pathetic face-off, with Dwight brandishing arcane weapons and Andy pinning Dwight with his car, doesn’t result in a winner, but each ends up so disappointed in Angela that neither wants her after the duel is over. Meanwhile, Michael heads to corporate, where David Wallace wants an explanation for why the Scranton branch is doing so well, but of course, Michael has no clue.

Episode 12

Title: “Prince Family Paper”
Original Airdate: January 22, 2009

David Wallace sends Michael to spy on a family-owned rival paper company, and Michael and Dwight manage to score some serious inside info by posing as a potential customer and a potential new employee, respectively. Michael is conflicted about reporting the info and screwing over the friendly family that owns the company, but Dwight convinces him to be ruthless. While Michael and Dwight are gone, the rest of the office holds an elaborate debate to determine whether or not actress Hilary Swank is hot.

Episode 13

Title: “Stress Relief”
Original Airdate: February 1, 2009

Dwight’s staged fire (to demonstrate the office’s lack of preparedness) causes Stanley to have a heart attack, so to reduce office stress Michael decides to hold a roast (of himself). Everyone does their best to insult Michael, and eventually, he takes it to heart. But he bounces back in his usual oblivious way, pathetically “roasting” his co-workers himself. Jim and Pam deal with the impending divorce of Pam’s parents, and Andy confuses their hushed conversations about it for keen analysis of a movie-within-the-show starring Jack Black, Cloris Leachman and Jessica Alba in a lame bit of stunt casting.

Episode 14

Title: “Lecture Circuit”
Original Airdate: February 5, 2009

Michael is asked to tour the other Dunder-Mifflin branches to talk about his strategies for sales success and takes along Pam as his assistant. In Utica, Michael’s lecture is a disaster as expected, but Pam encounters a newly married and pregnant Karen, and the two seem to put the past behind them. This inspires Michael to propose a detour so that he can achieve closure with Holly. Back in Scranton, new Party Planning Committee co-chairs Jim and Dwight have forgotten Kelly’s birthday, so they work to make up for it by planning a thoroughly pathetic celebration. And newly single Andy awkwardly attempts to woo an unreceptive client.

Episode 15

Title: “Lecture Circuit Part 2”
Original Airdate: February 12, 2009

Michael and Pam take their lecture tour to Nashua to confront Holly, but she turns out to be away on a retreat. Instead, Michael encounters Holly’s new boyfriend and melts down during his lecture. Later, he finds a letter on Holly’s computer that she wrote to him but never sent, and has Pam read it. Pam tells Michael that Holly still has feelings for him. Back in Scranton, Jim and Dwight continue to plan Kelly’s pathetic birthday party, and eventually, find a way to make her happy. And Angela disturbs everyone with her excessive attention to and affection for her new cat.

Episode 16

Title: “Blood Drive”
Original Airdate: March 5, 2009

Valentine’s Day makes Michael depressed about his break-up with Holly, so he organizes a mixer for all the singles in the office, and invites people from surrounding businesses. Michael hopes to reconnect with a woman he shared a moment with while donating blood, but she never shows up. Non-singles Jim and Pam share a couples’ lunch with Phyllis and her husband Bob, which goes very well until Phyllis and Bob sneak off to have sex in the bathroom, making Jim and Pam extremely uncomfortable.

Episode 17

Title: “Golden Ticket”
Original Airdate: March 12, 2009

Michael comes up with the idea of inserting five Willy Wonka-esque “golden tickets” into random paper shipments, giving customers 10 percent discounts. But when one major client gets all five, the plan backfires, and Michael tries to get Dwight to take the fall. Dwight goes for it, but he ends up getting credit when things turn back around. Michael can’t accept that, and eventually, no one comes out looking good. Meanwhile, Andy, Jim, and Pam give Kevin conflicting advice about how to approach the woman he met at the singles mixer, and he finally just ignores them and asks her out directly.

Episode 18

Title: “New Boss”
Original Airdate: March 19, 2009

New regional vice president Charles Minor (Idris Elba, "The Wire") comes to Scranton and immediately shakes things up by not tolerating any of Michael’s tomfoolery. Seeing Michael for what he truly is, a terrible manager, Charles cancels Michael’s 15th-anniversary party, disbands the party-planning committee and implements sensible office policies. Jim, dressed in a tuxedo to mess with Dwight, also ends up looking foolish in front of Charles. Michael, fed up with being undermined, goes to New York to complain to David Wallace, but even after being placated, he decides to quit.

