Michael and Jan’s relationship throughout The Office was one of the most toxic and demeaning relationships on the show. Michael was a man looking for love with anyone who would love him back. Jan, on the other hand, was his superior and was anything but interested in Michael. But after her divorce, Jan gave into Michael and the two began dating.
It didn’t take long for Michael to realize the relationship wasn’t working but he would rather be in a bad relationship than be alone. They were doomed from the start. Luckily, both Michael and Jan found happiness when they ended their relationship but it was a wild ride to the finish line.
Season 1: Strictly Business
The first season of The Office was its shortest season but it did a good job of showing who all the characters were and who to pay attention to. Jan Levinson made a few appearances in season 1 (both physically and over the phone) where she was laid down the hammer as Michael’s boss. Michael was clearly attracted to Jan and tried showing off in front of her but it didn’t work on Jan. Fans could tell that Jan loathed being around Michael and was itching for the Scranton branch to close so that she wouldn’t have to deal with him anymore.
Season 2: A One-Night Stand That Could Have Gotten Someone Fired
It looks like all of Michael’s pickup lines worked in season 2 because Jan and Michael finally spent a night together after a successful business meeting with a huge client. Michael wouldn’t disclose if the two slept together but he did mention that they fell asleep together. The next day, Jan sounded like she wanted to pretend like it never happened and warned Michael to keep his mouth shut over it.
But in ‘Valentine’s Day,’ Michael showed off to the other branch managers by saying he slept with Jan. News got to the new CFO where the two had to have a serious meeting about their futures at Dunder Mifflin. But just as fans thought their weird relationship was done for good, she showed up to Scranton’s Casino Night in hopes of spending the night with Michael. When that didn’t happen, she left angry and drove back to New York.
Season 3: A Trip To Jamacia & The Start Of It All
After Jan was embarrassed on Casino Night, she went out of her way to make Michael’s job harder. She warned him that Dwight was gunning for his position, she was cold to him at the convention in Philly, and she asked Pam to take note of everything Michael did in a workday.
By ‘Branch Closing,’ Jan finally got her wish and tried closing the Scranton branch. It was hard for Michael not to take it personally and didn’t act maturely to the news. However, when Scranton stayed open and the Stamford branch closed, Jan’s hands were tied and she backed off from Michael. That is until he invited her to an all-inclusive resort in Jamacia over Christmas time… In ‘Cocktails,’ Jan and Michael were officially dating and handed their “love contract” into corporate.
Season 4: The Demise Of A Relationship
At the start of season 4, Jan was fired from Dunder Mifflin and living with Michael in his Scranton condo. The two went from being in a depleting long(ish)-distance relationship to living with each other in a matter of hours. They seemed loving in ‘Fun Run’ but the truth spilled out in ‘Money.’ Michael’s salary couldn’t afford Jan’s lifestyle and he was in serious debt. What’s worse is that Jan didn’t seem to care. Things got trickier in ‘The Deposition’ when Jan sues Dunder Mifflin for wrongful termination and Michael had to vouge for Jan. In the end, Michael defended Dunder Mifflin when he found out Jan stole his journal and used it against him for the deposition.
Their relationship came to an end in ‘Dinner Party’ when Jan and Michael’s differences ruined a sweet dinner party with friends. But their relationship didn’t stop there. In the season finale, Michael found out Jan was pregnant.
Season 5: Is Michael The Father?
It turns out that Michael wasn’t the father of Jan’s baby. Instead, she went to a high-end sperm bank while she and Michael were still together because she wanted a baby — just not Michael’s baby. Despite this, Michael took on the role of the child’s father and wanted to be a part of it. He and the office threw a baby shower for Jan but to their horror, she had already given birth and didn’t tell Michael about it. It reaffirmed that Michael had no place in that child’s life. After the shower, Michael dropped Jan and her baby and focused on a new relationship with Holly from HR.
Season 6: Michael Moves On Past Jan
Jan does not make an appearance in season 6. Now that she no longer works for Dunder Mifflin and is not dating or living with Michael, she was a thing in the past. Michael went on to date Holly until she was transferred, entered an odd relationship with Pam’s mom Helene, and dated a married woman named Donna. Michael compared every woman he dated to Holly, proving that his relationship with Jan no longer served him.
Season 7: The Resurrection Of A Fallen Relationship
The seventh season was Michael’s final season on The Office. After the demise of his relationships and remaining single, he felt compelled to confront his exes and talk to them not only about the alleged “herpes” on his lip but about their relationship. Holly noted that Michael had a tendency to romanticize everything and make their relationship seem like a bigger deal than it was. To see if that was true, he went to visit Jan at her new job to talk things through. Jan agreed that their relationship was awful and that they should have never dated. An angry Michael tells her he has herpes and he leaves the building. That was the final moment Michael and Jan were together on screen.
