All 27 episodes of season 5, with a short summary of each.
The office begins competing in a company-wide weight loss challenge over the summer. Jim and Pam adjust to their long-distance relationship while she attends art school in New York.
The weight loss competition intensifies as the office tries increasingly desperate strategies to win. Jim proposes to Pam at a gas station rest stop between Scranton and New York.
Holly conducts a business ethics seminar that backfires when Meredith admits she sleeps with a supplier in exchange for discounts and Outback Steakhouse gift cards.
Michael plans a baby shower for Jan, who arrives having already given birth to her daughter Astrid via sperm donor. Michael and Holly begin dating after Jan warns him to stay away from her.
The office is robbed after Michael and Holly leave the door unlocked following an after-hours tryst. Michael stages a charity auction with questionable items, including nonexistent Bruce Springsteen tickets.
Holly is transferred to the Nashua branch after corporate discovers her relationship with Michael, and they break up. Dwight applies to Cornell to get under Andy's skin.
Jim and Dwight receive suspiciously poor customer survey results, which turn out to be Kelly's revenge for them missing her party.
Michael takes Oscar and Andy on a business trip to Winnipeg, where Andy and Oscar bond and Michael spirals over Holly. Pam returns early from art school after failing a class.
Michael and Dwight scheme to get Toby fired after his return from Costa Rica, culminating in an attempt to frame him for marijuana possession using a bag of Caprese salad. Jim buys his parents' house for himself and Pam.
Oscar discovers a budget surplus that must be spent by the end of the day, splitting the office into factions fighting over a new copier versus new chairs. Dwight tricks Angela into a secret wedding ceremony at his farm.
Phyllis hosts a Moroccan-themed Christmas party where Meredith's hair catches fire from a candle. Phyllis uses her knowledge of Angela and Dwight's affair as leverage over Angela on the party planning committee.
Andy learns about Angela's affair with Dwight and challenges him to a duel in the parking lot. Both men ultimately dump Angela after discovering she was deceiving them both.
Michael goes undercover to spy on a small family-owned paper company and feels guilty about putting them out of business. The rest of the office passionately debates whether Hilary Swank is hot.
Dwight's simulated fire drill causes mass panic and Stanley has a heart attack. The staff is required to take a CPR training course where Dwight cuts the face off the practice dummy.
Michael agrees to let the office roast him to relieve workplace stress, but the staff's jokes cut deeper than expected. Michael retaliates with his own set of comebacks at the end of the night.
Michael tours other branches to lecture about Scranton's success, with Pam as his assistant, and visits Karen in Utica, who is now pregnant and married. Back in Scranton, Jim and Dwight run the party planning committee and botch Kelly's birthday.
A blood drive on Valentine's Day leads Michael to connect with a mysterious woman, but she disappears before he can get her number. He organizes a singles mixer to find her.
Michael hides Willy Wonka-style golden tickets in paper shipments for 10% discounts, but one major client receives all five tickets. He tries to get Dwight to take the blame until David Wallace praises the idea.
Charles Miner arrives as the new VP and immediately clashes with Michael by disbanding the party planning committee and canceling Michael's 15th anniversary party. Michael quits Dunder Mifflin in protest.
Michael serves out his two weeks' notice while trying to steal clients and recruit employees for his new company. Pam quits to join him after an argument with Charles.
Michael launches the Michael Scott Paper Company with Pam and Ryan operating out of a tiny closet in the office building. Jim struggles under Charles Miner, who forces him into a parking lot soccer game.
The startup struggles in cramped quarters but gains momentum after Pam makes her first sale. Charles asks Jim for a "rundown" and Jim spends all day trying to figure out what that means.
Michael and Dwight compete for the same clients after Dwight steals Michael's Rolodex. Andy, dealing with his broken engagement to Angela, seeks emotional support exclusively from Jim.
The Michael Scott Paper Company is going broke from unsustainably low prices, but Michael bluffs his way through buyout negotiations with David Wallace. He secures his old job back plus positions for Pam and Ryan.
Michael mediates disputes between the returning salespeople and the existing team over client assignments. The office takes Casual Friday too far, with Meredith's outfit being particularly inappropriate.
Michael opens a cafe-disco in his old Michael Scott Paper Company office space to boost morale under Charles's strict atmosphere. Pam and Jim consider eloping after getting swept up in the dancing.
Michael and Holly reunite and perform an awkward skit together at the Dunder Mifflin company picnic. Pam sprains her ankle during volleyball and discovers she's pregnant during the X-ray.