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A Streaming Guide To Michael Scott’s Most Significant Loves On ‘The Office’

Michael Scott wasn’t misunderstood. He really was a complete jerk in the early going of The Office, but the writers found a way to make him more relatable and even sympathetic by painting him as someone who was perpetually in search of love and constantly getting in his own way. We love Michael’s thorny path to a happy ending, so we wanted to look back at some of the most memorable episodes along the way while also debating the two most prominent loves of Michael’s life: Jan and Holly.

Which match was a better fit? It may not be as clear cut an answer as you assume.

The Deposition Season 4, Episode 12

When Jan’s wrongful termination lawsuit against Dunder Mifflin got nasty, Michael was called in to testify on her behalf where he tested the stenographer’s understanding of a good “That’s What She Said” joke and had his diary read aloud.

Jason Tabrys: There were several signs that Jan was toxic for Michael but this might have been the biggest alarm, completely and totally violating his sanctuary of thought to inch ahead in a legal battle that had the bonus of putting him in a very difficult position with his job.

Jessica Toomer: The truth is very complicated Jason. Jan was simply making sure that Michael remembered their relationship milestones correctly. She was clear with him from the beginning about their romantic status but with a man like Michael, she had to drill it into his head before he risked her million-dollar lawsuit. What woman hasn’t had to manage their doofus boyfriend every now and then? Also, what grown man keeps a diary? She did him a favor by shaming him in that legal battle.

Jason: Michael definitely needed to be managed but isn’t there a difference between that and being used? I feel like you believe Jan took the scorched earth approach under the auspices that a win would change both of their lives but isn’t it more likely that she would have blown her legal winnings on a pop-up candle shop and left Michael to eat his dollar menu dinner by himself?

Jessica: Candles are the fastest-growing product in the scent-aroma market. She made a calculated business decision with those winnings, sir. But yes, the way Jan manipulated Michael felt a little icky though I’d argue that Michael often revealed deeply personal information to their shared corporate overlords before this boardroom debacle. Is there really a difference between Michael sending photos of them in the Bahamas to the entire warehouse and this?

Jason: I mean, his act was sort of accidental but not really because it was born from him trying to conquest brag. These are both terrible people, at least in this stage of their existence.

Dinner Party Season 4, Episode 13

Who’s Afraid Of Virginia Woolf feels are activated as we watch the destruction of Michael and Jan’s already tentative hold on domestic bliss during a dinner party from hell.

Jessica: These were two people who were clearly not ready to cohabitate, especially in such a poorly-carpeted condo, but Jan got the short end of the stick here. There are hints as to what this place looked like before and I can only imagine the amount of mothering a man like Michael needs. When you crash into your glass patio door because it’s been cleaned for the first time in forever, you were probably living in filth.

Jason: I mean, none of this is untrue but the path to a fruitful cohabitation is compromise and respect and it doesn’t feel like that was the profile of their relationship. To be real, this was a fling that married a desperate need to feel loved (Michael) with a penchant for self-destructive tendencies (Jan) and then it had to level jump because Jan got too close to the fire, lost her job, and had no other option. Of course, it blew up, the ingredients were all wrong, but at the same time, it’s easy to see why they struggled to realize that when the situation masqueraded as a stable one until just a little pressure was applied.

Jessica: That’s fair. Neither seemed capable of giving the other the emotional support they needed. My only gripe is that this episode, as hilarious as it was, positioned Jan as the bad guy in the pairing — a trend that would continue for the rest of her time on the show. Up until then, the deposition debate aside, it felt like Jan, while high-strung and given to erratic mood swings, was also a level-headed executive who couldn’t believe she’d found herself attracted to someone like Michael Scott. Once they got together, there was a character shift that targeted her worst flaws.

Baby Shower Season 5, Episode 4

Jan surprised Michael by arriving at the in-office baby shower he threw her with a fully-birthed human butterball. Discovering that Michael had no emotional connection to the child pushed him to finally take the next step in his relationship with Holly.

Jason: It’s hard to argue that Jan wasn’t drawn as a worse person than Michael. Which is particularly clear when recalling this episode. Here, Jan reveals that she kept him at a distance from the birth of her child (though, why he was involved at all is still a question and an example of the writers trying to still tap into Melora Hardin’s specific magic after probably burning through the character). This is awful, but what’s worse is that she then tries to put Michael’s heart in a box, preserving him as an option by forbidding him from dating Holly, who he’s clearly connecting with on a higher level than he did with Jan.

