Arguably in the running for TV’s worst couple, Michael Scott and Jan Levinson endured a turbulent on-and-off relationship across multiple seasons of The Office. It began as a one-off fling, but before too long, they were living together. No matter how many times Michael accepted that he wasn’t happy with Jan and tried to break things off with her, he always went crawling back.
And anyone – including the show’s other characters – could see that their relationship was toxic from the beginning. So, as cringe-inducing as it might be, here are the 10 most important moments in Michael and Jan’s relationship.
Their First Kiss
In season 2’s “The Client,” Jan realizes she may have underestimated Michael when she sees him charm a potential client at Chili’s and land a branch-saving account.
Outside the restaurant, a few drinks deep, she kisses Michael, then invites him back to her hotel room, where they spend the night making out. And so it begins.
Michael Accidentally Emails A Topless Photo Of Jan To The Whole Company
When Jan takes Carol’s place in Michael’s vacation to Sandals, the understanding is that the trip will remain a secret and they won’t enter into a relationship. However, in his attempts to send a topless photo of Jan from the trip to Packer to prove that it really happened, Michael accidentally sent the photo to everyone at Dunder Mifflin.
Before too long, the photo was blown up and hanging in the warehouse. Despite being mad at Michael, Jan can’t resist kissing him while she’s telling him off.
Michael Leaves Jan A Breakup Voicemail As She Walks In The Room
After having his eyes opened by an in-depth discussion with the women of the office in which he realizes he’s unhappy with Jan, Michael calls her and leaves a voicemail in which he breaks up with her.
However, midway through the message, Jan walks through the door and invites Michael out on a date. Then, she receives the voicemail in front of him.
Jan’s Breast Augmentation Convinces Michael To Take Her Back
When Jan comes into the office to win back Michael, his co-workers convince him not to let her manipulate him, and to stand strong.
However, when he sees that Jan has undergone breast augmentation surgery, he immediately changes his mind and takes her back.
Jan Decides To Move In With Michael
In the season 3 finale “The Job,” when Michael interviews for a corporate job and David Wallace tells him he’s interviewing to replace Jan, he accidentally tells Jan and she confronts David about it.
On the drive back to Scranton, Jan decides to move in with Michael and makes focusing on their relationship (and making candles) her new self-appointed job.
Jan’s Spending Forces Michael To Take A Second Job
In the two-part episode “Money,” Jan’s reckless spending of Michael’s money forces him to take a second job as a telemarketer. His work as a telemarketer begins to affect his work at Dunder Mifflin, and vice versa.
Eventually, Michael boldly declares bankruptcy in front of the office and, after Oscar takes a look at his books, impulsively runs toward a passing freight train with the intention of skipping town.
Jan Admits Michael’s Journal As Evidence In Her Deposition
When Jan was fired from Dunder Mifflin, she was determined to have it ruled wrongful dismissal and receive compensation, so she brought in Michael to testify in her deposition.
He memorized testimonies to defend her and did everything she asked, so he’s heartbroken when, in the middle of the deposition, it’s revealed that Jan admitted his personal journal as evidence.
Jan Throws A Dundie At Michael’s Plasma-Screen TV
Many fans of The Office consider the season 4 installment “Dinner Party” to be the show’s greatest episode. As Michael and Jan invite Jim, Pam, Andy, Angela, and later Dwight and his old babysitter over for dinner, there are a ton of memorable moments, from the video camera in the bedroom to the tiny plasma-screen TV on the wall.
Later in the night, as Michael and Jan break into an explosive argument, Jan grabs one of Michael’s Dundies and throws it at the TV, cracking the screen.
Michael Offers To Father Jan’s Baby
When Michael discovers that Jan went to a sperm bank in order to get pregnant, he offers to father the child. Although Jan’s uncomfortable with Michael being her baby’s father, she does like the idea of having someone to go to the classes with.
So, she invites Michael to the classes and, in true Michael fashion, he tells everyone in the office that he is the biological father of Jan’s child.
Michael Chooses Holly Over Jan
In the episode “Baby Shower,” Michael is dismayed to discover that Jan already has the baby and she didn’t call him when she went into labor. When Michael holds Jan’s baby, who he offered to help raise, he feels nothing.
Jan tells Michael not to date Holly, which only reaffirms his feelings for Holly. He goes into the annex and hugs Holly, which makes him realize that she’s the one he’s supposed to be with.