There are plenty of things Michael Scott does badly as regional manager of Dunder Mifflin. Maintaining professional boundaries has to be somewhere near the top of the list. This is a man who desperately wants the people working for him to be his family. He wants them at his parties. He wants to know about their relationships. He wants to participate in their personal lives whether they have invited him to or not. So maybe it shouldn’t be surprising that the Scranton branch eventually becomes a place where the distinction between coworker and romantic partner is about as clearly defined as Creed’s actual job responsibilities.

Over nine seasons, The Office gives us an astonishing number of workplace relationships. Some become marriages. Others implode spectacularly. A few are so forgettable that I’m occasionally surprised by them when I rewatch the series. Wait. Darryl dated Val? Oh, yeah.

The interesting thing is that I don’t think The Office necessarily presents workplace romance as a particularly good idea. If anything, the series spends nine seasons demonstrating exactly how complicated life can become when the person sitting twenty feet away from you is also the person you’re sleeping with, marrying, divorcing, cheating on, or desperately trying to convince that the two of you belong together. And nowhere is that more obvious than with the relationship that became the emotional center of the series.

Jim and Pam: The Love Story We’re Supposed to Love

Jim Halpert and Pam Beesly are clearly meant to be The Office’s great love story. And eventually, I like them together. It’s getting them there that bothers me.

From almost the beginning of the series, Jim is obviously in love with Pam. Not mildly interested. Not wondering whether maybe they could grab dinner sometime. The guy is gone. Everyone around them can see it, and I have a hard time believing Pam couldn’t. The problem, of course, is that Pam is engaged to Roy.

I know unrequited love happens. I also know that friendships can become complicated when one person develops feelings the other doesn’t share. Sometimes those feelings grow slowly enough that the person experiencing them doesn’t even recognize what’s happening until the friendship has already crossed into something emotionally complicated. But Jim is not subtle.

He spends the better part of two seasons waiting for Pam while she continues treating him as her closest friend and emotional confidant. She laughs at his jokes. She joins him in tormenting Dwight. She seeks him out when she needs someone who understands her. Meanwhile, she’s still wearing another man’s engagement ring.

That doesn’t make Jim innocent either. He knows she’s engaged, and he continues pursuing her anyway. He puts himself in the position of becoming the guy Pam turns to for the emotional support she isn’t getting from Roy, all while hoping that she will eventually recognize what the audience already knows. And eventually he just says it. “I’m in love with you.”

That confession at the end of Season Two finally forces Pam to confront something she has spent a long time pretending she doesn’t see. Jim kisses her, Pam ultimately calls off her wedding, and the series spends another season keeping them apart before finally allowing them to become a couple. The strange thing is that once they’re together, I like them considerably more.

Jim and Pam After the Chase

Once the writers stop asking us to wonder whether Jim and Pam will get together, they become a surprisingly functional television couple. That isn’t always easy to write. Television loves the chase because uncertainty creates story. Once the couple gets together, writers often panic. Suddenly the conflict that sustained the romance disappears, so somebody has to cheat, develop amnesia, secretly marry someone else, or discover that their new boyfriend is actually their evil twin from another dimension.

Thankfully, The Office mostly allows Jim and Pam to simply build a life. They get engaged. They marry. They have children. They become the people who understand each other well enough that a look across the office can function as an entire conversation. Then Season Nine deliberately starts pulling at the seams.

Jim becomes increasingly invested in Athlead, the sports-marketing company he helped establish in Philadelphia, while Pam remains in Scranton with their children. Jim’s ambitions begin changing what their marriage looks like without Pam feeling as though she has much say in the matter. Eventually, the emotional distance between them becomes serious enough that the documentary crew itself begins intruding into their lives through Brian, the boom operator.

I appreciated the idea behind that storyline more than I necessarily liked its execution. Relationships become difficult when people stop feeling heard. Jim sees an opportunity to finally do something with his life beyond selling paper, and that makes sense. Pam sees her husband making enormous decisions that affect their family without fully including her, and that makes sense too. What doesn’t always make sense is how unfamiliar these two suddenly seem with each other.

For people who spent years communicating through facial expressions across a reception desk, they become remarkably bad at having an actual conversation. Still, I’m glad the show challenged them. Their marriage survives because they eventually start listening again, and their ending feels earned precisely because the series lets us see that getting the girl isn’t the end of a relationship. You have to keep choosing each other after the cameras stop treating your romance like a fairy tale.

