Overthinking the Office Part 4: Love is a Battlefield

When I need background noise while writing, more often than not I turn to The Office. And rewatching a show as often as I have means you have thoughts and opinions.

These are mine.

Supersized, strike-shortened

In season four, The Office gave in to one of the pit traps of success: overindulgence. After two exceptional seasons of comedy and heartache, they came out of the gate with a series of hour-long episodes, each meant to be split into two halves for syndication purposes. The problem was, not all of them had quite enough story to fill two chapters. Some work out okay: Fun Run, in which Michael organizes a charity run to cure rabies so that people will stop mocking him for running over Meredith with his car (it only makes sense to him and justifying it ruins the fun), only drags when Michael spends two minutes trying to invent a god to pray to in order to lift the curse he’s decided to blame for the whole “running over Meredith” thing. “Dunder Mifflin Infinity,” in which Michael acts out against changes to the company, is less successful. “Launch Party” and “Money” feel the most like separate episodes wedged together, but their individual halves work okay.

What makes this wave of double-sized episodes even more awkward, though, is that thanks to the 2007 Writers’ Strike (scourge of drama and comedy alike, killer of the incredible Pushing Daisies), these four episodes make up nearly half of season four’s runtime. That’s a lot of space taken up by four stories that have good bits (including our first visit to Schrute Farms) but sometimes struggle to stretch their A-plots out to 40 minutes.

The strike also means this is the second season with no Christmas episode. Which is a shame, since it was last year’s Christmas episode, Benihana Christmas, that made them think hour long episodes were a good idea.

The Rise and Fall of Ryan Howard

Season three ended with a three-way battle between Michael, Jim, and Karen for what turned out to be Jan’s job. Jim turned it down to return to Scranton for Pam. Karen doesn’t get it, but disappears shortly after (then turns up shortly after the hour-longs as the new branch manager in Utica). Michael was turned down, but upon hearing he wasn’t getting the job, asks to be withdrawn from consideration, because being turned down wouldn’t fit in his personal narrative. So who’s Michael’s new boss? Former temp Ryan Howard.

Ryan started as the rational outsider, the newcomer who, being less acclimated, could be tormented by the peculiarities of his new co-workers. As a temp in seasons one and two, as a salesman in season three, and as Kelly’s boyfriend, his sole bit was being trapped in a weird situation and trying to find an exit. But that bit has an expiration date. So it was time to try something new with Ryan: a complete power flip.

In season four Ryan goes from the lowest rung on the ladder to vice-president, and boss of the man who used him as a lackey for three years. Michael does some mystifying mental gymnastics to convince himself that the best pals/mentor-mentee relationship he’s always imagined still exists (or ever did), but Ryan fights him on it. It begins with simple power plays like making him sit with the other employees during a meeting, but hits its peak in Survivor Man, when Ryan invites every branch manager on a wilderness retreat, but not only doesn’t invite Michael… he invites Toby.

You can’t tell me he didn’t know what he was doing there.

Ryan’s big project, his vice-presidential baby, is Dunder Mifflin Infinity, the new sales website. It’s a good idea to begin with, despite Michael’s initial protests against Ryan changing the way business was done. It does pose some problems for the sales staff, though, as easy on-line ordering threatens their commissions (and usefulness), leading to Dwight having an entertaining man-vs-machine sales duel against the website. But when Ryan tries to turn it into the next Facebook, it becomes infested with child predators (somehow?) and identity thieves, and his desperate measures to save his baby and prove he deserves his Wunderkind label bring his meteoric rise to a shattering thud.

Does that track? Rise and thud? I mean the “fall” is kind of implied by the “thud,” isn’t it?

Along the way Ryan acquires an entourage of people shorter than him, gets hooked on drugs, tries to push Jim out of the company for speaking ill of DM:I to David Wallace, and finds the new Ryan Howard we’ll be spending seasons five to eight with. Ryan becomes determined to recapture his glory months as Dunder Mifflin’s youngest VP. He truly believes that he has the potential to become the next Steve Jobs or Mark Zuckerberg, but his season four failure makes him extremely anxious under any sort of pressure, and the nature of DM:I’s problems (thinking a paper company could be the new, cool social network) show that his ideas are often beyond the reach of his actual talents, whatever those may be. Beyond season four, he’s always searching for a new look, a new hook, a new way to prove to the world and himself that he is the bleeding-edge tech visionary he sees himself as.

Self-delusion, remember? Always comes back to that.

Coming together, falling apart

As I implied earlier, the big-cheer moment of season three’s finale was Jim coming back to Scranton and asking Pam out on their first real date. The first half of Fun Run keeps us in suspense as to how it went, or tries to… they each claim to be single (both to their co-workers and to the Documentarians, fresh off their summer break), but Kevin for one is not buying it, and is determined to prove that they are totally hooking up. Which the Documentarians swiftly do at the halfway point.