Jessica: And by connecting you mean insulting her in front of the entire office to appease his ex-girlfriend and telling her she smelled “like old tomatoes?” Here’s the thing: Jan didn’t owe Michael anything when it came to that baby. She was kind enough to bring Astrid by, hang out with some ex-employees, and let Michael get some one-on-one time because she knew it meant something to him. (She may have also wanted that nap.) Michael is the one who assumed he needed to troll Holly publicly to make Jan happy, and he willingly did so. What’s worse, Holly let him.

Jason: And by “hang out with some ex-employees” you mean hold them hostage while feeding her ego. As for the theatrics between Michael and Holly, it’s a bit much and broad (as the show often was to a less endearing effect in later seasons), but where you see weakness in Holly’s willingness to be a pin cushion to help Michael maintain a connection to Astrid, because of how much the kid (inexplicably) meant to him, I see consideration and the starting embers of love. Aw, in other words.

Sex Ed Season 7, Episode 4

Prompted by the eruption of a cold sore on his face, Michael goes on a journey of romantic rediscovery, viewing some of his past flings through less than rose-colored glasses thanks to a series of deeply unsatisfying encounters with his deeply unsatisfied (and amply annoyed) ex-girlfriends.

Jessica: You’re too soft Jason. I worry about your naivete when it comes to office romances. Alas, things kind of nose-dive for Michael in that particular department after Holly leaves for Nashua. this episode really highlights Michael’s own failings when it comes to love. He’s so eager to settle down that he often settles for the wrong women, and pushes his better matches away with his alarmingly quick ability to fall madly in love with complete strangers — i.e. Holly. I don’t know if this episode really championed one relationship over the other so much as it proved Michael Scott needs to grow up a bit and figure out what he really wants in a life partner.

Jason: Going to ignore the character assassination attempt atop your answer. This is a middling episode for me but, as you point out, it’s still so important in establishing the final run for the character as he gains a measure of self-reflection. I guess the question is, while realizing that Jan, Pam’s mom, and the Caroline In The City lady weren’t a collection of great lost loves was vital, is the reignited focus on trying to make things work with Holly earned? I think it is, but I know you feel differently even though I don’t know why you are the way you are.

Garage Sale Season 7, Episode 19

Michael spent this episode brainstorming ways to propose to Holly, his HR rep. Setting himself on fire, chucking corpses off a building, they all made the list. But in the end, Michael kept it simple – sort of.

Jessica: This cold dead heart does not stir in the slightest at the thought of Holly and Michael rekindling their romance, and yet, that’s exactly what the show gave us in season seven. With “Garage Sale” we got a peek at this couple’s endgame and it felt bizarrely rushed. Having Michael abruptly propose to Holly and then announce he’s moving with her to Colorado gave me a bit of whiplash. It’s lovely that Michael would make that kind of sacrifice for her, but after their first break-up, when Holly felt like a seven-hour drive (3.5 hours if they’d agreed to meet halfway) was too much work, did she deserve that sacrifice?

Jason: It’s not the most forward-thinking response but I don’t know that I care. We never had the chance to really get to know Holly. She was nice enough and dorky enough to seem like a fit for Michael but the point was that the writers got to give Michael the reward he was looking for: someone who loves him for him. Looking at it through that lens makes it easier to say that Holly was the ideal partner for Michael even if she didn’t push him to be a better person, just a more satisfied one.

Jessica: I think there’s a balance to be struck between what Holly offered and what Jan brought to Michael. Holly was the easier choice, someone who didn’t ask Michael to examine his less-appealing traits or behaviors too much. It wasn’t just that she got his inappropriate sense of humor, she encouraged and fed into her worst impulses. (Personally, I’ll never forgive either of them for that PDA episode.) I think Jan, while combative and certainly sorting through her own issues, represented a chance for Michael to maybe improve himself. She curbed his childish antics a bit and had things lasted, maybe Michael would’ve become more assertive, more in-tune with what he wanted in that relationship. Jan was a strong woman but a strong woman can help build a stronger man. Holly will never do that for Michael. Plus, she didn’t appreciate Threat Level Midnight. Why are we even arguing this Jason?

Jason: There really is no coming back from that Threat Level Midnight atom bomb. But I will say that I agree, in real life, about the importance of a partner pushing us to be better. I live that, but in addition to nudging me toward being more upright and adult-like, I’m also allowed to be me. It’s about being your best self for and because of that partner, not the version that they want you to be. It just doesn’t work. And so, as you said, Michael’s perfect partner is probably someone who is a mix between Holly and Jan. I think the answer is clear: Michael’s perfect match really was the chair model.