Michael and Holly: When Someone Actually Gets the Joke

If Jim and Pam are supposed to be the great love story, Michael and Holly might be the relationship I appreciate most for what it gives Michael. Holly Flax genuinely likes him. That sounds like an incredibly low bar, but look at Michael’s romantic history. With Holly, Michael finally meets someone who doesn’t merely tolerate his personality. She laughs at the same stupid things. She participates in his bits. She understands why an impression that makes everyone else in the office desperately search for an exit is somehow hilarious. For once, Michael isn’t performing for someone he desperately wants to impress. Holly is already laughing.

The frustrating part is how compressed their actual relationship sometimes feels. Michael is immediately smitten when Holly arrives in Scranton, but Jan’s pregnancy briefly pulls him back into her orbit. Once Michael and Holly finally begin dating, David Wallace discovers the relationship and transfers Holly to Nashua because of the company’s concerns about another office romance involving Michael.

Then Holly is gone for a long stretch of the series. By the time she returns to Scranton, she’s involved with A.J., leaving Michael in the uncomfortable position of waiting for someone who isn’t available. Eventually Holly and A.J. split, Michael and Holly reconnect, and before long Michael is proposing in an office filled with candles while the sprinklers soak everybody. Then they’re moving to Colorado.

Part of the speed is unavoidable because Steve Carell was leaving the series. Michael needed an ending, and giving him the family he had spent years desperately wanting was about as appropriate an ending as the show could have found. I just wish we’d gotten more time to watch him and Holly actually exist as a couple. Still, the emotional destination works. Michael spent years demanding that his employees become the family he didn’t have. Holly finally gave him the opportunity to build one of his own.

Dwight and Angela: Somehow This Works

Explaining Dwight and Angela’s relationship to someone who has never watched The Office would be an interesting exercise. “Well, they secretly dated. Then Angela agreed to marry Andy. But she continued sleeping with Dwight. Later she married a state senator who was actually having an affair with Oscar. Also Dwight once arranged for someone to deal with Oscar in a way that we probably shouldn’t unpack right now.”

And eventually you’d have to say: “Anyway, you’re going to be really happy when Dwight and Angela get married.”

Somehow, it’s true. Their relationship is deeply disturbing for large portions of the series. They’re secretive and manipulative. Dwight kills Angela’s cat because he believes he is ending the animal’s suffering, which is probably not covered in most couples-therapy workbooks. Angela cheats on Andy with Dwight while planning her wedding. None of these people should be allowed near a bridal registry. And yet there’s something fundamentally compatible about Dwight and Angela. They understand each other’s weirdness.

The show takes a long, ridiculous road to get there, but their eventual reconciliation works because neither one has to become somebody else to make the relationship function. By the time Dwight learns that he really is Philip’s father and proposes to Angela, their reunion feels less like the show forcing its original couple back together and more like two people finally admitting what everyone else has known for years. These two bizarre human beings belong together. I wouldn’t necessarily want them living next door. But I’m glad they found each other.

Michael and Jan: The Plasma Television of Relationships

Then we have Michael and Jan. If Jim and Pam demonstrate how complicated workplace romance can become, Michael and Jan demonstrate why Human Resources departments have policies. Their relationship begins with an enormous power imbalance. Jan is Michael’s superior at Dunder Mifflin, and neither of them is particularly good at separating the personal relationship from the professional one. As Jan’s life begins falling apart, their relationship becomes increasingly volatile until we arrive at one of the greatest episodes The Office ever produced. “Dinner Party.”

There may be no better demonstration of a relationship being held together by resentment, denial, and an incredibly small television. Everything about that evening is uncomfortable. Michael and Jan snipe at each other in front of their guests. Michael shows Jim and Pam the bench where he sleeps because Jan has taken over the bedroom. Jan makes Michael’s finances sound like an ongoing hostage situation. And then there is that plasma TV.

The relationship is funny because it is so obviously awful, but the humor never completely hides how unhealthy these two have become together. Michael constantly seeks Jan’s approval while also resenting the control she exercises over his life. Jan seems alternately embarrassed by Michael and dependent on him. They don’t bring out the best in each other. They locate the worst and hand it a megaphone. If there is any relationship on The Office more toxic than Dwight and Angela at their worst, Michael and Jan are strong contenders. At least Dwight and Angela eventually grow into something functional. Michael and Jan grow into a shattered Dundie.

Ryan and Kelly: Please Stop Calling This a Relationship

Ryan and Kelly are not a love story. They are a recurring incident. I don’t buy them as two people who could maintain a meaningful long-term relationship. I can absolutely buy them as two people who continue hooking up because neither one possesses the emotional maturity necessary to stop. That’s why they work as comedy.