Producers from The Office went on to create and write for Parks and Recreation and Brooklyn 99, equally-if-not-more funny comedies that share a few common traits, but the relevant one just now is how they treat their most adorable couples. Leslie and Ben, Peralta and Santiago, Jim and Pam… they never get together easily, there are always obstacles, but when they have a couple that they and we know work, once they’re together, they stay together. See, when you’re good at your sitcom-writing job, you can make a power couple work just as well as a will-they-won’t-they maybe-couple. Even better, because they don’t wear thin as easily. So instead of going Ross-Rachel (a cautionary tale/definition of “diminishing returns”) and trying in vain to recapture the earlier magic by splitting them up and teasing a reunion, they find a new magic in letting us actually enjoy Jim and Pam’s love.

Besides, why split those two up when they have so many other couples to mess with for relationship drama?

Kelly and Ryan: The first thing Ryan did after accepting his promotion was break up with Kelly, moving their relationship from “She’s clingy, he’s awkward about it” to the first stage of the beautiful, horrible, addictive train wreck that could only blossom once Ryan began his journey from everyman to hipster douche. In the wake of being dumped, Kelly pulls out all of her “love is a battlefield” tricks on him, from “coincidentally” wearing something low-cut and lots of make-up for his first post-promotion visit to Scranton, to lying about being pregnant to score a date, to starting a relationship with Darrel and making sure to flaunt it in front of him.

“It’s like she only wants to hook up when Ryan comes around,” he later explains. “It’s gotten to the point where I get excited every time I see that little dude walk through the door.”

There’s not much to say about that couple, save for pointing out that Kelly’s drama queen games and attitude don’t work on Darrel, who’s built up a thick skin for upstairs-worker nonsense in his years of dealing with Michael. Also, while the writers were beginning to understand what a comedy weapon they had in Craig Robinson, Darrel doesn’t become a full member of the main ensemble until season six, so we don’t see him and Kelly together that often. As a couple, they really only exist as a plot point for the ongoing Ryan/Kelly drama.

Michael and Jan: Jan’s meltdown at the end of season three has not made for a happy relationship with Michael, not that either of them will admit it at first. Jan’s self-destructive spiral is far from over, and things come to an explosive end in Dinner Party. But that’s okay, because Michael has better things on the horizon. We’ll come back to that.

But first, let’s look at the worst relationship The Office ever produced.

Beyond toxic

Dwight and Angela work as a couple because they share the same unflinching sternness, the uncompromising commitment to repression as a lifestyle. But where “D” and “Monkey” go wrong is in another trait they share… see, they’re not cold and robotic about everything. They have their interests. But if something falls outside their narrow range of passions, their lack of interest or empathy borders on a psychopathy. Dwight is deeply passionate about beets, Battlestar Galactica, and bear safety, to name examples, and Angela’s lack of interest in any of that doesn’t cause problems, but Angela loves her cats. Her many, many cats. And Dwight, being a farmer and also being Dwight, has no use for any animal that doesn’t provide some form of utility. So when Angela asks Dwight to give the oldest of her cats, Sprinkles, her many, many medications, Dwight does the only thing that makes sense to him. He attempts to humanely put Sprinkles to sleep, but since this has nothing to do with farming or paper sales (his only true talents, whatever he believes), he bungles it and Sprinkles dies a slower, more agonizing death than he planned.

Of course Angela can’t forgive this. She loves her cats more than any human she has ever known, and Dwight murdered one of them. It can’t erase her love for “D” (oh dear lord that’s way too sexual I regret typing that so much), nothing can, but nor can she be with him. So their weirdly adorable, highly secretive love suffers a blow it will take most of the season to recover from. Worse, it opens the door for the least healthy, most toxic relationship the show ever produced.

Sure, Pam and Roy were less of a romance than Pam surrendering to convenience over passion, and sure, Michael and Jan’s relationship is a slow-motion train crash of emotional abuse fueled by delusion and self-destruction, but they’re both fairy tale romances next to Angela and Andy.

In an attempt to make it clear that Dwight’s attempts at reconciliation are unwelcome and futile, Angela publicly lets Pam know that she is both single and prepared to mingle, something Andy takes as an invitation to swoop in. His first attempts fail, but between a kind of adorable acapella rendition of “Take a Chance On Me” with help from his old college buddies on three speaker phones and a gift of a cat (the exact same cat Dwight tried to give her to make up for destroying Sprinkles, which is salt in Dwight’s wounds… also how is “destroy” the word we use for cat euthanasia, that is dark), Andy wins a date with her.