Episode 19

Title: “Two Weeks”
Original Airdate: March 26, 2009

After giving his two weeks’ notice, Michael goofs off until he realizes that he has no plan for after he leaves Dunder-Mifflin. He impulsively decides to start his own paper company and goes around the office attempting to recruit people for this new venture, but no one takes him up on the offer. When Charles finds out what Michael’s doing, he orders Michael out of the office immediately. After spending the entire day learning how to use the new copier and then feeling unappreciated, Pam also impulsively quits, to join Michael in his ill-advised new business.

Episode 20

Title: “Dream Team”
Original Airdate: April 9, 2009

Michael and Pam struggle to start the Michael Scott Paper Company, as Michael first is overwhelmed, and Pam later has serious doubts. They recruit Ryan but fail to bring in Michael’s former telemarketing co-worker Vikram or to secure seed money from Michael’s grandmother’s investment club. Things do turn around a bit when Michael secures office space in a tiny utility room in the same building as Dunder-Mifflin. At Dunder-Mifflin, everyone tries to kiss up to Charles by pretending to love his favorite sport, soccer, which ends up backfiring for Jim.

Episode 21

Title: “The Michael Scott Paper Company”
Original Airdate: April 9, 2009

Michael, Pam, and Ryan have a stressful first day in their new office, where they bicker with each other, stage a pathetic pancake luncheon as their launch party and nearly decide to give up on the entire endeavor. By the end of the day, though, they make one sale, and things don’t seem so bad. At Dunder-Mifflin, Jim continues to have trouble connecting with Charles, who asks Jim to prepare a report he isn’t familiar with. Dwight and Andy test their newfound friendship when they compete for the affections of the new receptionist.

Episode 22

Title: “Heavy Competition”
Original Airdate: April 16, 2009

Dwight is secretly passing insider information about Dunder-Mifflin to the Michael Scott Paper Company, but after receiving praise for his salesmanship from Charles, he decides to put an end to it. He and Michael then find themselves engaged in a brutal competition to steal or retain key accounts. Even Dwight’s various acts of sabotage can’t keep Michael from scoring a meeting with one of Dwight’s biggest clients. At Dunder-Mifflin, Jim starts messing with Andy after Andy implies that Jim might be unhappy in his relationship with Pam.

Episode 23

Title: “Broke”
Original Airdate: April 23, 2009

Dunder-Mifflin continues to lose clients to the Michael Scott Paper Company because Michael is offering drastically reduced prices. But when Michael learns that his discounted rates will leave his company bankrupt in mere weeks, he jumps at the chance for a buyout from Dunder-Mifflin, and he, Pam and Ryan all return to the company, with Pam now working as a salesperson. Charles looks foolish in front of David Wallace for relying on Dwight over Jim and leaves Scranton humiliated, with Michael back in charge.

Episode 24

Title: “Casual Friday”
Original Airdate: April 30, 2009

With Michael, Ryan, and Pam back at Dunder-Mifflin, there’s a bit of tension as Michael assigns Ryan and Pam all the clients they stole while at the Michael Scott Paper Company. The other salespeople (save Jim, who stays out of it by hanging out with Creed) nearly stage a coup, and Michael ends up giving them their clients back. That leaves only enough clients for one more salesperson, so Ryan is downgraded back to his old temp job. Meanwhile, a number of employees go too far with the looseness of casual Friday, and Toby decides to shut it down.

Episode 25

Title: “Café Disco”
Original Airdate: May 7, 2009

Michael sets up a stereo and an espresso machine in the vacant Michael Scott Paper Company office and tries to entice the staff to join him for coffee and dancing. At first, he has trouble convincing people, and Phyllis hurts her back when she’s the only one to join him. But then Kelly and new receptionist Erin get things started, and soon the whole office is dancing the day away. Pam and Jim plan to sneak away for a quickie wedding, but while dancing, they realize that they really want a big party for their nuptials.

Episode 26

Title: “Company Picnic”
Original Airdate: May 14, 2009

At the annual Dunder-Mifflin company picnic, Michael runs into Holly and her new boyfriend. Michael and Holly team up for an awful Slumdog Millionaire parody sketch about the history of Dunder-Mifflin, during which they accidentally reveal the closing of the Buffalo branch. They don’t rekindle their romance, but they do share a few meaningful moments, which makes Michael happy. Jim and Pam get caught up in the volleyball tournament, which brings out Jim’s renewed rivalry with Charles Minor. A minor injury sends Pam to the hospital, where she discovers she’s pregnant.