Kelly desperately wants Ryan to be the boyfriend she has imagined. Ryan desperately wants whatever Ryan currently doesn’t have. When Kelly wants him, he wants freedom. When she begins moving on, suddenly Ryan discovers emotions. Their relationship survives primarily because dysfunction has remarkable endurance.

The finale takes that idea to its logical conclusion. Ryan and Kelly encounter each other again at Dwight and Angela’s wedding, immediately rediscover their attraction, and run away together despite both being involved with other people. Is that romantic? Absolutely not. Is it Ryan and Kelly? Completely.

I don’t need to believe they live happily ever after. I’m not convinced they make it through the weekend. But somewhere, someday, one of them will probably text the other at two in the morning. And the cycle begins again.

Andy and Erin: When the Sweet Guy Stops Being Sweet

Andy and Erin are more frustrating because I actually liked them in the beginning. Andy’s early attempts to woo Erin have a sweetness that works. Erin is quirky enough to appreciate Andy’s particular brand of weirdness, and there’s a period where it seems like the show may have found a relationship that allows both characters to become more likable.

Then Erin goes to Florida. She decides to remain there, and Andy drives down to win her back despite being involved with Jessica. That already requires some ethical gymnastics, but the show clearly wants us rooting for Andy and Erin. Fine. Then Season Nine happens.

Andy leaves Erin behind while he goes on a months-long sailing trip. He barely communicates with her, returns expecting everything to resume as though nothing happened, and generally behaves like someone who has forgotten that his girlfriend is an autonomous human being.

By the time Erin finally ends the relationship, I’m on her side. The problem is that I never became particularly invested in her replacement relationship with Pete. Or Plop, because apparently Andy gets naming rights. Pete is nice. He treats Erin better. Their relationship makes considerably more sense than whatever Andy and Erin had become. I just don’t care.

Maybe that’s because the show had already spent so much time trying to convince me Andy and Erin mattered. Maybe it’s because Pete arrives late enough in the series that there isn’t much time to become invested in him. Either way, Erin choosing herself and leaving Andy matters considerably more to me than Erin choosing Pete.

Everybody Else Who Dated Somebody Near the Copier

We could keep going. Nine seasons gave The Office enough romantic combinations to construct a relationship flowchart that would require its own conference room. Pam had Roy. Jim dated Karen. Erin dated Gabe. Darryl dated Val. Oscar became involved with Angela’s husband. Phyllis married Bob Vance, Vance Refrigeration.

And there are still more. But that actually reinforces the larger point. Dunder Mifflin is a workplace where personal and professional boundaries barely exist. Michael deserves plenty of blame for establishing that culture, but eventually everybody participates in it. These people work together all day. They go to one another’s weddings. They know each other’s families. They attend office parties that routinely become personal catastrophes. Of course some of them fall in love.

The show doesn’t necessarily tell us that dating a coworker is a great idea. It shows us that once those boundaries disappear, relationships become inseparable from the workplace itself. When Jim and Pam are struggling, they still have to work together. When Dwight and Angela are sleeping together behind Andy’s back, Andy is sitting a few desks away. When Michael and Holly fall in love, corporate management literally intervenes. There is no clean separation. Maybe that’s why these relationships work so well as stories.

Love in a Place That Sells Paper

For all its romances, The Office never really becomes a show about romance. It remains a show about people who happen to spend an enormous portion of their lives together. Some of those people fall in love. Some confuse attraction with compatibility. Some remain together long after every reasonable person would have fled the building. That feels appropriate.

I don’t love how Jim and Pam begin, but I like where they end up. Michael and Holly feel rushed, yet I’m happy Michael finally finds someone who laughs because she genuinely thinks he’s funny. Dwight and Angela somehow transform one of the most disturbing relationships on the show into one of its most satisfying endings. Ryan and Kelly are probably still breaking up as I type this.

Maybe that’s the real lesson The Office offers about workplace romance. There isn’t one version of it. Sometimes the person sitting near you really does become the love of your life. Sometimes dating someone from work creates a mess that follows you into every meeting and Christmas party. Sometimes you discover that the person you’ve been quietly flirting with for years is exactly who you thought they were. And sometimes your girlfriend throws a Dundie at your television. Love is complicated. Especially when you still have to see each other Monday morning.

Which Office relationship worked best for you? Did you root for Jim and Pam from the beginning, or do you think their early relationship was more complicated than the show sometimes wanted us to admit? Let me know in the comments!