Seriously, that song move was pretty baller. If life hadn’t beaten the notion of using sitcom shenanigans as dating strategies out of me at a young age, I’d have considered using it myself. Andy has some game when he puts his mind to it. But that is the last moment in which there is anything sweet, romantic, or remotely healthy about these two.

But why? Why, though? Why does any of it happen? There is never a moment in their entire relationship when Angela demonstrates any sort of affection for Andy. His every romantic or playful gesture simply revolts her. And she’s suddenly way more repressed and Christian about, shall we say, physical intimacy than she ever was with Dwight. They never really explain why that is, why she was super fine with premarital sex when Dwight was involved but won’t even kiss Andy for the first few months. Because she’s actually dating him publicly, maybe? And so the relationship has to match to the morality standards she pretends to live by and attempts to inflict on everyone around her? Or maybe just because she simply isn’t actually into Andy at all and it takes a few months of dating before being kissed by him becomes tolerable.

Honestly that Andy and Angela become a couple at all is confusing, and the fact that they stay a couple as long as they do is beyond baffling, because the genesis of their relationship comes down to one thing. Andy admits in season seven that he’s bad at meeting people. His passion for yachting, acapella, and casually mentioning he attended Cornell don’t open a lot of dating doors, I guess. He dates three women in his seven years on the show, and two of them are co-workers (the third was a probable fix-up by Darrel). So it seems to me that Andy only went after Angela because she’s the most attractive single woman in his eyeline 40 hours per week. If Kelly didn’t work in the annex, he’d probably have gone after her instead, and he’d have been better off for it.

From there it can only be stubbornness. I cannot, for the life of me, imagine what either of them could possibly be getting out of this relationship, but Andy has been somehow conditioned to never give up or admit defeat (“Andy Bernard doesn’t lose contests. He wins them. Or quits them because they’re unfair.”), and breaking up with Angela because they’re an awful, awful match would be conceding that he made a mistake. So when Jim orchestrates a perfectly romantic moment in the season finale in order to propose to Pam, Andy ends up stealing his thunder by publicly proposing to Angela on a complete whim. Which she accepts to avoid awkwardness, I suppose. But then demonstrates her true feelings by immediately starting to bang Dwight again.

It always comes back to self-delusion. In this case, Andy’s delusion that if he keeps acting the part of someone in a blissful, fairy tale romance, it might eventually become one, despite the total lack of spark. Frankly, it’s clear that the writers had no interest in selling this relationship, because it wasn’t supposed to work. You’re not supposed to root for them to succeed or even care about Andy. From a story perspective, this relationship wasn’t even about Andy. Andy was only there to be a roadblock for Dwight and Angela. Hence Andy unknowingly twisting the screws by making Dwight his confidant for how the relationship is going, thinking that they’ve gone from rivals to friends, unaware that the rivarly has entered a whole new level.

We’ll come back to this arc and its failure as character growth next time.

Key Episodes

The Deposition and Dinner Party. Jan’s lawsuit against Dunder Mifflin was supposed to turn hers and Michael’s teetering-on-bankruptcy lives around, but when Michael is deposed, Dunder Mifflin fights back, and Michael and Jan’s every secret gets dragged out into the light. And worse for Michael, Toby’s there. This paves the way for The Office’s very own Who’s Afraid of Virginia Woolf, Dinner Party. After months of effort, Michael finally manages to hoodwink Jim and Pam into coming over for dinner, along with Angela and Andy. Which gives all four of them, plus party crashers Dwight and his former babysitter, front row seats to the detonation of Michael and Jan’s relationship.

And “Goodbye Toby,” for reasons I’ll get into below.


“Dunder Mifflin Infinity” does kick off Ryan’s plotline for the year, but it’s the weakest hourlong by far. And has one of Michael’s least-earned feelings of triumph.

Notable Guest Stars?

When Toby decides to move to Costa Rica after getting slightly too friendly with Pam (on whom he’s had a crush for, I don’t even know, at least a year and a half), corporate sends a new HR rep… our first veteran of The Wire, Amy Ryan as Holly Flax.

Holly Flax is, in simple terms, Michael’s dream girl. He falls for her the minute he speaks to her, she actually finds him funny, they are a perfect match. The day where Andy and Angela’s hopelessly terrible relationship unaccountably reaches the next level also put the pieces in play for one of the show’s best love stories… But well, that’s next season.

Author: danny_g

Danny G, your humble host and blogger, has been working in community theatre since 1996, travelling the globe on and off since 1980, and caring more about nerd stuff than he should since before he can remember. And now he shares all of that with you.

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