For all the wholesome romances in The Office — from Jim and Pam to Dwight and Angela to Phyllis and Bob Vance — there was one romantic coupling that was decidedly unwholesome. Before Michael found his true soulmate (or “soup snake”) in Holly Flax, he had a ridiculously toxic on-and-off romance with his corporate superior Jan Levinson, who initially couldn’t stand him.
Throughout the first few seasons of The Office, Jan gradually fell for Michael and, after a fateful trip to Sandals, Jamaica, she trapped him in a cycle of psychological torment. These are the greatest episodes exemplifying Michael and Jan’s terrible relationship.
7 Cocktails (Season 3, Episode 18)
Michael gets a little carried away when Jan asks him to sign some documentation to acknowledge their relationship as a corporate formality in season 3’s “Cocktails.” Much to Jan’s chagrin, Michael calls the form a “love contract” and goes around David Wallace’s cocktail party telling as many guests as he can that he’s sleeping with Jan.
However, due to Jan’s self-destructive tendencies, the more Michael embarrasses her, the more attracted to him she becomes. As the official beginning of Michael and Jan’s tumultuous relationship, “Cocktails” ominously foreshadows all the terribleness to come.
6 Women’s Appreciation (Season 3, Episode 22)
The sordid behind-the-scenes details of Michael and Jan’s relationship come to light in the season 3 episode “Women’s Appreciation,” in which Michael takes all his female employees out to the mall after Phyllis is flashed in the parking lot.
While eating in the food court, Michael shares that Jan sometimes ignores their safe word during sex and forces him to dress as a schoolgirl. When Michael realizes he’s unhappy in his relationship, Pam encourages him to end it. The episode culminates in a hysterically awkward situation as Jan walks into Michael’s office while he’s in the middle of leaving a breakup voicemail on her phone.
5 The Client (Season 2, Episode 7)
Tim Meadows guest-stars as a major potential client that Michael and Jan meet at Chili’s in the season 2 episode “The Client.” While Jan is initially humiliated by Michael’s attempts to joke with the client, she warms to him when the client actually responds to it.
This is the episode in which Jan first found herself becoming attracted to Michael. She realizes she may have underestimated his intelligence when she sees his skills as a salesman.
4 The Deposition (Season 4, Episode 12)
Jan sues Dunder Mifflin for wrongful termination in season 4’s “The Deposition,” and gives Michael carefully prepared lies to tell during the hearing. However, Michael feels betrayed when he learns that Jan has admitted his secret diary as evidence in the deposition. Based on Michael’s language describing Ryan, the lawyers assume he’s another one of Michael’s lovers, which makes Toby laugh hysterically.
Michael has a right to be mad, but as Jan points out, he did share a naked picture of her with the entire company (albeit accidentally). Jan’s betrayal of Michael in “The Deposition” sets the stage for the death of their relationship in the next episode, “Dinner Party.”
3 Back From Vacation (Season 3, Episode 12)
After Michael’s girlfriend Carol breaks up with him before their trip to Sandals, Jamaica, Michael makes a mysterious call to invite somebody else. Season 3’s “Back from Vacation” reveals that he invited Jan, as he comes back with a picture of her sunbathing topless next to him.
Michael lands in a world of trouble when he accidentally emails the photo to the entire company while trying to send it to Todd Packer. Darryl has it blown up and posted on the wall of the warehouse, which makes Jan furious when she arrives to have a word with Michael.
2 Money (Season 4, Episodes 7/8)
The season 4 two-parter “Money” takes place after Jan has been fired from her job at Dunder Mifflin and moved into Michael’s condo, where she promptly started redecorating with Michael’s money. All these extra expenses — which Jan shrugs off with the classic mantra, “It costs what it costs” — force Michael to take on a second job at a telemarketing center.
The episode’s most hilarious moment is its climax, in which Oscar reviews Michael’s finances and freaks him out so much that he runs down to the railyard and tries to hitch a ride on a passing freight train.
1 Dinner Party (Season 4, Episode 13)
Without a doubt, the greatest Michael and Jan episode — and maybe the greatest episode of the whole series — is season 4’s “Dinner Party,” in which they invite Jim and Pam, Andy and Angela, and Dwight and his old babysitter over for dinner. This is one of the show’s most excruciatingly cringe-worthy episodes because Michael and Jan do everything in their power to make their guests uncomfortable.
“Dinner Party” culminates in Michael and Jan’s long-awaited breakup, as Jan throws a Dundie at Michael’s tiny plasma-screen TV during a heated argument and their neighbors call the cops. From Hunter’s “That One Night” demo to Serenity by Jan, this episode is filled with iconic moments.
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